Vacation Rentals By Owner In Westport, CT

$608.55

Main Street Westport, walk to shops, dining, downtown

Westport, Connecticut, United States

Looking for a great deal Discounts are automatically applied based on your length of stay! No need for promo codes or requests. The total price you see includes your savings, so you can book with confidence. Discounts may display differently across booking platforms, but rest assured, they’re built into your final price.brbrWelcome to The Main Street Stay in charming Westport, CT! brbr brbrExperience the timeless charm of small-town bliss in this spacious Westport retreat. brbr brbrPerched above Main Steet, this PRIVATE gem offers modern comforts and serene charm just a short stroll from boutique shopping, local dining and vibrant attractions. With its perfect blend of location and convenience, it’s the ideal getaway for creating lasting memories. brbr------------------------- brbrTHE SPACE (occupancy 8) brbrMain Level: Living room, kitchen, dining room and three bedrooms on main level (stairs required) brbrDiscover four fully furnished sleeping quarters for rest and rejuvenation. Spacious and tastefully adorned, these rooms cater to your comfort and individual style. Whether seeking peaceful slumber or personal retreat, these bedrooms fulfill your every need. brbrPrimary Bedroom en Suite: Queen sized bed, dresser, 2 closets, private bathroom with bathtub/shower, and lots of natural light. brbrSecond Bedroom: Queen sized bed, dresser and closet brbrThird Bedroom: Queen sized bed, dresser and closet brbrLiving Room: At the heart of the home, the living room radiates warmth and hospitality. With comfortable seating and abundant natural light, it's perfect for quiet evenings or gatherings with loved ones. brbrKitchen: Fully equipped for culinary adventures including electric stove/oven, microwave, air fryer, dishwasher, Keurig Coffee Maker and so much more. Stocked with pantry essentials. brbrCharcoal Grill: Situated on porch located off kitchen. brbrBathrooms: Three meticulously designed bathrooms. Crafted with attention to detail, they blend practicality with luxury, modern fixtures, and ample storage. Perfect for quick showers or leisurely soaks, these bathrooms offer the ideal relaxing ambiance. All bathrooms offer complimentary shampoo, conditioner, body wash. brbr brbrLower Level: brbrThe lower level has a versatile living space designed for both productivity and relaxation. brbrDedicated Office Area: Two desks and chairs, perfect for remote work or study. brbrFourth Bedroom: Private, separated from living space by French doors, with full bath and laundry area brbrBathroom: Full bath with shower/tub tucked away in the lower level fourth bedroom brbrLaundry: A full-sized washer and dryer are in the fourth (lower level) bedroom. brbrLiving space: This space is equipped with a cozy couch, additional chairs, a foosball table, and a keyboard, making it a great spot for kids to unwind separately from the rest of the family. brbrWhether you are working remotely or just looking for a peaceful retreat, this space offers the perfect balance of functionality and comfort. brbr brbrMODERN AMENITIES: brbrHigh-speed internet for connectivity brbrFull-sized washer and dryer in lower level bedroom brbrOutdoor Patio/BBQ Grill offers relaxation and recreation opportunities brbrLarge two-car garage available for guest use brbrHigh Chair available brbrBath amenities left to get you started (toilet paper, shampoo, conditioner and body wash) brbr brbrGUEST ACCESS brbrYou'll have exclusive access to the entire property during your stay. From the 4 bedrooms and 3 bathrooms to the cozy living room, every corner of this well-appointed space is at your disposal. Feel free to make yourself at home and enjoy all the amenities and comforts this property offers. It's your private sanctuary where you can relax, unwind, and create wonderful memories throughout your stay. brbr brbrPET MUST BE APPROVED PRIOR TO BOOKING brbrWe love furry friends, but all pets must be approved before booking. Pets are not allowed on furniture, must be crated if left alone, and you are responsible for cleaning up after them. A pet fee of $20 per pet, per day applies and may be added to your reservation after booking. brbr brbrOther things to note brbrThe starter pack will help you get started with your stay and includes one Paper towel, dishwasher pods, dish soap, and a few garbage bags, as well as shampoo, conditioner, and body wash. brbrFor your safety, a security camera are installed at the front door and the front driveway of the property to monitor the exterior for the safety and security of our guests and the premises. There are no cameras or listening devices inside the property. brbrThe camera will be active throughout your stay and is positioned solely for external monitoring and will not compromise your privacy within the accommodation. brbrIt is worth mentioning that the property is situated on a main road, but sits up off of the street. We do want guests to be aware that they will have to back out of the driveway, but can use the neighbors driveway to back out safely. brbr brbrWe can't wait to host you!brbrNOTE Before Booking: brbrFAMILY RENTAL ONLY brbrWe require at least one party member to be 25 (twenty-five) years of age! brbrGUEST IDENTIFICATION REQUIRED brbrGuests may be asked to complete a Clear ID verification before check-in. If this is not completed, the entry code will not be provided, and the reservation will be subject to cancellation with no refund. brbrFALSIFIED RESERVATION brbrAny reservation obtained under false pretense will be subject to forfeiture of the reservation deposit, damage deposit, and/or balance of rental payment. NO PARTIES, EVENTS, PERFORMING ARTISTS OR BANDS ARE ALLOWED AT ANY TIME. The maximum number of guests or visitors for this house, as indicated in the listing, should be honored at all times, day or night. These are cause for eviction with no refund and may damage our ability to offer the home to future guests, exposing you to liability. This is a quiet residential neighborhood; please be respectful of the neighbors at all times!

4

Bed

3

Bath

8

Sleeps

$498.33

/ Nightly

Private Vacation Home

Charming 2-Bedroom House 1 Mile To The Beach,Deck, Wifi & Game Room

Westport, Connecticut, United States

Modern 2BR, 2.5BA home in Westport, just 1 mile from Compo Beach! Sleeps 6 with a finished basement game room and pull-out couch. Enjoy high-speed WiFi, a spacious deck, grill, and hammock—perfect for relaxing. Centrally located near dining, shopping, train and all Westport attractions including Sherwood Island State Park. Stylish, comfortable, and family-friendly!brPeaceful, private home in Westport, CT—perfect for families or close friends. Centrally located to all that Westport has to offer. brbrThe home features 2 comfortable bedrooms (1 king, 1 queen) Bathrooms are newly renovated with walk-in showers and modern finishes. Enjoy a fully equipped kitchen, sunlit dining areas, and cozy living spaces.brbrLocated minutes from Compo Beach, Levitt Pavillion, Sherwood Island State Park , farmers markets, shops and restaurants. There are several grocery stores minutes away including Whole Foods, Trader Joes', The Big Y and Stop n Shop.

2

Bed

2

Bath

6

Sleeps

$2127.5

/ Nightly

Private Vacation Home

Summer, FURNISHED: CENTRAL WESTPORT ESTATE, 60' pool: 2 mins to beach/town/train

Westport, Connecticut, United States

Summer rental of the most private and central multi-acre estate in Westport, CT - available June-August! Fully furnished. brEscape to serene, woods-enclosed tranquility. Hit Compo Beach (access included) or Main Street dining/downtown shopping, both in two minutes. I-95 and train four minutes away. Walk your dogs on your estate or a land preserve just outside your gate, at the end of a private cul-de-sac abutting four of the grandest homes in the northeast. This fully furnished 7-bedroom home in Westport easily sleeps ten and offers recreational amenities on par with a top resort: Your bedrooms are steps away from one of the largest swimming pools in the state - your own 60 foot decoratively tiled and laned pool, gazebo seating 10+ w/ teak furnishings, cabana w/teak bar, enclosed private changing areas and 1.5 baths poolside. Your home offers a fitness room w/Universal, Power Plate and streaming HD Amazon music. Privately entertain guests from your extensive private grounds, w/outdoor grill and professional kitchen. Professional caretaker available on-site 4 days per week (as owner lives two doors away on an abutting 6+acre property). Fiber-optic 500mb internet/whole home Wi-Fi. Experience sophisticated Westport living during your summer of a lifetime!

7

Bed

5

Bath

14

Sleeps

$2012.5

/ Nightly

Private Vacation Home

Westport Summer retreat w/ 40 Ft saltwater pool, 6 bedrooms + guest cottage

Westport, Connecticut, United States

A Westport summer vacation retreat. The property features a recently built 40 foot saltwater gunite heated pool and spa and separate guest cottage. The expansive outdoor patio and deck includes 3 separate seating areas with an upper deck, lower covered deck and bluestone patio with an outdoor TV, firepit table and heat lamp-- perfect for summer gatherings. The lower level features a recreation room and gym with a second refrigerator/freezer, wine cellar and full bathroom. The front porch is perfect to view the sunset over cocktails. The expansive square footage is well utilized with 9+ high ceilings and a great room living space, separate den, 2 home offices, and a downstairs guest bedroom suite/full bath, with 5 additional bedrooms upstairs. The guest cottage makes 7 bedrooms, and includes a full kitchen, washer/dryer and full bath. Beach pass available. Availability: June-Labor Day. One month minimum.

7

Bed

6

Bath

14

Sleeps

$2111.07

/ Nightly

Private Vacation Home

Westport Family Friendly Oasis

Westport, Connecticut, United States

Be prepared to be wowed! Westport home close to beach. If you are looking for that special place to call Home, this is the house for you. Large windows throughout offer light and warmth, highlighted by designer light fixtures and custom finishes. Finished on 3 floors, this house offers space for all including all ensuite bedrooms, gourmet kitchen and recently updated primary bath. Great neighborhood, quiet, walk to town, close to beach and easy commute to train station. Large private and flat back yard with patio directly accessible via the sunroom is perfect for savoring the outdoors.

Bed

Bath

Sleeps

$213.9

/ Nightly

Apartment

Studio Flat Above Historic Cider Mill

Westport, Connecticut, United States

Escape to a unique waterfront studio in a restored 19th-century Cider Mill on the Westport/Southport border. This sunlit retreat offers stunning views of Sasco Brook, exposed beams, and modern comforts. Perfect for couples or solo travelers, it comfortably sleeps 2-3 and includes a dedicated workspace with high-speed Wi-Fi. A truly historic and peaceful getaway.brbrThe Space:brThis sunlit waterfront studio is perched atop a restored 19th-century Cider Mill, blending timeless character with modern comfort. The dramatic A-frame ceiling, original exposed wood beams, and hardwood floors create a bright, airy, and historic atmosphere. The open-plan layout is thoughtfully designed for your comfort and convenience:brbr* Sleeping Area: A comfortable queen-size bed. An air mattress is also available to accommodate a third guest.br* Living Space: A cozy couch, large-screen smart TV with cable and an Amazon Fire Stick, and an Amazon Alexa/Sonos sound system.br* Kitchen & Dining: A full kitchen equipped with a microwave, toaster, coffee maker, and all necessary plates, glasses, and utensils. The dining table seats four.br* Dedicated Workspace: A desk with high-speed Wi-Fi and an Ethernet connection provides a perfect remote office setup.brbrThis retreat is ideal for history lovers and design enthusiasts. We are pet-friendly and can provide a crib, pack `n play, or high chair upon request.brbrAccess:brGuests will have private and exclusive access to the entire studio apartment. Check-in is seamless with our self-check-in process via a secure lockbox. Luggage drop-off is allowed for your convenience.brbrYour stay also includes access to:br* One dedicated parking spot in the private lot.br* A shared washer and dryer located within the building.br* A shared outdoor seating area by the water.br* 24/7 access to B@Work, a multi-level co-working space with waterfall views, located downstairs in the same building.brbrDetails to Note:brTo ensure you have a wonderful stay, please keep the following details in mind:brbr* Historic Building: This studio is part of a beautifully restored mid-1800s Mill. As a result of its historic charm, the bathroom is compact but fully functional and cozy.br* Stair Access Only: The apartment is located on the second floor and is accessible via one flight of stairs. There is no elevator in the building.br* Potential for Noise: We are located on a main road (Post Road), which can be busy. While many guests describe the environment as peaceful, we want to be transparent about the potential for some traffic noise.br* Long-Term Stays: We welcome long-term stays. Please inquire for more details.brThe most important House Rule is, respect our neighbors and community. Mystic is a quaint, coastal New England town. As hosts, and guests, we share in the responsibility of keeping Mystic a great place to visit, and to LIVE. Honor the noise ordinance. Be the guest that you would want staying in a vacation rental near your home.brbrIf you park on Church Street, please do not block our neighbor`s driveway.brbrIf you have chosen our home for a special occasion and plan on having a gathering with family & friends. Please respect our neighbors and our house. Our maximum guest policy is 7 adults. As a matter of local health, safety & parking guidelines, any prolonged gathering of more than 7 adults is prohibited unless approved PRIOR to booking. If you plan on being outdoors you must reduce volume. Respect our neighbor`s right to Quiet Enjoyment.brWe do allow small gatherings, however, we expect our guests to be respectful of our neighbors. Please be mindful of the volume and timing of any events or gatherings. More importantly, enjoy yourselves and allow our neighbors to enjoy their time as well. brbrThere is absolutely NO smoking inside the house.brbrWhile we welcome pets at all of our properties, we expect this amenity to be used responsibly. Please do NOT allow pets on furniture, especially beds. Also, do not allow pets to soil or stain carpets or floors.brbrFireplaces are NOT functional. They are for aesthetics and must not be used.

1

Bed

1

Bath

3

Sleeps

$384.1

/ Nightly

Private Vacation Home

Summer rental House Westport

Westport, Connecticut, United States

Stunning three bedroom house with Dining Room, Living Roomon on a private road, one mile from beach, near town center, one hour by train to New York's Grand Central Station.brbrThe property is located 1 mile from local restaurants and shopping areas and close to Nature Center.brbrThe property requires a 30 day minimum stay and up to 90 days maximum. brbrPlease contact the Partner for more details on the property.

Bed

Bath

Sleeps

$1518.0

/ Nightly

Private Vacation Home

Luxury Coastal Estate, 7min to NYC train & beach. Heated pool & amazing gardens

Westport, Connecticut, United States

This beautiful centrally located 7,000 sf luxury coastal colonial farmhouse sits on 2+ acres in property with expansive private gardens and only few mins away from beaches, the train to NYC and downtown Westport. Fresh vegetables & chicken eggs available from the gardens to our guests. One would never feel the need to leave with all the activities on the property such as heated pool/spa, fire pit, badminton, ping-pong, trampoline, basketball, movie theater, arcade, home gym and chef kitchen and outdoor kitchen with grill. The 8 bedrooms include 1 king, 3 queens, 1 trundle daybed, 1 bunk bed, 3 twins, and 1crib. However if you are feeling adventurous there is an amazing downtown with many stores and restaurants. Kayaking, hiking, fishing, ice skating, tennis, golf course all 5-10 mins away. And it’s only an hour to NYC where we regularly go for the day or to the ski slopes.br

9

Bed

8

Bath

15

Sleeps

$426.32

/ Nightly

Private Vacation Home

Boho Chic Private Home in the Heart of Westport CT

Westport, Connecticut, United States

The best of both worlds! Centrally located Westport flat surrounded by greenery and wildlife, tucked in a private neighborhood.. Minutes from Compo Beach, Sherwood Island State Park, Downtown Westport, Downtown Saugatuck, Long Shore Golf Course, Nyala Farms, and the Westport Train Station. The perfect place to experience everything Westport has to offer, with the ability to unwind in a relaxing and secluded space. Awesome Westport flat minutes from the beach, golf courses, downtown Westport, Saugatuck River, Sherwood Island State Park, Nyala Farms, the train station and more!!brbrNewly renovated 2 bed/1 bath fully equipped with everything you could possibly need and more! Fully stocked with kitchen appliances, spices, tea, coffee makers, bath towels, sheets, blankets, games, etc.. :) The space is cozy yet spacious with all the amenities to dine in, relax, walk to activities and enjoy!brbrPack your bags and enjoy a relaxing gateway!

2

Bed

1

Bath

4

Sleeps

$987.08

/ Nightly

Private Vacation Home

Cozy Westport Beachfront Retreat

Westport, Connecticut, United States

Welcome to your charming beachfront retreat! This cozy 4-bed, 2 full + 2 half bath home offers stunning water views from almost every angle and is just steps from the beach. Enjoy sun-filled spaces, a spacious living area, and a fully equipped kitchen. The basement includes laundry facilities, and there’s ample parking for 3-4 cars. Relax in the front yard or by the fire pit. Ideal for a comfortable, scenic coastal getaway.brbrInside, the spacious living area is filled with natural light and provides a comfortable spot to unwind. The fully equipped kitchen is perfect for preparing meals, which you can enjoy in the dining area or on the deck with the ocean as your backdrop.brbrThe master bedroom features a queen bed and a separate seating area ideal for watching movies or enjoying light reading. The second bedroom includes a full bed, while the third bedroom offers a single bed. The basement has been converted into a cozy space with a queen bed and an en-suite bathroom, providing extra privacy and comfort.brbrAdditional amenities include laundry facilities in the basement and ample parking for cars. Outside, relax in the charming front yard or gather around the fire pit in the evenings. There is access to a Weber grill on the porch, so your next family barbecue is well equipped. With the beach just steps away, you’ll have easy access to sand and surf for a perfect coastal getaway!brbrDowntown Westport, the Westport and Greens Farms Train Stations, and the I-95 are only minutes away. NYC is a 1 hr drive away.brbrExperience the best of beachside living, and book your stay today!

4

Bed

3

Bath

7

Sleeps

$4140.0

/ Nightly

Cottage

Historic oyster shack.

Westport, Connecticut, United States

Picturesque New England oyster farm cottage on a private island overlooking an intertidal salt pond. Built in the 1700s. Stay includes all you can eat oysters and private tour of the tidelands. Fun fact: Hummock Island Oyster Farm is a sustainable aquaculture operation run by a local family that has been in the business for over 100 years. The oysters are delicious and the property is one of a kind. Guests may also use the small oyster skiff.

Bed

Bath

Sleeps

$609.46

/ Nightly

Private Vacation Home

Designer Family Home with Gym and Yard

Westport, Connecticut, United States

Summary:brbrWelcome to this beautifully designed 3-bedroom family home in a stunning and affluent New England neighborhood. Centrally located between Compo Beach and downtown Westport, making this updated, airy and serenely comfortable space the perfect base for families or small groups exploring the area or visiting loved ones. Enjoy the home’s spacious living areas, sunken patio, fully equipped home gym & huge backyard with plenty of room for the whole family.brbrbrbrThe Space:brbrWhether you're looking to unwind or enjoy time with relatives and/or friends, this home has everything you need for an enjoyable and memorable stay.brbrbrbr• 3 comfortable bedroomsbrbr⎯▹ Bedroom #1: King sized bed, Smart TV + ensuite bathroombrbr⎯▹ Bedroom #2: XL full sized bed, swinging chair, workstation + closetsbrbr⎯▹ Bedroom #3: Full sized bed and closetbrbr• Each bedroom has plush linens + down comforter brbr• Pillows wrapped in silk pillowcasesbrbr• Well stocked, gourmet kitchen with including a Keurig & Nespresso machines brbr• Family room with large windows, skylights, lofty ceilings brbr• Three full bathrooms with showers, towels, and essentialsbrbr• Private front door entrancebrbr• Driveway parking for 1-2 cars. Ample street parking as well.brbrbrbr~ EXPERIENCE OVERVIEW ~brbr• Stylish 3BR home on a gorgeous and quiet New England streetbrbr• Fully equipped kitchen with modern appliances, including both coffee and espressobrbr• Spacious family room with high ceilings and skylightsbrbr• Home gym with padded floors, Pilates machine and free weightsbrbr• Sunken patio with lounge seating, dining table, and a grillbrbr• Large yard with trampoline for kidsbrbr• Close to Compo Beach and downtown Westportbrbr brbrThis home is minutes from Post Road groceries, restaurants and shopping, and centrally located in town between Compo Beach and Main Street,making it the perfect homebase to explore the area.brbrbrbr~ NEARBY ATTRACTIONS ~brbr» Downtown Westport → 5-minute drivebrbr» Compo Beach → 7-minute drivebrbr» Westport Country Playhouse → 4-minute drivebrbr» Sherwood Island State Park → 8-minute drivebrbr» Longshore Golf Course - 7 minute drivebrbr» Westport Train Station → 10-minute drivebrbrbrbr~ OUR FAVORITE LOCAL RESTAURANTS ~brbr» Terrain - 3 minute drivebrbr» Popup Bagels - 3 minute drivebrbr» The Granola Bar → 7-minute drivebrbr» Kawa Ni → 8-minute drivebrbr» Casa Me - 4 minute drivebrbr» Don Memo → 8-minute drivebrbr» La Plage → 6-minute drivebrbr» Bartaco → 9-minute drivebrbrbrbr~ OUR FAVORITE LOCAL DELIVERY ~brbr»Mecha Noodle Bar - Delivery, Uber Eats, Doordash, Postmates etc.brbr»Rainbow Thai - Delivery, Uber Eats, Doordash, Grubhub etc.brbr»Pizza Lyfe - Westport, dine in or call and pickup - 4 minute drivebrbrbrbr~ FAQS ~brbrIs the gym fully equipped brbr▹▹▹ Yes, the home gym includes a Lagree Pilates machine, free weights, yoga balls, and a TV with Apple TV.brbr brbrAre there laundry facilities brbr▹▹▹ Yes, there is a laundry room with a washer and dryer available for guest use.brbr brbrHow far is the home from the beach brbr▹▹▹ Compo Beach is a short 7-minute drive away, perfect for a quick beach day.brbrNOTE: All local beaches in the area require a residential sticker to park between May and October Or you can pay the hefty daily fee. Ride Share from a nearby restaurant after brunch is usually our suggestion.brbrbrbr♥ A NOTE FROM YOUR HOSTS ♥brbrWe're excited to welcome you to our Westport home! Whether you're here to relax, explore the area, or enjoy the beach, we're here to make sure your stay is perfect. If you need anything at all, just let us know—we're happy to help!brbrbrbrSincerely,brbrYour Hosts, Janelle + Alexbrbrbrbr-Owners @ The Styled StaybrbrbrbrGuest Access:brbrA smartlock on the front door will be delivered on check in and valid until checkout. Parking will be available in the carport. Garage access may be available - but is not guaranteed, please inquire if it is essential.brbrbrbrThe Neighborhood:brbrOur home is on an absolutely gorgeous and quintessential New England street bordered on all sides by large, 2M+ homes. It is centrally located so it is very close to downtown, multiple restaurants and beaches!brbrbrbrGetting Around:brbrYou'll need a car to get around and there is parking for 2 of them in our driveway without anyone being blocked in. Biking around town is also great as most all the surrounding roads are flat and smooth.brbrbrbrOther Things to Note:brbrThere is a studio apartment on the lower level that is rented out separately or can be included for additional cost and larger parties. It has its' own private entrance and are no shared spaces other than the driveway. brbrbrbrA hypoallergenic 9lb maltipoo does live in the space for anyone who has severe allergic reactions to pet presence.brbrbrbrInteraction with Guests:brbrI am not on the premises but available via phone, Airbnb messaging or please text me for anything urgent. If needed, I have multiple local people to call on for help to address any issues that are interfering with the enjoyment of your stay.

3

Bed

3

Bath

5

Sleeps

$484.64

/ Nightly

Cottage

DIRECT WATERFRONT Beachhouse!

Westport, Connecticut, United States

Quintessential New England Beach Cottage, just 1 mile to the Westport train station, great restaurants & town shopping! A local Interior Designer's own, this original 1900 Beach Charmer was built NEW from top-to-bottom complete with a new kitchen with big island and stainless steel appliances, two new baths; new hardwood floors and all new windows. Designer furnished for stylish but comfortable living, this cottage includes a large Master Bedroom with plenty of closets and an office/2nd bedroom with bunkbeds for the kids. Views abound from all the windows in the Great Room which is complete with a remote fireplace and plenty of comfortable seating for family & friends.brLiterally steps to the water to swim, kayak, sail or paddleboard. brHang out on the front porch with your morning coffee or evening cocktail or to just watch the crew teams row; the sail teams sail, the jet-skiers zip around, and the constant stream of boats- both big & small going in & out of the Marina, as well as many bikers and runners alike. Enjoy the NEW 20 x 20 Rooftop Deck overlooking the water. brMooring available for an extra fee; literally just 50’ in front of the house!brThis perfect little getaway is located at water's edge sandwiched between the Saugatauk Marina and the Cedar Point Yacht Club with steady marine activity. brMinutes from the Westport Train Station for NYC commuters to Grand Central. Perfect for the relocation of out-of-town company employees.brAll you need is LOVE & the BEACH.

Bed

Bath

Sleeps

$1610.0

/ Nightly

Private Vacation Home

Spacious 5-bedroom house in Westport with fitness room, pool and home theatre.

Westport, Connecticut, United States

Imagine a peaceful oasis of tranquility, right in the very center of Westport. This home is nestled on an acre of park-like property with extensive landscaping, stunning stone patios and a sparkling gunite pool with spa and auto cover. This remarkable property is the ultimate getaway, yet is walking distance to shops, conveniences, and restaurants and a 6 minute drive to the beach, Longshore, downtown Westport and both Metro North Railroad stations. Open kitchen / family room is the heart of the home. Spacious bedrooms (1 king bed, 2 queens, 2 twin beds an additional upstairs sleeping space for kids) provide room for everyone along with 6 baths. Great bonus play spaces, media room, home gym and so much more. Kickback, relax, and enjoy everything Westport and this house has to offer.

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Bath

Sleeps

$1,337

/ Nightly

Private Vacation Home

Private Oasis: Completely Renovated Old Farmhouse With Pool And Guesthouse

Westport, Connecticut, United States

A private oasis for fine living, this pristine antique farmhouse is on over an acre of breathtaking property featuring magnificent perennial gardens, stone terraces, rolling lawns, an inviting pool and pool house. Completely renovated and expanded in 2009, you will find the the charm and character of an old house with mid-century modern furniture and state-of-the-art amenities. The living room, library and dining room flow seamlessly together providing a perfect setting for a family gathering still giving everyone lots of privacy. The gorgeous sun filled gourmet kitchen, breakfast room and family room anchor the main floor of the home and handle the hub of activity effortlessly.

4

Bed

4

Bath

8

Sleeps

$2058.5

/ Nightly

Private Vacation Home

Westport Dream Home 6 Bedroom / 5 BathroomnnPool and Jacuzzi nnSteps to town

Westport, Connecticut, United States

Unwind in Westport at this dream house. brbrWith 6 bedrooms, 5 bathrooms, and a newly put in Salt Water pool, stone Jacuzzi Restoration Hardware outdoor Firepit brbrThe best part is location steps away from Downtown buzzing Westport and minutes to the Beach!

Bed

Bath

Sleeps

$1577.0

/ Nightly

Private Vacation Home

Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth

Westport, Connecticut, United States

Westport Perfection. One of the most desirable homes in Westport situated on one acre. Located on one of the best streets in Westport. New pool, hot tub, patio installed for Spring 2025. 5 minutes to beach, train and grocery. Highest end furniture in every room. 5 bedrooms, 6 baths. Playroom, finished basement. All the toys your children could want - ping pong, bikes, scooters, games and more. Available for summer rental.

Bed

Bath

Sleeps

$226.26

/ Nightly

Apartment

Spacious Studio with Pool Table

Westport, Connecticut, United States

Summary:brbrEscape to your private Westport studio retreat in one of the most desirable neighborhoods in town! This stylish space comfortably sleeps 2 guests and is perfect for fun and relaxation. Unwind with your own private pool table, a cozy home theater, and a dedicated workspace. Centrally located between Compo Beach and Downtown, it's the ultimate getaway for couples or small groups seeking a unique and entertaining stay.brbrbrbrThe Space:brbrDesigned as a private home away from home, the open-plan space includes several distinct areas for you to enjoy. Unwind in the comfortable lounge, challenge a friend to a game on the full-size pool table, or settle in at the dedicated work desk complete with an iMac and fast Wi-Fi.brbrbrbrThe sleeping area features a comfortable queen-size bed, and the modern bathroom includes a walk-in shower and all the essentials. A kitchenette cart with a mini-fridge is perfect for storing drinks and light snacks.brbrbrbrYour stay includes:brbr* Queen-size bed with fresh linensbrbr* Full-size pool tablebrbr* Lounge with a smart TV and home theater setupbrbr* Dedicated workspace with an iMacbrbr* Kitchenette with mini-fridge and coffee stationbrbr* Bathroom with shower, fresh towels, and essentialsbrbrbrbrThis home is centrally located between Campo Beach and Downtown Westport, making it the perfect base to explore the area. Perfect for solo travelers or couples.brbrbrbr~ NEARBY ATTRACTIONSbrbrbrbr» Downtown Westport → 5-minute drivebrbr» Compo Beach → 7-minute drivebrbr» Westport Country Playhouse → 4-minute drivebrbr» Sherwood Island State Park → 8-minute drivebrbr» Longshore Golf Course - 7 minute drivebrbr» Westport Train Station → 10-minute drivebrbrbrbr~ OUR FAVORITE LOCAL RESTAURANTSbrbrbrbr» Terrain - 3 minute drivebrbr» Popup Bagels - 3 minute drivebrbr» The Granola Bar → 7-minute drivebrbr» Kawa Ni → 8-minute drivebrbr» Casa Me - 4 minute drivebrbr» La Plage → 6-minute drivebrbr» Bartaco → 9-minute drivebrbrbrbr~ OUR FAVORITE LOCAL DELIVERYbrbrbrbr»Mecha Noodle Bar - Delivery, Uber Eats, Doordash, Postmates etc.brbr»Rainbow Thai - Delivery, Uber Eats, Doordash, Grubhub etc.brbr»Pizza Lyfe - Westport, dine in or call and pickup - 4 minute drivebrbrbrbr~ FAQSbrbrbrbrIs the studio suitable for remote work brbr▹The studio includes a dedicated workspace with an iMac and fast Wi-Fi for all your remote work needs.brbrbrbrHow far is the beach brbr▹ Compo Beach is just an 8-minute drive from the studio, perfect for a quick seaside escape! NOTE: All local beaches in the area require a residential sticker to park between May and October Or you can pay the hefty daily fee. Ride Share from a nearby restaurant after brunch is usually our suggestion.brbrbrbrAre there laundry facilities available brbr▹ While there’s no in-unit laundry, local laundromats and laundry services are available nearby.brbrbrbrCan I fit 3 or 4 people brbr▹ The studio is really for double occupancy so if you do have a 3rd or 4th person, please request our queen sized aerobed in advance. There is also a 3 seater couch for one additional person to sleep.brbrbrbr♥ Meet Your HostsbrbrbrbrWe’re excited to welcome you to our cozy studio in Westport. Whether you're here to relax or explore the town, we hope you feel right at home! If you need anything during your stay, don’t hesitate to reach out — we’re happy to help!brbrbrbrSincerely, brbrYour Hosts, Janelle + Alexbrbrbrbr-Owners @ The Styled StaybrbrbrbrGuest Access:brbrYou will have complete and private access to the entire studio apartment. Your private entrance is located to the left of the garage, through a gate marked with an 'X'. For a seamless check-in, your unique smart lock code will be sent 30 minutes before your scheduled arrival time.brbrbrbrPlease note that other than the direct path to your private studio door, the outdoor space is off-limits and reserved for the residents of the upper unit.brbrbrbrThe Neighborhood:brbrThe studio is located in a quiet Westport neighborhood, just minutes from downtown, beaches, and parks. You'll be close to everything Westport has to offer while enjoying the peaceful surroundings.brbrbrbrGetting Around:brbrThe studio is conveniently located near major highways, making it easy to explore the area. Both I-95 and the Merritt Parkway (Exit 18 and Exit 42) are nearby. Parking is available in the driveway for up to two cars.brbrbrbrOther Things to Note:brbrA few important details to ensure you have the best possible stay:brbr* **Unit Location:** This studio is the private lower-level unit of a home. As is common in multi-level homes, you may hear noise from the upstairs residents, such as foot traffic or floor squeaks. We are transparent about this to ensure your expectations are set for a comfortable stay.brbr* **Occupancy:** The studio is designed for double occupancy (2 guests). We can accommodate up to 4 guests for an additional charge per person, per night. An air mattress and/or bedding for the couch can be provided upon request.brbr* **Laundry:** While there are no laundry facilities in the unit, several local laundromats and laundry services are available nearby.brbr* **Booking:** A pre-arrival form and ID verification will be requested upon booking.brbrbrbrHouse Rulesbrbr✓ No petsbrbr✓ Quiet hours: 10:00 PM - 7:00 AMbrbr✓ No parties or eventsbrbr✓ No commercial photography or videographybrbr✓ No smoking of any kind inside the studio or outsidebrbr✓ Other than to access the studio door, the outdoor space is off-limits to renters.brbrbrbrInteraction with Guests:brbrWe respect your privacy and offer a seamless self-check-in process. While we may or may not be present during your stay, we are always available and happy to assist with any questions or recommendations via the app. Our goal is to ensure you have a comfortable and enjoyable stay.

1

Bed

1

Bath

4

Sleeps

$151.42

/ Nightly

Apartment

Cozy Apartment in Downtown Westport

Westport, Connecticut, United States

This cozy historic home synchronizes the entertainment, calm and beauty of Westport. With one of the best locations in Westport (and two bikes for excursions) you will be walking distance to all that Downtown Westport has to offer and just an 8 minute drive to Compo Beach, while having a peaceful retreat to come back to.brbrNewly renovated antique carriage house. One bedroom apartment sleeps 2-3; brand new queen sized memory foam bed, living room, kitchen (with oven, microwave, refrigerator, toaster, coffee maker, dishes, utensils, and pot/pans), and full bathroom. The living space has a large TV and wireless internet access. The back porch and backyard area are a peaceful oasis with a gas grill, table, and two chairs. The downstairs garage contains two bikes for your use. Close to public transport, shopping, & eats! You’ll love my place because of the location and the ambiance.brbrThis charming, private stand-alone apartment is completely yours to enjoy. It includes a private entrance, parking, and backyard grill and porch sitting area in the rear of the building for your sole use.

Bed

Bath

Sleeps

$503.4

/ Nightly

Cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage

Westport, Connecticut, United States

Our charming beach cottage is available in the exclusive Saugatuck Shores area, literally steps to the water (150 steps to be exact!). The neighborhood is great for walking, running, biking and water sports. The house is located on a peninsula, so there is water at every turn. You can experience the truly spectacular morning sunrises and afternoon sunsets. In the summer, walks to the yacht club for an informal lunch or lounging on the several small beaches nearby are lovely ways to spend the day. Our cottage is located within easy distance of the highways (I-95 and the Merritt Parkway), the train station and the downtown areas of Westport and South Norwalk with all their shops and restaurants.brbrOur home is sweetly decorated and has been curated with relaxation and beach living in mind. It has three bedrooms downstairs, each with a queen bed. Upstairs is an entire second floor loft space done in bright white strips with a large desk and an oversized pouf - ( there are no beds in this space any longer). brbrThere are two bathrooms with Waterworks and Restoration Hardware fixtures and a petite yet gourmet kitchen with Italian marble countertops, stainless steel appliances, a farmhouse sink and a Viking range. The dining alcove is especially sweet as it is strewn with seashells. There are two enclosed porches plus an extra large yard fenced yard with outdoor grill.brbrCloud 9 is the perfect place to rest your head while in town for business or pleasure. brbrRentals longer than 1 month may be subject to different pricing and utility inclusions / exclusions. brbrThe furniture changes frequently as we are decorators and are continually imbuing the space with fantastic finds - what remains is the charm and serene energy surrounding the cottage.brbrSAME DAY BOOKINGS WELCOME if we have availability. Homeaway does not allow this automatically so reach out to us if this is your situation. brbr***Fall 2024*** Our calendar is set to accommodate one month stays or longer to prevent any short term booking issues with Homeaway - which happen quite often for both travelers and owners. Feel free to write us for a shorter stay. If we can accommodate you, we will try. brbrThe calendar is blocked from March 1, 2025, onwards. This does not mean we are booked. Please inquire about 2025 stays.brbrThank you and Namaste.

3

Bed

2

Bath

4

Sleeps

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