Home Vacation Rentals By Owner In Healdsburg, CA

Showing 20 Of 227 Vacation Rentals
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Exceptional(50)

$1322.77

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Private Vacation Home

Luxury Home in Healdsburg with a Private Pool plus complimentary wine tastings.

Healdsburg, California, United States

Decanter is a premium vacation rental that’s eight minutes away from downtown Healdsburg and set in four acres of lush greenery with sweeping views of the wine country. Renowned wineries like Mauritson, Lambert Bridge, Ridge, Amista, and Dry Creek Vineyards, to name a few, are a short drive from Decanter.brbrDecanter has well-appointed living spaces that include three luxurious bedrooms, a family room, a dining area that serves as a focal point of the space, and a game room. brbrA gourmet kitchen allows guests to prepare meals, and is stocked with a wide variety of pantry essentials, and premium kitchen tools and appliances. Prepare your meals while enjoying panoramic vineyard views.brbrThe poolside dining area offers some of the best views of the wine country, and the pool is always within reach for an afternoon splash. brbrThree bedrooms, with flexible accommodations in the large game room, make the Decanter a prime location for couples and family groups, alike.brbrDecanter is equipped with hi-speed internet, which makes working from home a breeze or streaming your favorite shows on one of our four Smart TVs.brbrDecanter also includes a Tesla charging station, a mini-gym with a Peloton.brbrComplimentary wine tastings can be arranged at three nearby wineries. Please inquire when booking.brbrNote: Outward facing security cameras (driveway, garden and pool), as well as a decibel monitoring sensor (inside/outside), are installed to ensure compliance with quiet hours (9pm - 7am).
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Exceptional(13)

$996.0

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Private Vacation Home

Wine Country Estate: Pool, Spa & Vineyard Views

Healdsburg, California, United States

Luxury wine country estate on 9 private acres with stunning vineyard views, just 8 minutes to downtown Healdsburg Plaza. Olympic-size pool & spa. Large 3-bedroom main residence plus a separate and private 680sf guest cottage. Gourmet kitchen for group gatherings. Grand living room and fireplace. Multiple outdoor entertaining areas. World-class wineries and 140+ tasting rooms, Michelin-starred restaurants, Russian River & gorgeous hikes are minutes away. Your complete wine country escape.brbrMessage us on Social Media at Inspired in Sonoma for Inspiration and Tips.brbrWelcome to your wine country sanctuary—a luxury Healdsburg retreat where rolling vineyard views meet resort-style living on nine private acres. This is where your story begins: sunrise coffee overlooking endless grapevines, afternoons by the Olympic-size pool or in the game room, evenings gathered around the fireplace sharing the day`s wine-tasting adventures, and nights watching films in the movie room or lounging under star-filled Sonoma skies.brbrYour estate features a beautifully appointed main home plus an 680 square-foot private guest cottage with private deck and kitchenette, offering the perfect balance of togetherness and retreat for groups of friends, multi-generational families, couples traveling together, or anyone seeking the ultimate wine country experience.brbrYOUR WINE COUNTRY HOMEbrStep into the heart of the home—a stunning gourmet kitchen designed for culinary adventures and lazy morning gatherings. With expansive countertops, professional-grade appliances, and space for everyone to contribute to meal prep while sharing stories, this is where memories are made. The open flow connects seamlessly to the inviting living room, where a grand fireplace anchors the space and floor-to-ceiling windows frame captivating vineyard panoramas.brbrThe main residence offers thoughtfully designed bedrooms, each a peaceful sanctuary with views that remind you exactly where you are: the heart of California`s most celebrated wine region. Each master suite includes en suite bathroom + Jacuzzi tub. brbrYOUR PRIVATE WINE COUNTRY RESORTbrStep outside and discover your personal playground. The Olympic-size swimming pool sparkles in the Sonoma sunshine, perfect for morning laps or afternoon lounging, while the spa invites evening soaks while vineyard sunsets paint the sky gold and rose. Multiple outdoor living areas, from intimate conversation nooks to expansive entertaining spaces, ensure everyone finds their perfect spot.brbrNine acres of countryside provide the peace and privacy you seek. Yet you`re just eight minutes from downtown Healdsburg`s renowned Plaza, where Michelin-starred restaurants, boutique tasting rooms, artisan shops, and the vibrant farmers market await.brbrYOUR HEALDSBURG ADVENTUREbrThis isn`t just about where you stay—it`s about experiencing everything that makes Healdsburg extraordinary. Begin your mornings cycling through Alexander Valley`s vineyard-dotted roads or hiking Armstrong Preserve Redwood Forest. Spend afternoons exploring over 140 nearby wineries, from legendary estates to intimate family operations where winemakers pour their own creations. As evening approaches, secure reservations at celebrated restaurants like SingleThread or Valette, where farm-to-table cuisine perfectly complements the region`s exceptional wines. Healdsburg`s celebrated events unfold throughout the year: the legendary Wine & Food Experience in May, harvest crush festivities in fall, intimate winter jazz performances, the vibrant Farmers Market year-round. Whatever brings you to wine country, this estate serves as your luxurious home base for every adventure.brbrYOUR PERFECT GROUP GETAWAYbrThis is more than a vacation rental—it`s your gateway to the wine country lifestyle, where every detail has been considered and every moment invites you to slow down, savor, and celebrate. The vineyard views are calling. The private resort is ready. The adventure begins now.brbrBook your escape to wine country`s most coveted destination retreat with breathtaking vineyard views! brbr***Please note***brSwimming pool can be heated up to 83 degrees for a fee of $150 per day with a 3 day minimum.brIf you would like to have the pool heated, please contact Kharis at least two weeks in advance of your stay to ensure this can be accommodated brPool is 60x14.5 feet brbrWi-FibrWi-Fi at this property is radio wave Wi-Fi and has speeds between 35 mbps and 80mbps.brbrFull access to all areas with the exception of locked room in garage.brbrAvailable by Airbnb app or by personal phone as needed.brbrPrivate Country Property in the hills with Vineyard ViewsbrbrYou will need to drive your car here and wherever else you need to go. Uber and Lyft are available but can be unreliable.brbrThe views from the deck are amazing. Wine Country at its finest.
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Exceptional(29)

$722.4

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Private Vacation Home

Healdsburg Wine Country Retreat | Hot Tub, Bocce, Vineyard Views

Healdsburg, California, United States

Located in Dry Creek Valley just minutes from Healdsburg Plaza, this modern wine country retreat is ideal for guests who enjoy indoor–outdoor living, shared meals, and relaxed evenings. The home sits on a half-acre with vineyard and rolling hill views and features a hot tub, bocce court, large deck, and chef-style kitchen with an oversized island seating six.brbr• 5 minutes to Healdsburg Plaza restaurants, tasting rooms, and shoppingbr• 10 minutes to dozens of Dry Creek and Alexander Valley wineriesbrbrThis home is best suited for guests who value thoughtful design, outdoor space, and gathering around food and wine.brbrHOME HIGHLIGHTSbrbr• Expansive outdoor space with hot tub, bocce court, redwood deck with string lights, outdoor dining in the yard, and Weber grillbr• Modern kitchen designed for wine-country dining with double oven, wine fridge, and Moccamaster coffee barbr• Oversized kitchen island seating six, designed for cooking and gatheringbr• Three bedrooms with king beds, Casper mattresses, and premium linensbr• Primary suite with spa-style bathroom, waterfall shower, double vanities, and direct deck accessbr• Fully fenced, dog-friendly yardbr• Vineyard and rolling hill views throughout the propertybr• Smart TVs in all bedrooms and living room with streaming servicesbr• Peloton bike and free weightsbr• Fast fiber Wi-Fi and dedicated workspace with extra monitorbr• Level 2 EV chargerbr• Easy access to Dry Creek Valley, Alexander Valley, downtown Healdsburg, the Russian River, and the coastbrbrWHAT GUESTS LOVEbrbrGuests often mention how welcoming the home feels and how easy it is to settle in:brbr“We have been staying in the Healdsburg area via VRBO for years and this is our favorite house yet. Minutes from town, clean, well equipped, and comfortable with king beds in every room. The backyard was incredible and our dog loved it.”br— Oscarbrbr“I cannot fully express how much we loved our stay. The location is amazing, close to everything. The house is beautiful and comfortable, but the backyard and views were the highlight.”br— KeeleebrbrBEDROOMS & BATHROOMSbrbrThe primary bedroom offers vineyard and rolling hill views, a king bed, and direct access to the deck—perfect for morning coffee as the fog lifts. The ensuite bathroom features Zellige tile, dual vanities, and a waterfall shower.brbrThe additional bedrooms also feature king beds, modern furnishings, and smart TVs. The second bathroom includes a shower/tub combo, and on-demand hot water ensures comfortable showers. Hair dryers, toiletries, and makeup wipes are provided.brbrKITCHEN & LIVINGbrbrThe open living and kitchen area is designed for connection. Relax on the sectional with a cozy blanket and a movie, unwind with a glass of wine, enjoy the record player, or browse the travel books.brbrThe kitchen is thoughtfully equipped for charcuterie, shared meals, and relaxed dinners after tastings. The oversized island seats six and serves as the heart of the home, allowing the cook to stay engaged with the group while preparing meals. A wine fridge, quality glassware, decanter, mixing tools, and additional ice maker are provided.brbrIn warmer months, meals easily extend outdoors to the dining table in the yard.brbrOUTDOOR SPACEbrbrOutdoor living is a highlight of the property. Lounge on the redwood deck under string lights, enjoy a meal outdoors in the yard, challenge your group to bocce, or relax in the hot tub under the stars.brbrThe fully fenced yard includes seasonal fruit trees, lounge seating, and space for dogs to enjoy (pet fee applies). A restored 1930s bar adds character and a unique gathering spot.brbrADDITIONAL DETAILSbrbr• Mini-split system in the primary suite and Nest climate controlbr• Industrial washer and dryerbr• Peloton and free weights located in the primary suitebrbrPlease note: the home is located on a well-traveled road, and some road noise may be audible indoors.brbrLOCATIONbrbrThe home is located directly in Dry Creek Valley, offering easy access to wineries, dining, breweries, cycling routes, river activities, hiking, and the Sonoma Coast. We’re always happy to share local favorites and recommendations.brbrTOT Certificate #1548NbrQuiet hours: 10 PM – 7 AMbrMaximum occupancy: 6 guestsbrMaximum vehicles: 2
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Exceptional(1)

$5301.33

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Private Vacation Home

Luxury Estate | Gatherings | 2 Villas Organic Farm

Healdsburg, California, United States

Summary:brbrUncover a hidden gem on 120 stunning acres, ideal for intimate weddings, celebrations, corporate retreats, board meetings, and family vacations, just minutes from downtown Healdsburg! With two luxurious villas for up to 12 guests, this resort-style sanctuary offers rejuvenation, connection, and warm hospitality. Enjoy organic meals from the garden, wellness activities, and outdoor adventures.brbrbrbrThe Space:brbrThe Best of Both WorldsbrbrbrbrOur two luxury villas offer an immersive stay in nature with comfort and style. Nestled between beautiful pastures and scenic hills, The Estate Villa is a four-bedroom, four-bath estate that combines the luxuries of a high-end resort with the privacy of home. The Barn Villa, a two-bedroom, two-bath modern barn, sits above a one-acre garden and is surrounded by hiking trails and towering Redwoods, blending barn house and tree house charm. brbrbrbrUnique Ranch Experience in Wine CountrybrbrbrbrTravel + Leisure, “50 Best Places to Stay.” The property is private and peaceful yet very conveniently located — only a 10-minute drive to the wonderful restaurants, wineries, and shops in downtown Healdsburg, California. Healdsburg is a top destination in Sonoma County’s wine country, named one of the best places to visit in 2021 by Condé Nast Traveler.brbrbrbrAccommodationsbrbrbrbrThe villas are a luxury oasis with all the comforts of home. Each of the six king bedrooms has a private bath, freshly ironed luxury Frette Italian Linens washed with the ranch's pure water, and premium Avocado organic mattresses. You can fully unwind in the primary bathroom’s freestanding tub or curl up by one of two wood-burning fireplaces. The library is filled with books and games for laid-back evenings by the fire. The home has an automated lighting system and audio/visual is connected throughout the house by Bose Soundtouch.brbrbrbrElevate Your WellnessbrbrbrbrEnjoy our state-of-the-art chef’s kitchens, stocked with farm-fresh produce, and a range of amenities including a 1,200-square-foot fitness center, a private lake, horse stables, an animal sanctuary, gardens, an outdoor glamping tent, a Japanese zen garden, an outdoor Balinese tub, and an outdoor chef’s kitchen with dining area. brbrbrbrYour Perfect ItinerarybrbrbrbrWe’re here to help you with all your celebration plans, from curated dining experiences to unforgettable activities, ensuring your stay is perfect. You may choose from a plethora of experiences right here on the ranch. From arranging Tesla transportation to curating experiences both on and off the ranch, we ensure every detail is handled with precision. Let us take care of the details so you can enjoy quality time with your friends and family! brbrbrbrOne-of-a-Kind Activities, Any Time of YearbrbrbrbrChoose from a plethora of activities right here on the ranch. During warmer months, take a dip in the pool (solar heated May - October) or paddle on our private lake.brbrbrbrFor cooler days, arrange for massages in the picturesque outdoor tent heated via wood burning fireplace, followed by a soak in the clawfoot bathtubs overlooking the breathtaking landscape and grazing wildlife.brbrGuests are also invited to spend time with our dear animal friends who live in the stables on property — goats, a sheep, a pony, and Scottish highland cows.brbrNewTree is a working farm and you are welcome to observe and participate in harvesting the vegetables, planting new seeds, and feeding the animals, as you wish.brbrbrbrBring Your Furry FriendsbrbrbrbrYour pets are always welcome during your stay, as are your horses. The stables are fully equipped to house horses and the property is magnificent for riding.brbrbrbrCulinary DelightsbrbrbrbrA culinary paradise, we have everything you need to create phenomenal meals. Gather freshly-laid eggs from the chicken coop and savor the incredible variety of delicious, organic vegetables grown on property. The newly renovated chef’s kitchen is complete with culinary tools and gourmet cookware, as well as a fully stocked pantry with flavorful spices, pasta, grains, and other dry ingredients. Or if you’d prefer to have someone else cook for you, our private chef crafts exquisite dishes from garden-fresh produce.brbrbrbrHealthy Environment, Healthy YoubrbrbrbrThe entire property is a toxin-free environment. Each indoor space is in an intentional sanctuary with air purifiers throughout and our team only utilizes non-toxic cleaning products to maintain pristine, healing spaces. Additionally, the water is tested regularly, the linens are laundered and ironed onsite, everything grown at the farm is bio-dynamic and all natural, and the skin care products are made from the best quality ingredients. Every aspect of our property, from the soil to the craftsmanship, is biodynamic, regenerative, and sustainable. This commitment allows you to know you’re being taken care of in every possible way.brbrbrbrJoin UsbrbrbrbrWhen you choose NewTree Ranch, you’re standing for something better than a crowded hotel with no real place for your group to privately gather. Instead, you’re immersing yourself in a life of laid-back luxury, where our team anticipates your every need before you even ask for it.brbrbrbrIf you’re ready to experience the breathtaking beauty and exquisite details of NewTree Ranch, we invite you to book your stay today.brbrbrbrbrbrHIGHLIGHTS: brbrbrbr- Personalized pre-trip planning brbr- A dedicated on-site team to manage every detail brbr- Curated ranch experiences brbr- Private chef option brbr- Stocked pantry with delicacies from the garden brbr- Spacious interiors to accommodate large groups with 6+ bedrooms and elevated outdoor spaces with pools, outdoor tubs and showers, and fire pits brbr- Animal sanctuary, horse stables, and guests’ pets welcome brbr- Solar-heated outdoor pool from May to October brbr- Access to indoor gym & fit trail brbr- Tesla transportation for 6 night bookingsbrbrbrbrAS SEEN ON..brbrbrbr• Travel + Leisure, “10 Family-friendly U.S. Ranches to Experience the Great Outdoors”brbrbrbr• Forbes Magazine, Northern California's NewTree Ranch is Redefining luxury.brbrbrbr• Haute Living, “NewTree Ranch: A Place for Revival, Restoration, and Renewal”brbrbrbr• Travel + Leisure, 50 Best Places to Stay.brbrbrbr• Departures, 10 Luxury Experiences for Eliminating Negativity.brbrbrbr• 7 X 7 Magazine, NewTree Ranch: Totally Private Digs Near Healdsburg.
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Exceptional(34)

$356.87

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Private Vacation Home

Morning Dew-A Riverfront Healdsburg Home

Healdsburg, California, United States

Sunny, fun riverfront home in Healdsburg with direct access to Russian River and multiple indoor and outdoor areas to relax and enjoy your time. Great wine country location, less than 10 minutes to Healdsburg's Town Square, and less than 5 minutes to Ru's Farm, or Front Porch Farms. We have multiple decks, a screened porch, a private patio overlooking the river, and everything you need to enjoy them. TOT#3255NbrbrOur calendar is up to date and instant-booking is on.brbrThe spacebrbrMorning Dew is a quaint, 1920s home set under a beautiful old oak tree. In the main house, you'll find a well equipped eat-in kitchen and two separate living spaces where you can curl up by the wood stove with a good book, play cards, watch cable TV or use the WiFi. We have a well stocked kitchen, and provide coffee and tea.brbrThere are several options for sleeping, with a queen bed and a single bed in main house, and a second queen bed in the Love Shack (a rustic studio accessed by a separate entry below the main home). There is a full bath in the main house and a small bath with shower in the Love Shack. brbrThere are many outdoor spaces for relaxing and enjoying the sounds and views of the river. You'll find a shaded deck off the kitchen with a large table for outdoor dining, a small lounge area besides Love Shack, a screened porch part way down to the river, and a shaded platform that sits above the rocky beach.brbrWe have everything you need for a memorable river and wine weekend. Folding chairs, beach towels, and a cooler are available for lounging at the river. Winery maps and recommendations and a picnic basket help you make the most of your winery tour. You'll also find great hiking and road biking in the area, or can arrange a kayaking or canoe trip ending at nearby Memorial Beach.brbrGuest accessbrbrYou will have access to the entire property. We share the path down to the river with our neighbors, but the platform above the river is exclusively ours and there is plenty of room on the rocky beach for everyone to find their own space.brbrInteraction with guestsbrbrWhile we do not live onsite, we are available by phone or electronically for questions and advice. You can talk to me directly via the Ring doorbell anytime.brbrOther things to notebrbrPlease note there are many steep steps down to the river. Use of the stairs and river are at your own risk.brbrWe have a Ring video doorbell.brbrPlease note this is an old and quirky home situated in a rural area. While the oak tree brings lovely shade, it also regularly drops leaves and is home to lots of wildlife. While it varies by season, here are some of the creatures you may come across:brMost likely see - lizards, songbirds, jays, hawks, spiders, caterpillars. brProbably see - deer, ducks, fish, hummingbirds, vultures. brMight see - river otters, quail, snakes, field mice, skunks.brbrOur home is always professionally cleaned between visits, but if seeing a spider in the house could ruin your weekend, it may not be the best choice for you!brbrPlease message with any questions and we hope you enjoy your visit to Sonoma Wine Country!br
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Exceptional(1)

$130.0

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Private Vacation Home

Historic Guest House on Plaza Street

Healdsburg, California, United States

Heartwood Guest House was born in 1880 and reimagined in 2020. As one of the original platted homes of Healdsburg, Heartwood House (and Guest House) are among the oldest buildings in the city—and you can experience a part of this heritage during a long-term stay (30+ days) in wine country!brbrHeartwood Guest House enjoys status as the closest guesthouse to the historic town plaza! This is in-town living at its finest and you will get to experience all that downtown living has to offer: the walkability, the restaurants, the tasting rooms, the shopping, the people, and more. brbrThis space is fully furnished and was refurbished in 2021. Throughout the space you'll notice original 11-ft high ceilings, vintage hardware, and curated artwork that add charm and honor the history of the house. brbrSpecial features of the space include:br- Private entrance through a gated patio space.br- One off-street parking space with additional on-street parking.br- Full-size kitchen in multipurpose room containing a 5-burner gas range + oven, compact refrigerator, microwave, and all cooking/serving utensils. br- Sitting area in multipurpose room with full-size sofa, desk, and Smart television with Hulu LiveTV. br- Bedroom containing a king size bed with Tuft & Needle mattress, electric fireplace, and large storage area.br- Bathroom with restored clawfoot soaking tub and shower enclosure, pedestal sink, and toto washlet toilet. br- In-unit laundry, Mitsubishi mini-split heating/air conditioning, high speed internet, tankless hot water heater. br- Dogs are welcome. brbrbr
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Exceptional(3)

$588.62

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Private Vacation Home

Vinehaven - 3BD Healdsburg Retreat with Spa

Healdsburg, California, United States

Situated just two miles outside of downtown Healdsburg, this home serves as the perfect launch pad for exploring the vineyards of California's famed Dry Creek Valley. This 1600 sq ft retreat is beautifully furnished and decked out in vintage 50s architectural style. The private redwood deck is surrounded by a half-acre of landscaped gardens and boasts a brand-new, six-person Hotspring spa along with endless views of the vineyards and surrounding foothills. A grill and dining areas on the deck and in the garden offer plenty of opportunities for alfresco meals.brbrThe open plan layout, French doors, and beautiful oak flooring gracing this special home and create a spacious feel, with the large living room transitioning into the lovely dining area and a well-equipped kitchen with an island and double oven. Plantation shutters, crown molding, and recessed lighting add even more period charm.brbrThe romantic primary suite with garden and vineyard views is furnished with an oak sleigh with luscious linens. The en suite bathroom features a dark blue claw-foot tub and shower, as well as new, granite-topped vanity. The second and third bedrooms share a second bathroom with a large tiled walk-in shower and pedestal sink. A queen size sleeper sofa in the living room offers additional guests an extra bed.brbrEntertainment options include a 50-inch 4K ultra smart TV, Comcast cable, a DVD player, and high-speed WiFi with up to 600 mbps download speed!brbrThings to Knowbrbr• Check-in time: 4:00 p.m.br• Check-out time: 10:00 a.m.br• Quiet hours are from 9 p.m. to 7 a.m.br• No smoking is permitted anywhere on the premises.brbr• 2 dogs welcome in this home. No other animals are allowed without specific Beaux Maison approval.br• Parking notes: There is free parking available for 3 vehicles.br• Guest entry instructions: This rental utilizes an E-lock, a digital lock that requires a unique code to enter. This code is reset after each guest's stay.brbrLIC24-0042brTOT# 1685NbrbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrYou must be 25 years or older to rent this property.
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Exceptional(15)

$900.38

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Private Vacation Home

Tranquil Healdsburg Escape | Near Wineries & Plaza

Healdsburg, California, United States

The spacebrStaying with Away2Vacay you will find yourself in the heart of wine country with rolling hills of grapevines and green pastures when you make your way to Healdsburg. With lush gardens and a secluded feel, Maison Cachée will welcome you with a peaceful ambiance that will spoil each lucky guest in no time. And, when you want to venture out a bit, a plethora of shops, restaurants, and grocery stores are mere minutes from your front door in downtown Healdsburg. Oenophiles will love one extra-special perk at this home - when making reservations, guests can receive various discounts and savings at several local wineries like Ridge, Wilson, Mazzocco, Matrix, and Rock Pile. Further details regarding the perks will be provided at the time of your booking confirmation.brbrWhen everyone returns from various adventures, the interior has two wonderfully furnished living areas to gather in and a well-equipped kitchen just waiting to assist with preparing tasty homecooked meals. The accommodating dining table will be great for formal meals inside, yet the summer breeze will be calling your name for alfresco dining on the furnished deck. When you want to keep things casual, fire up the gas grill and throw on some burgers and dogs as the sun dips behind the treetops.brbrThis special retreat is just waiting to create unforgettable memories, so make your way to this Northern California gem today!brbrThe home has 2 twin size roller beds located in the master bedroom closet. Sheets and comforters are located in the upstairs hallway closet.brbrOther things to notebrNetflix, Hulu, Disney+, HBO, etc. streaming are available (guests need their own account).brbr2 dog(s) are welcome in this home for a $150 pet fee. No other animals are allowed without specific approval.brbrParking notes: There is free parking for 4 vehicles. Parking is located in the driveway.brbrSecurity camera details: There is a ring doorbell on the front door.brbr***The indoor fireplace is out of service and should not be used***brbrOur property is set in the countryside in the beautiful Dry Creek Valley. It's not unusual to come across bugs, spiders, ants, etc. Our home is treated by a pest control company on a monthly basis as a deterrent.brbrCounty permit number: TVR22-0027brbrCounty tax number: 4272N
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$2705.58

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Private Vacation Home

Riverstone Estate sleeps 12 Pool Bocce Spa

Healdsburg, California, United States

Riverstone Estate is a private, Wine Country retreat located just minutes from downtown Healdsburg in Sonoma County. Set on a gated Russian River–side property, this historic estate offers more than 5,300 square feet of living space, three separate homes, eight bedrooms, and nine-and-a-half bathrooms, making it an exceptional destination for extended family gatherings, wedding groups, multi-generational vacations, and Wine Country adventures with friends. The estate accommodates up to 12 guests to select any combination of five bedrooms, each featuring its own private bathroom for comfort and privacy.brbrDesigned as a family compound, Riverstone Estate blends vintage Wine Country elegance with modern amenities. The property includes a seasonal in-ground pool, solar-heated from May through September, along with a year-round hot tub, fire pit, bocce ball court, horseshoe pit, basketball hoop, badminton/volleyball lawn, ping pong table, frisbee golf area, and a fully equipped exercise room. These resort-style features create a private, immersive experience comparable to a boutique resort—yet exclusively reserved for your group.brbrThe estate consists of three distinct homes thoughtfully arranged around beautifully landscaped grounds filled with gardens brimming with flowers and vegetables, fountains, mature trees, and peaceful seating areas:brbrQueen Anne House (3BR/4BA): This is the largest residence, featuring a gourmet kitchen with island, granite counters, and high-end appliances. Guests enjoy a formal dining room, a classic living room with hardwood floors, and an outdoor patio with grill and firepit for al fresco dining.brbrThe Coop (2BR/2BA): A cozy and comfortable cottage with two queen bedrooms, two full baths, a kitchenette, and a small living area—ideal for couples or guests seeking a quiet retreat within the estate.brbrOak Tree House (3BR/3BA): This home provides a full kitchen, living room, and multiple outdoor seating areas, including a deck and small terrace. The primary suite has an ADA-compliant bathroom and ramp access, offering accessibility for guests who appreciate or require it.brbrRiverstone Estate is known for its serene setting, Russian River views (no water access), and beautiful brick patios with outdoor seating. Guests enjoy cable ready high-speed WiFi, multiple kitchens, and spaces designed for gathering, cooking, celebrating, and relaxing. Wildlife, stargazing, and quiet natural moments are common throughout the stay.brbrLess than two miles from Healdsburg Plaza, the estate offers fast access to world-class wineries, farm-to-table dining, boutique shopping, cycling routes, and outdoor activities throughout Alexander Valley, Dry Creek Valley, and the Russian River Valley. Its proximity and privacy make it a rare find for travelers seeking an elevated Wine Country vacation.brbrRiverstone Estate is frequently chosen for wedding groups, milestone celebrations, extended family trips, and wine-focused getaways due to its size, flexibility, amenities, and unmatched privacy. Guests value the feeling of having an entire private resort to themselves, with activities and comforts for every age group.brbrPermit ZPE12-0027. Minimum age to reserve: 33.
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Exceptional(19)

$1012.47

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Cottage

Heart of Healdsburg Cottage for 4, Pool, Spa, Fire Pit, WIFI, BBQ

Healdsburg, California, United States

The Heart of Healdsburg Cottage is a one acre property with an in ground pool, hot tub, hobby vineyard, and walking distance to wineries and the downtown plaza square. Because it is close in, the road is busy (access to the Russian River communities via Westside Road), however the back yard space creates a nice buffer from the traffic. The outdoor seating area offers lounges at poolside and a beautiful picnic table under the fairy lights strung above in the walnut tree. A large deck and hot tub sits outside the French doors entering the kitchen and a beautiful glass fire pit just beyond the deck.brbrThis lovely little cottage is really a unique and hard to find category for a few guests or 2 couples. Two bedrooms each have a queen bed with comforters, and robes are provided for each guest. A fireplace insert creates ambiance in the evenings, and a large modern kitchen stands ready for even the most discerning of chefs.brbrWestside Road is a popular bicycle route with a loop through the Dry Creek Valley, where in season you may stop at one of several farms available to visit and dozens of wineries waiting to host you for a tasting. Walk to downtown, less than one mile from the house, for shopping, gourmet treats and world class restaurants, tasting rooms and breweries. True West Film Center offers first run films and studies in the classics, and the galleries in town present many artists and their interpretations of our beautiful wine country.brbrThis beautiful cottage is ready for you to create new memories!brbrLIC24-0365brbrPlease note: When booking this home, an additional contract will be sent to you and must be signed to confirm your stay with us.
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Exceptional(26)

$1163.52

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Private Vacation Home

WC Oasis with Hot Tub - Wine Tastings Included

Healdsburg, California, United States

Tucked just eight minutes from downtown Healdsburg, this Luxurious Wine Country retreat invites you to slow down, reconnect, and savor the best of Sonoma County. Wake to peaceful vineyard views, spend sun-filled days exploring nearby wineries, and return home to evenings spent soaking in the hot tub, gathering around the fire pit, or laughing over games long into the night.brbrThoughtfully remodeled and designed for togetherness, this open-concept estate includes a main house and a separate guest house, comfortably accommodating families and groups while offering space and privacy for everyone. With indoor and outdoor living flowing seamlessly, the home is as perfect for relaxed mornings as it is for memorable celebrations.brbrWalk to renowned wineries like Mauritson and Ridge, or take a short drive into Healdsburg Plaza for world-class dining, tasting rooms, and boutique shopping. Whether you’re here for wine tasting, family time, or a special occasion, this property offers an authentic and elevated Wine Country experience.brbrMain Housebr• Open-concept living with a cozy indoor fireplacebr• Folding glass doors opening to a large entertainment deckbr• Fully equipped kitchen with large island and modern appliancesbr• King bedroom on the main levelbr• Two queen bedrooms upstairsbr• Two full bathroomsbrbrSeparate Guest Housebr• Private king bedroom upstairsbr• Downstairs lounge with an Article memory foam pull-out sofabr• Full kitchen with bar seatingbr• Two full bathroomsbr• Dedicated workspace, ideal for remote workbrbrOutdoor Living and Entertainmentbr• Private hot tubbr• Propane fire pit for evening gatheringsbr• Bocce court and cornhole for friendly competitionbr• Hammock for quiet afternoonsbr• Back deck with dining table, couch and gas BBQbrbrGame Room and Extrasbr• Large TV with comfortable seatingbr• Ping pong table and dart boardbr• Two multi-game arcade unitsbr• Game table with board games and puzzlesbr• Compact workout area with treadmillbr• Washer and dryer for guest usebrbrFamily Friendly Amenitiesbr• Portable cribbr• High chairbrbrGuest Access and PrivacybrGuests enjoy exclusive, private access to the entire property, including the main house, guest house, game room, and all outdoor spaces. Your privacy is respected at all times, while responsive support is available via phone or message whenever needed.brbrLocal Winery Partnerships Complimentary TastingsbrAs our guest, enjoy complimentary wine tastings at three small, locally owned wineries. The guest of record must be present for all tastings.brbr• Croix Estate Winery featuring exceptional Pinot Noir and Chardonnaybr• Merriam Vineyards crafting Old World inspired Bordeaux style winesbr• Orsi Family Vineyards specializing in expressive Italian varietalsbrbrImportant Notesbrbr• The creek on the property is seasonal and may be dry depending on the time of yearbr• A standard rental agreement will be sent after booking confirmationbr• Smart Lock located on main house front door allowing for contactless check inbrbrAlongside a beautifully maintained home, our thoughtful hospitality and responsive communication ensure a smooth, relaxing stay from arrival through departure.brbrTOT 1089N | PERMIT TVR21 0126 | LICENSE LIC23 0093
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Exceptional(4)

$330.72

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Private Vacation Home

Heavenly Hideaway - Wine Tastings Included

Healdsburg, California, United States

Just 2 Blocks from Healdsburg Plaza – Step into Wine Country elegance at Heavenly Hideaway, a thoughtfully remodeled historic home that puts you at the heart of Healdsburg's culinary and wine scene. Walk to award-winning restaurants, boutique shopping, and premier tasting rooms, then retreat to your private sanctuary for relaxation and connection.brBeautifully renovated in 2015, this sophisticated home blends modern luxury with Wine Country charm, featuring an open-concept chef's kitchen, high-end finishes, and inviting living spaces perfect for extended stays, relocation, remote work, or savoring Wine Country at a slower pace.brbrThe SpacebrBedrooms & Sleeping:brPrimary Suite – Luxurious master bedroom with en suite bathroom and premium beddingbrAdditional Bedrooms – Comfortable guest rooms with high-quality linens and thoughtful detailsbrbrLiving Areas:brOpen-Concept Layout – Seamless flow between kitchen, dining, and living spacesbrChef's Kitchen – Stainless steel appliances, sleek countertops, ample storage, and large island perfect for cooking and gatheringbrIndoor Gas Fireplace – Cozy ambiance for relaxing eveningsbrContemporary Furnishings – Stylish, comfortable pieces throughoutbrDedicated Workspace – Ideal for remote work with high-speed WiFibrbrOutdoor Spaces:brPrivate Backyard – Perfect for morning coffee or evening winebrBBQ Grill – Gas grill for outdoor cooking and entertainingbrOutdoor Seating – Comfortable areas for al fresco diningbrbrModern Amenities:brHigh-speed WiFi throughoutbrDrip coffee makerbrFull kitchen with modern appliancesbrIn-unit washer and dryerbrCentral heating and air conditioningbrSmart TV with streaming capabilitiesbrContactless check-in for conveniencebrbrBeyond the beautiful home, it's the hospitality that makes the difference. Our guests consistently highlight our attentive, thoughtful service and how we go above and beyond to ensure each stay is seamless. While we offer contactless check-in for your convenience, you'll feel warmly welcomed and genuinely cared for by hosts who know and love Healdsburg as much as we love sharing it with you.brbrExclusive Wine Country PerksbrbrAs a WC Lodging guest, enjoy free tastings for up to 6 guests at three exceptional local wineries:brCroix Estate Winery – Boutique producer celebrated for exceptional Pinot Noir and Chardonnay ($45 value per person)brMerriam Vineyards – Family-owned estate crafting elegant, Old World-inspired Bordeaux-style wines ($35 value per person)brOrsi Family Vineyards – Locally loved winery specializing in expressive, small-lot Italian varietals like Sangiovese and Schioppettino ($35 value per person)brbrGuest of record must be present for all tastings. An unforgettable way to toast your Wine Country getaway.brbrPrime LocationbrbrWalking Distance to Everything:br2 blocks to Healdsburg PlazabrSteps from award-winning restaurants including SingleThread, Valette, and BravasbrWorld-class wine tasting rooms at your doorstepbrBoutique shopping and art galleriesbrFarmers market and local eventsbrbrNearby Attractions:brRussian River Valley wineries (5-15 minutes)brDry Creek Valley wine country (15 minutes)brAlexander Valley vineyards (20 minutes)brArmstrong Redwoods State Natural Reserve (20 minutes)brRiver Beach and Lake Sonoma recreationbrbrbrPerfect For Extended Stays:brRemote Work & Digital Nomads – Live where others vacation, with dedicated workspace and high-speed WiFibrCorporate Relocations – Temporary housing during job transitions or extended business assignmentsbrSeasonal Stays – Experience Wine Country through harvest season, spring bloom, or winter tranquilitybrTravel Nurses & Professionals – Comfortable home base near healthcare facilities and workplacesbrHome Renovation Guests – Upscale accommodations while your home is being remodeledbrExtended Family Visits – Comfortable setting for longer visits with loved ones in the areabrWine Industry Professionals – Ideal for those working harvest or extended wine country projectsbrbrbrHouse Rules & Policies:brPet-Friendly: Small dogs welcome (pet fee applies, please inquire)brCheck-in: Contactless, seamless arrival processbrParking: Private driveway fits 1 car in addition to ample street parkingbrQuiet Hours: Respectful of residential neighborhoodbrBooking subject to property manager's rental agreement (excludes Airbnb bookings)brbrHeavenly Hideaway offers the rare combination of prime downtown location, thoughtful design, and genuine hospitality that transforms an extended stay into a true home away from home. Whether you're here for work, relocation, or simply to immerse yourself in Wine Country living, we're committed to making every day of your stay exceptional.brYour downtown Healdsburg home awaits.
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$1308.0

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Agritourism

Modern Vineyard Farmhouse - Close to Downtown Healdsburg - 4 BD/4 Ensuite Baths

Healdsburg, California, United States

What could be more memorable than a holiday gathering with family or friends in the Wine Country Our beautiful vineyard home has not been available to rent for more than two years. But it is for this holiday season! The Farmhouse can accommodate four couples, each with their own ensuite, full-sized bathroom.brbrMore than a Vacation Rental or a Hotel, this registered Farm Stay juxtaposes the modern Wine Country experience with Sonoma County’s viticulture heritage in a contemporary, luxurious interior. Nestled in the heart of Dry Creek Valley among Healdsburg’s well-known wineries, the Modern Vineyard Farmhouse offers accommodations for up to 8 guests. Guests are enveloped in a working viticultural property that is an easy, paved drive of less than a mile to Healdsburg’s downtown restaurants, shops and spas. Ideal for cyclists, the Modern Vineyard Farmhouse is centrally located about 1/2 mile from the intersection of West Dry Creek Road and Westside Road, two beautiful and well-know cycle routes.brbrThis 2,800 square foot home was recently renovated from top to bottom to create an updated interior with a modern aesthetic. Decorated in a sophisticated style with playful touches, the carefully selected interior pieces create a unique, comfortable and fun interior. The Living Room and Dining Room share an elegant yet cozy fireplace. Those who are musical may enjoy the Baby Grand Piano in the Living Room. For movie watching, the Media Room’s 60-inch flat screen TV and mega-sofa offer a comfortable hangout space. The Modern Vineyard Farmhouse has four light-filled Bedrooms – each with vineyard views, a flat screen TV and a private, beautifully renovated Bathroom. brbrThe Modern Vineyard Farmhouse has a newly built Chef’s Kitchen that opens onto the vineyard-facing deck for a classic Wine Country indoor-outdoor dining experience. For those who like to cook, the kitchen is fully equipped with all that is needed to create and serve inspired meals, including a Viking 6-burner stove. Big John’s Market, a favorite local grocery store, is an easy three minute drive, as is Safeway and the Healdsburg Farmer’s Market in the summer months.brbrThere is a private WiFi connection. Proprietress lives on the property and will make sure you have everything you need for an unforgettable experience.brbrbr
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$172.0

/ Nightly
Private Vacation Home

Dragon Cottage | Historic house in Healdsburg with Russian River Valley views

Healdsburg, California, United States

Dragon CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled on the side of Fitch Mountain you'll find the Dragon Cottage! Boasting sweeping views of the Russian River, lush vineyards, rolling hills, and the mountain itself - there is never not something to look at. When you can pull yourself away from the home's breathtaking views and impressive interior, head for Camp Rose, a semi-private beach access point on the Russian River, or to the public Del Rio Woods Beach. Located in wine country, you can't miss out on the fabulous wine-tasting opportunities around you! Dry Creek Vineyard and Kendall-Jackson Wine Estate & Gardens are both less than 12 miles away.brbrAs one of the original Camp Rose homes, this historic charmer was originally built in the 40s. Its unique charm can be noticed through the small details like warm wood flooring, built-ins, and crown molding. Sit back and enjoy the comfort of the living room's ample seating and lovely views, or head for the rooftop deck where you can be one amongst the trees. Steps away, the home's full kitchen exudes a sense of retro charm with its checkered flooring. When mealtime rolls around, dine with your loved ones at the quaint breakfast table or at the expansive formal dining table.brbrPeaceful slumber and sweet dreams will come naturally in the home's five bedrooms. Keeping you cool and comfortable no matter the season, each room is embraced with a cool blast from the central air-conditioning. A private washer/dryer and board games round out the cottage's interior perks. brbrOutside, play a game of Ping-Pong under the California sun while the kids enjoy the playset. As the sun begins to set over the Russian River Valley, head for the bubbling warmth of the hot tub.brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by Vacasa's good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 2 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
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$131.0

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Private Vacation Home

Rooster Cottage | House with Russian River views, hot tub, back deck, W/D, patio

Healdsburg, California, United States

Rooster CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to the peaceful home away from home that will have you relaxing in style! This gorgeous home was built in the 40s-50s and is part of the historic Camp Rose neighborhood and is nestled on the side of Fitch Mountain. There is a semi-private Russian River beach access called Camp Rose that is a half-mile walk down from here - it is only for people in the Camp Rose community! There is also a public beach access called Del Rio Woods, which is about a mile up the road. Downtown Healdsburg is a short two-mile drive away where you will find restaurants, parks, and endless vineyards and wineries! Some must-visit attractions include Dry Creek Vineyard, Trentadue Winery, Kendall-Jackson Wine Estate & Gardens, Luther Burbank Center For The Arts, Safari West, and Armstrong Redwoods State Natural Reserve.brbrThis beautiful retreat offers stunning views of the Russian River, vineyards, rolling hills, Fitch Mountain itself, and the birds that love to perch and soar overhead. Outside, the extensive back deck enjoys a hot tub for soaking and relaxing while taking in the views of the Russian River Valley. The deck also offers a convenient outdoor dining area, a sitting area with plenty of comfortable furniture, and a hanging egg chair.brbrInside, this beautiful home away from home enjoys a sunny living area where you all can gather and plan your next adventures, a well-appointed kitchen with all the essentials and a Nespresso coffee maker, a sunny dining room with gorgeous views, and an attached laundry room with a washer/dryer.brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by Vacasa's good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
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$485.86

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Agritourism

Charming Alexander Valley Farmhouse with loft, hot tub & a complementary tasting

Healdsburg, California, United States

Starlite Vineyards EscapebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience the perfect blend of rustic charm and modern comfort at Starlite Vineyards, a stunning property located in the heart of Geyserville, CA. Nestled within the breathtaking vineyards of Alexander Valley, this enchanting retreat invites you to unwind in a beautifully restored 1912 farmhouse. With exclusive perks right on the grounds of the acclaimed Starlite Vineyards, your stay promises to be both relaxing and memorable.brbrStep inside to discover timeless elegance, featuring hardwood floors, crown moldings, and built-in cabinetry that seamlessly blend historic charm with modern amenities. The updated kitchen opens to a cozy family room, while formal living and dining areas provide inviting spaces for gatherings. With three spacious king-sized bedrooms and two full bathrooms, including a primary suite, this home is perfect for families or groups seeking comfort and convenience.brbrOutside, indulge in the serene beauty of the surrounding vineyards. Start your day with coffee on the deck, soak in the private hot tub, or explore the lush gardens. Your stay includes a complimentary wine tasting at the adjacent barn-turned-tasting room, where you can savor award-winning, boutique wines crafted from the unique terroir of the region.brbrAs part of a working vineyard, immerse yourself in the authentic rhythm of Wine Country. Depending on the season, you may witness the charming sight of vineyard workers tending to the vines. With ample amenities, including a gas grill, central AC, and internet access, Starlite Vineyards offers everything you need for a delightful getaway. Book your stay today and embrace the beauty and flavor of Alexander Valley!brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 4 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
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