Vacation Rentals By Owner In Weston, CT

You would love living in this waterfront, serene space-A great place to relax and recharge. Sip a favorite drink sitting on your own deck with river view or on a bench next to the river-watch dears drink water and ducks swim by. Sometimes you wouldsee a bear. It’s a 225 year old house. Almost all the wooden structure is the original wood. countryside and still close to many major cities (Manhattan is one hour-which is same distance as from Queens, Brooklyn and some Northern parts of Manhattan).brbrClose to downtown Westport, route 15 and I-95. Almost all of the Weston houses have 2 acres or more land, worth over a million dollars. Surrounded by many large estates, golf courses, parks.brbrStructure and the layout of the house reflects the era of close knit families in cosy rooms.

50%OFF Riverfront WestonHome 1.6 Acers-NYC 1 hour Near estaurants I-95& Parkway

Weston, Connecticut, United States

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Exceptional(4)

$95.83

Simple, clean, freshly painted room on the ground floor, with a bed, a work desk, a love seat, a small closet and shelves. A private entrance/exit with no stairs leads through the garden to the driveway. The bathroom has a standup shower and a window to the backyard. The owner lives in the house but the room/bath are completely private.

A private room for any traveler

Weston, Connecticut, United States

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$145.8

Nestled in top rated Weston CT, this beautiful studio offers a cozy and inviting space perfect for a relaxing stay. We welcome long term renters. You'll have a spacious private bathroom with a refreshing shower and handy hair dryer. The studio stays comfortable year-round with heating and AC, making it easy to unwind no matter the season. Whether you’re freshening up with the iron or getting ready for a day out, this amazing spot has you covered. The kitchen is fully equipped to prepare warm meals. Two closets for storage and a Smart TV to watch your favorite series or movies. Kickback, relax, and enjoy everything Weston Woods and our studio has to offer.

Apartment

Relaxing studio in weston woods

Weston, Connecticut, United States

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Exceptional(13)

$431.25

Welcome to our private guest cottage in the charming town of Weston, CT. Located about 45 miles from NYC, this is the perfect getaway.brOur enchanting two-bedroom cottage is perched near the tranquil Saugatuck River—one of Connecticut's finest trout fishing havens. A mere stroll from the cottage, this river setting offers a perfect blend of leisure and nature's charm. br brOur 1000-square-foot cottage features two cozy bedrooms, each furnished with comfortable double beds, ensuring a restful night's sleep. Guests will appreciate the brand-new bathroom, complete with a modern shower, blending comfort with convenience. br brThough compact, the kitchen has all the necessary amenities for a delightful home-cooking experience. It's perfect for preparing meals to enjoy indoors or by the riverside.br brThe living room is a hub of relaxation and entertainment, offering Wi-Fi and a large-screen TV, ideal for movie nights or staying connected.br brStep outside to enjoy our nearby expansive fire pit area next to the river. It's a splendid spot for gathering, complete with chairs and firewood for those starlit nights. br brIn addition to the natural beauty, we also offer a unique service for couples looking to tie the knot. Our picturesque back lawn, with the river's soothing presence, provides a romantic setting for intimate wedding ceremonies. We also have a resident Justice of the Peace.br brFor those seeking adventure, superb hiking trails including one just down the street ( Trout Brook Valley, which is dog friendly) , offer various experiences from peaceful walks to more vigorous treks.br brOur cottage is set in an atmosphere of warmth and relaxation. As hosts, we are readily available to ensure your stay is comfortable and fulfilling. Experience the allure of Weston and the unique charm of our riverside cottage for a truly unforgettable getaway.brDue to cleaning crew schedules, we can't accommodate late check-outs.br brGuest accessbrThe entire guest house and shared riverside lawn and fire pit are available to guests which is 75 yards away.br

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break

Weston, Connecticut, United States

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$309.55

Nestled in Weston, CT this delightful house offers a pleasant stay for guests. With 2 cozy bedrooms featuring a queen bed and a full bed, along with a well-equipped kitchen, this welcoming property ensures a comfortable experience. Whether you're looking to relax in the charming living space or explore the nearby attractions, this perfect retreat has everything you need for a memorable getaway. brOn the first floor we have the living room, dining room, open kitchen concept with range, dishwasher, double oven, fridge, microwave, toaster, coffee maker, blender, kitchen aid mixer, a closet for coats and storage. brOn the second floor we have the master bedroom with a queen bed, another bedroom with two full size beds and a full bathroom.brThe barn is used as recreation space with a toilet, sink, ping pong table, futbolin, personal sauna, stationay bycicle, and some table games.brThere is an above ground pool with a deck and a patio with a BBQ and table for 6 persons.brThere is a camera system outside the house for security.brWe're happy to assist with any questions while you stay at our house.

Cozy, fully renovated 2BR home with a barn in peaceful Weston, CT for relaxation

Weston, Connecticut, United States

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Exceptional(2)

$1623.69

As seen in dozens of national shelter magazines (such as House Beautiful and Country Home) over three decades, this charming English-style cottage is nestled in the woods, a stone's throw from the river's edge, and filled with sunlight.brbr-Total privacybr-Bon Appetit magazine's Kitchen of the Yearbr-Large stucco living room with cathedral ceiling, hand-hewn beams, and rubble stone fireplacebr-Fir floors throughoutbr-Generously sized eat-in screened porch for outdoor entertaining (14' x 28')br-Large backyard with a hammock tied between two treesbr-Outdoor laundry line in the front to dry your linens in the fresh airbr-Light-filled sunroombr-Wallpapered bedroomsbr-Two en-suites (one with separate entrance on first floor and the other with cathedral ceiling and large terrace (to enjoy breakfast or sunbathe) on the second floor. br-Two full beds, two king bedsbr-Access to private community beach, swimming, kayaks, clay tennis courts, playground, and basketball courtbr-Weber Sumit platinum barbecue grill with 36 grill space and 12 cooktopbr-2 miles to closest farmstand, 4 miles to downtown Westport, 7 miles to Metro North train station (1 hour train ride to New York City)br-8 miles to Compo beach, 10 miles to Fairfield beachbr-Weston and Westport Farmers Market, 5 more neighboring weekly farmers marketsbr- Westport's Levitt Pavilion: outdoor venue for live music and events br- Nature Trails and Water Falls

Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn

Weston, Connecticut, United States

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Exceptional(2)

$468.75

2 Covered Patios | Home Library (Accessible via Bedroom 3) | Pet Friendly w/ FeebrbrExperience the perfect blend of historic charm and modern luxury at this peaceful Weston retreat — ideal for families and friend groups seeking comfort, style, and easy access to outdoor adventure. Thoughtfully designed for relaxation, the home features a fully equipped kitchen, two covered patios, a grill, and a sprawling yard that invites you to unwind and reconnect after a day of exploring.brbrSpend your days discovering nearby highlights like Devil’s Den Preserve for scenic hikes, Beardsley Zoo for family fun, or browsing fresh local finds at the Grace Farms farmers market. Then return to your private haven to relax by one of the decorative fireplaces, enjoy a board game, or settle in with a good book.brbrOutdoor Living:brGrill, furnished patios for dining and lounging, expansive landscaped yardbrIndoor Living:brFlat-screen TVs with cable, 3 decorative fireplaces, board games, books, two workspaces with desks and monitor, multiple dining areas, spa-style bathrooms with walk-in and tub/shower combosbrKitchen:brFully stocked with double oven, stovetop, refrigerator, dishwasher, microwave, Crockpot, mixer, SodaStream, coffee maker & grinder, water filter, plus all cookware and essentialsbrGeneral Amenities:brFree WiFi, central air conditioning, radiant heat throughout, washer/dryer, linens and towels, complimentary toiletries, hair dryer, steamer, iron & board, hangers, and essential suppliesbrWhether you're savoring morning coffee on the patio or gathering for an evening meal, this refined retreat offers a serene escape with all the comforts of home.brbrBedroom 1: King BedbrBedroom 2: Queen BedbrBedroom 3: King BedbrBedroom 4: (Accessible via Bedroom 3) - Twin Daybedbrbr- No smokingbr- Pet friendly br- No events, parties, or large gatheringsbr- NOTE: The 3 fireplaces are not available for guest use

Charming Historic Connecticut Home W/Spacious Yard

Weston, Connecticut, United States

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Exceptional(6)

$1183.03

Rare, newly re-constructed 4 bedroom plus office 4.5 bath residence with heated pool and hot tub is perfectly outfitted for your valuable r & r. This mid-century modern home offers 2 bedrooms with 2.5 baths on the main level and 2 more bedrooms with 2 bathrooms upstairs. The home has extensive southern exposures and ton of windows; hence it gets great light. House sits on a 2-acre leveled lot. There is a brand new 5 person hot tub (open year round) and newly redone in ground heated pool with outdoor heated shower (seasonal). The house is furnished with designer furniture and accessories. Two large TVs (75 & 65 inch) and propane BBQ grill. This one of a kind property is located close to town, beaches, restaurants & the Westport train station is 15 minutes away. No pets permitted, sorry:). Maximum capacity is 8 people inclusive of children. brbrSummer rentals will include an energy deposit (pool heater propane/electric) for which the unused portion will be refunded.

Modern 4 bed 4.5 bath w hot tub & heated pool close to beach

Weston, Connecticut, United States

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$167.94

studio apartment meaning a single room combining living, sleeping, and kitchen areas (but a separate bathroom). Essentially, it's a compact, open-plan dwelling, often smaller and more affordable than a one-bedroom

Small apt Bathroom & Kitchen.

Weston, Connecticut, United States

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$162.67

A private, self-contained home within a larger residential building. Comes with everything you need to live day to day - your own kitchen, bathroom, and one or more living spaces. Designed for long-term stays and offer a more stable housing solution.brbr-Easy Check-In. br-Near Norwalk, Wilton, & Westport.br-Nearby hiking + reservoir. br-60 minutes to NYC

Apartment in ct

Weston, Connecticut, United States

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$537.5

River retreat access in a serene and joyful historic district. Unique inspiring office overlooking nature. Central AC. Special attention has been placed in the choice of luxury and ultra-comfortable mattresses and pillows. 12 min away from downtown Westport restaurants. 15 minutes to lovely Compo Beach. 15 away min from Connecticut’ largest nature preserve. The whole house has been filtered for EMF and has ultra low emission. 2 working fireplaces. 4 Bedrooms. Master bedroom, king bed and 2 en suite bathroom with tub. Two guest room bedroom, queen bed, each with en suite full bathroom with shower. 1 Twin Bedroom. 2 working fireplaces.brbrOne Gourmet kitchen overlooking the garden (you can enjoy looking at birds while you prepare your coffe and meals. Two offices, one with extraordinary view on nature, the other petit with view on the back garden.brbrLiving room. Den/TV room. Powder room. 3 gardens. The 3rd garden, across the street, has a dock on the pristine Saugatuck River.brbrSummer rental comes with a free month pass for the famous Compo Beach (value: 415.00 USD per month).***brbrbrThis historic house has incredible charm, and the interiors have important selected art and design fornitore. All bedrooms have luxury mattresses and pillows. Very important for your relaxation and wellness (especially if this house if for you to take a break from a city) the owners are themself EMF sensitive so this is EMF home: the entire property has been shielded with 20 Stetzer Filters. You are 15 minutes away from the Lucius Pond Ordway/Devil's Den Preserve: Connecticut Chapter's largest continuous preserve and the largest tract of protected land! As well as the Saugatuck Reservoir and the The Centennial Watershed State Forest (15,000 acres).brbrProfessional cleaning, one a week, included in the monthly price. Passes to the famous Compo Beach included*** Stunning & inspiring office overlooking nature. Special attention has been placed in the choice of luxury and ultra-comfortable mattresses and pillows.brbrThere are 3 private parking spots and one garage.brbr*** Beach access included! As part of your monthly rental, we're happy to provide daily beach access pass to beautiful Compo beach.brThe passes are valued at $45 on weekdays and $70 on weekends/ holidays. For a one month stay we'll cover up to $450 in beach access. For a two month rental, the cap increases to $900.

1845 Historic & Romantic Westport/Weston River Access - Luxury Matresses Low EMF

Weston, Connecticut, United States

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Exceptional(41)

$231.92

Kick back and relax in this calm, stylish cottage located in Weston, CT with 1 bedroom, 1 bathroom, fully equipped kitchen, living-room and mezzanine that can accommodate one more person (daybed) or can be used as a most peaceful work area. All surrounded by woods, yet 15 minutes to train station (1hr 10 min to Manhattan), shopping areas and a beautiful beach.

Adorable 1-Bedroom Cottage in Weston, CT

WESTON, Connecticut, United States

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Exceptional(12)

$467.08

Historic charm meets upscale comfort at this serene Weston vacation rental — where families and groups of friends can enjoy at-home amenities and easy access to an abundance of outdoor activities. With a fully equipped kitchen, 2 covered patios, a grill, and a spacious yard, this home provides a comfortable place to unwind after a day’s adventures. Enjoy a scenic hike at Devil’s Den Preserve, take the kids to Connecticut’s Beardsley Zoo, or stop by the local farmers market at Grace Farms!brbr-- THE PROPERTY --brbr2 Covered Patios | Home Library (Accessible via Bedroom 3) | Pet Friendly w/ Fee brbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: King Bed | Bedroom 4: (Accessible via Bedroom 3): Twin DaybedbrbrOUTDOOR LIVING: Grill, outdoor seating & dining, spacious yardbrINDOOR LIVING: Flat-screen TVs w/ cable, 3 fireplaces (decorative), 2 desks, monitor, 2 dining tables, breakfast bar, walk-in shower, shower/tub combo, board games, books brKITCHEN: Stovetop, double oven, refrigerator, dishwasher, cooking basics, dishware/flatware, drip coffee maker, coffee grinder, SodaStream, microwave, Crockpot, mixer, water filterbrGENERAL: Free WiFi, central A/C, radiant heating (entire house), complimentary toiletries, hair dryer, washer/dryer, clothes steamer, iron/board, hangers, linens/towels, trash bags/paper towels brFAQ: Doorbell camera (facing front entryway), pet fee (paid pre-trip)brACCESSIBILITY: 3-story home, 4 steps to enter, half bath on 1st floor, interior stairs required to access all bedrooms & bathrooms on upper levelsbrPARKING: Driveway (3 vehicles), RV parking allowed on-sitebrbr-- THE LOCATION --brbrATTRACTIONS: Devil’s Den Preserve (4 miles), Sherwood Island State Park (6 miles), Weir Farm National Historic Park (8 miles), Saugatuck Falls Natural Area (10 miles), The Maritime Aquarium at Norwalk (10 miles), Connecticut’s Beardsley Zoo (16 miles)brFARM FRESH: Silverman’s Farm (12 miles), Grace Farms (14 miles), Plasko’s Farm Creamery & Cafe (16 miles), Harvest Moon Farm & Orchard (28 miles)brGONE FISHING: Trout Brook Valley Preserve (5 miles), Saugatuck Reservoir (5 miles), Mill Pond Park (7 miles), Norwalk Beach Pier (10 miles), Lake Mohegan Recreational Area (10 miles), Lt Owen Fish Park (11 miles) brAIRPORTS: Westchester County Airport (24 miles), Bradley International Airport (79 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- Pet friendly w/ $75 fee (+ fees & taxes)br- No events, parties, or large gatherings br- Must be at least 25 years old to book br- Additional fees and taxes may apply br- Photo ID may be required upon check-inbr- NOTE: This 3-story home requires 4 steps to enter. While it features a half bathroom on the 1st floor, interior stairs are required to access all of the bedrooms and bathrooms located on the upper levelsbr- NOTE: The 3 fireplaces are not available for guest use br- NOTE: Your safety matters. This property features a doorbell device with an exterior security camera facing the front outdoor entryway. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion

Historic Connecticut Home w/ Grill & Spacious Yard

Weston, Connecticut, United States

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Welcome to our private guest cottage in the charming town of Weston, CT. Located about 45 miles from New York City, this is the perfect getaway from the hustle and bustle of city life. The cottage has two bedrooms (one queen bed, one full bed), two full bathrooms, a sitting room and large open living/dining/kitchen area with a cathedral ceiling and gas fireplace. There is a stone patio and a pool for enjoying the summer days. Please note that we do not allow parties at the cottage.brThe spacebrThis light and airy space offers a quiet spot to get away. Close to great hiking and lots of restaurants and shopping, the quiet town of Weston if the perfect spot to explore surrounding towns and beaches including Westport and New Canaan.

Weston Cottage/Guest House

Weston, Connecticut, United States

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Four bed colonial house, in peaceful lower Weston with swimming pool and 2 acres of garden. Short drive to Compo beach and Westport town center. Close to magnificent hikes and lovely local walk in close by park.

Peaceful farmhouse style with pool and 2 acres of garden

Weston, Connecticut, United States

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This memorable house is the perfect home base for your trip to Weston. With 5 bedrooms including 1 king bed, 2 queen beds, 1 twin bed, and 1 full bed, this gorgeous property offers plenty of space for guests to relax and unwind. Complete with two playrooms and outdoor dining area your family will be ready to enjoy summer. Close to Westport town line and access to compo beach in Westport

Spacious 5-bedroom family house in fabulous Weston

Weston, Connecticut, United States

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Set in 2 acres of beautiful garden with gardened swimming pool, this spacious 4 bed house is an oasis of tranquility. There is a large deck which overlooks the pool. About 5 miles to Compo Beach and lots of hiking trails nearby. 4 minute drive into Westport.

Stunning Weston 4 bed house with swimming pool

Weston, Connecticut, United States

Bed

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Exceptional(3)

$1111.61

Forget your worries in this spacious and serene space. A sparkling, sweeping, sunny, and inviting contemporary home just waiting for you to enjoy. The open first floor plan features soaring vaulted ceilings with skylights that flow from the fireplace-adorned great room to dining room to chef’s kitchen, creating a casual, but effortlessly elegant gathering space for family and friends. Enjoy playing tennis and pickle-ball on the newly refreshed har-tru court before dipping into a relaxing hot tub.

Gorgeous Weston Retreat with Tennis & Hot Tub

Weston, Connecticut, United States

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$407.8

Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access, The River Loft is a hidden gem. Book now for an enchanting getaway and an unforgettable experience.

Escape to The River Loft, a secluded private riverfront retreat in Weston, CT.

Weston, Connecticut, United States

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Most popular vacation rentals in Weston

$309.55

Cozy, fully renovated 2BR home with a barn in peaceful Weston, CT for relaxation

Weston, Connecticut, United States

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Sleeps

$1623.69

Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn

Weston, Connecticut, United States

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Sleeps

$1111.61

Gorgeous Weston Retreat with Tennis & Hot Tub

Weston, Connecticut, United States

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$718.75

Feist House - Hot Tub + Beach Retreat in Nature

Weston, Connecticut, United States

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$634.80

Charming 3-bedroom Ranch in Weston Near Westport & Fairfield

Weston, Connecticut, United States

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$468.75

Charming Historic Connecticut Home W/Spacious Yard

Weston, Connecticut, United States

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Sleeps

$467.08

Historic Connecticut Home w/ Grill & Spacious Yard

Weston, Connecticut, United States

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$431.25

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

Weston, Connecticut, United States

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$407.80

Escape to The River Loft, a secluded private riverfront retreat in Weston, CT.

Weston, Connecticut, United States

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$325.88