Are there pet-friendly vacation rentals in Weston?

Four-legged friends are welcome in Weston. Choose from more than 20 vacation rentals for guests traveling with pets.

Are there vacation rentals with a dedicated workspace in Weston?

Yes! Work meets play with ease at over 40 vacation rentals in Weston featuring dedicated workspaces. Stay connected and productive in your home away from home.

Do house rentals in Weston have a gym?

Absolutely! We offer over 10 house rentals with a gym in Weston. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Weston have air conditioning?

Absolutely! We offer over 40 house rentals with air conditioning in Weston. Enjoy a tailored experience with all the comforts you desire.

How much does it cost to stay in house rentals in Weston?

Experience the best of Weston with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Do house rentals in Weston have wifi?

Absolutely! We offer over 40 house rentals with wifi in Weston. Enjoy a tailored experience with all the comforts you desire.

What are the most popular amenities for House Rentals in Weston?

Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 40 homes with wifi, over 40 homes with air conditioning, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Are there family-friendly vacation rentals in Weston?

Weston has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Do house rentals in Weston have a bbq area?

Absolutely! We offer over 10 house rentals with a bbq area in Weston. Enjoy a tailored experience with all the comforts you desire.

Are there Weston vacation rentals on Airbnb with pools?

Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Weston, available on Airbnb. Make a splash and soak up the sun in style!

Vacation rentals in Weston

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Weston

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

The entrance features a charming porch framed by white railings, with potted plants adding greenery. A welcoming front door is accentuated by patriotic decorations, and a small seating area is visible beside lush greenery and a well-maintained lawn.

Home in Fairfield

4.9 out of 5 average rating, 113 reviews

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking

ENTIRE 2nd FL for up to 2️⃣ adult guests ONLY 2️⃣ Rooms➕Skylit Full Bath Exclusive Driveway Parking spots➕Private Main Entrance, separate from full-time renters on 1st FL using back entries Heat & Cool: wall-mounted AC➕portable Dyson ➕ Central AC w/2 sensors - host adjustable remotely TV is Screen only, works with Bluetooth & Chromecast, NO Services Kitchenette: heat/store food (NO cooking), allows affordable stay in affluent Fairfield Town Professional Clean Service Host Assistance Virtually

Top guest favorite

The guesthouse exterior showcases a stone facade complemented by a sloped roof. A large patio area with an umbrella provides shade over a picnic table, surrounded by well-maintained greenery and trees. A natural stone wall lines the property, enhancing the outdoor living space.

Guesthouse in Weston

4.98 out of 5 average rating, 44 reviews

Nature Lovers Guesthouse

This beautiful Guesthouse is a perfect city escape for taking in nature. Located near amazing hiking, fishing, and parks, while just a 15-min drive to beaches, shopping, and dining. A cyclist's dream, located right on scenic route 53! The Guesthouse sits apart from the famous main Log Cabin providing serene views of the garden, pond, waterfall, and stream. You may even recognize this historic property from a Ralph Lauren ad or the 1975 film The Stepford Wives! Please read 'Other details to note'

Guest favorite

A spacious bedroom features a queen-sized bed with a light-colored quilt. Two elegant armchairs are positioned around a glass-topped table. Natural light floods in through multiple windows adorned with lace curtains, providing views of the verdant surroundings.

Guest suite in Fairfield

4.92 out of 5 average rating, 153 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; exclusive use of kitchen (was the main kitchen of the house); private entrance to space thru side door of the house. Two large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Top guest favorite

A view from a staircase leads to a private patio area featuring a table and an umbrella. Lush greenery frames the scene, with green flowers visible in the foreground. The patio is designed for outdoor enjoyment, set within a tranquil, secluded backyard.

Guest suite in Weston

5 out of 5 average rating, 43 reviews

August Dates Open! Private Suite 5 Min to Westport

Welcome to your private garden-level retreat in Weston CT. An artfully designed suite by an artist and designer. With its own entrance, secluded patio with wooded, peaceful surroundings, this curated space blends comfort, style, and serenity. Just minutes from Westport, it offers an award-winning mattress, a cozy lounge area, organic coffee bar, high-speed WiFi, and more. Calm, clean, and thoughtfully designed. Guests describe it as peaceful, beautifully styled, and full of thoughtful touches.

Guest favorite

The living area features a blend of classic and modern decor, including a comfortable sofa and elegant armchairs around a richly patterned rug. A brick fireplace adds warmth, while a television is positioned in front of the seating area. Natural light fills the space from large windows.

Apartment in Westport

4.9 out of 5 average rating, 236 reviews

Spacious Westport Apt surrounded by nature!

Spacious mother-in-law basement apartment with private entrance that opens to the backyard. Large windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space for up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, hikes, wonderful bakeries and restaurants.

Guest favorite

A wooden porch is visible, featuring two black chairs and an orange table. Potted flowers add color on either side, with a stone pathway leading into the surrounding greenery. The gray siding of the building complements the outdoor seating area.

Apartment in Redding

4.94 out of 5 average rating, 485 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Time to book your summer getaway or STAYCATION with the Huckleberry Quarters, a beautifully renovated studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy this summer, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

Top guest favorite

A serene view from the covered porch showcases a lush green lawn leading to the tranquil waters of Henderson Pond. Tall trees frame the scene, with dappled sunlight filtering through the leaves, creating a calm and inviting atmosphere.

Guest suite in Wilton

4.9 out of 5 average rating, 146 reviews

Serene Pond Views charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Guest favorite

A charming cottage exterior is surrounded by lush greenery and autumn foliage. The two-story structure features a balcony adorned with potted plants. Large windows create a welcoming appearance, while the grassy area in front offers a peaceful outdoor setting.

Guesthouse in Wilton

4.97 out of 5 average rating, 125 reviews

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed and the living room has a futon couch which folds down. It’s perfect for 1-2 adults, can comfortably fit 3 people if one is a child.

Top guest favorite

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

4.97 out of 5 average rating, 145 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. 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. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Guest favorite

A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.

Guest suite in Wilton

4.81 out of 5 average rating, 190 reviews

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Guest favorite

An open studio space is highlighted by original wooden beams and warm, polished hardwood floors. Multiple skylights provide ample natural light. Furnishings include a comfortable couch, a coffee table, and storage units adorned with artwork, creating a charming, functional atmosphere.

Place to stay in Southport

4.94 out of 5 average rating, 270 reviews

Sunny Westport Studio Apt. Above Historic Mill

Historic Charm Meets Modern Comfort: A Unique Studio Retreat Perched atop a restored 19th-century Cider Mill, this sunlit studio blends timeless character with modern amenities. Enjoy stunning views of a picturesque stream, serene meadows, and diverse wildlife. Just moments from Southport Village, yet offering a peaceful escape, it's perfect for history lovers, business travelers, and design enthusiasts seeking a unique getaway.

Guest favorite

The cottage is surrounded by lush greenery, featuring a charming entrance with a white door and a stone chimney. A greenhouse sits alongside, filled with plants. The front yard is lined with vibrant shrubs and framed by blooming trees under a clear blue sky.

Guesthouse in Wilton

4.98 out of 5 average rating, 46 reviews

The Ciderhouse Cottage - private escape in Wilton

Entirely private cottage on tranquil property. Lovely family friendly space with full kitchen and eat - in dining room. Large living space with french doors that open up to private back yard.Beautiful views of property with private patio & yard. -45 miles to NYC, 1 mile to local metro north train station -5 minutes to downtown Wilton with restaurants/shopping, 10-15 minutes to Westport, New Canaan, Ridgefield

Vacation rentals for every style

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Popular amenities for Weston vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Weston

Top guest favorite

A serene sleeping area is highlighted by a spacious bed dressed in a patterned blanket. Two lamps frame the bedside tables, and a cowhide rug adds texture to the wooden floor. A bright door leads to the entrance, while a small dining table is positioned nearby.

Apartment in Southport

4.85 out of 5 average rating, 73 reviews

Zen studio in Historic Southport Village.

Superhost

A cozy living area features a large blue sectional sofa and a round white coffee table, set against light wooden flooring. A wall-mounted TV displays entertainment options, and natural light streams through sheer curtains, enhancing the inviting ambiance of the space.

Apartment in Bridgeport

5 out of 5 average rating, 4 reviews

Stylish 2King Bed Family Apartment w/no stairs req

Top guest favorite

The exterior of the carriage house is shown, showcasing a charming design with curved garage doors. A spacious lawn features neatly trimmed grass, a decorative planter, and a large tree providing shade in a serene, natural setting.

Chalet in Redding

5 out of 5 average rating, 20 reviews

Enjoy our Connecticut Carriage House

Top guest favorite

The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.

Guesthouse in Waccabuc

4.99 out of 5 average rating, 97 reviews

French Guest House in Waccabuc

Top guest favorite

A spacious living area is furnished with a cozy striped sectional sofa, complemented by a rustic wooden coffee table. Bright natural light filters through the windows, enhancing the neutral decor. Bar stools are arranged at a counter in the background, providing additional seating.

Home in Weston

5 out of 5 average rating, 19 reviews

River Cottage in Weston, CT

Guest favorite

The exterior of the house showcases a charming two-story structure set against a lush green landscape. A tranquil pool reflects the surrounding gardens, while stone steps lead to a welcoming entrance. The area is filled with greenery and outdoor seating, ideal for relaxation.

Home in Redding

4.88 out of 5 average rating, 16 reviews

Meeker Hill House - Country Escape w/ Heated Pool

Top guest favorite

A charming red exterior features white window treatments and a rustic door. Decor elements include a wooden wagon wheel and an artistic iron wall hanging. Lush greenery and flowers are visible in the garden area, enhancing the welcoming entryway.

Guesthouse in Newtown

4.99 out of 5 average rating, 68 reviews

Guest Suite at Wisteria Gardens

Top guest favorite

A two-story house with gray siding and a bright orange front door is framed by well-maintained landscaping. A lamp post stands near the entrance, adding charm to the welcoming facade. The driveway allows for easy access, leading to a garage on the left.

Home in Trumbull

5 out of 5 average rating, 37 reviews

Cozy, updated single family in Fairfield County

Show all

Quick stats about vacation rentals in Weston

Total rentals
60 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

Frequently Asked Questions

Are there pet-friendly vacation rentals in Weston?
Four-legged friends are welcome in Weston. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Weston?
Yes! Work meets play with ease at over 40 vacation rentals in Weston featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Weston have a gym?
Absolutely! We offer over 10 house rentals with a gym in Weston. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Weston have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Weston. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Weston?
Experience the best of Weston with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Weston have wifi?
Absolutely! We offer over 40 house rentals with wifi in Weston. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Weston?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 40 homes with wifi, over 40 homes with air conditioning, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Weston?
Weston has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Weston have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Weston. Enjoy a tailored experience with all the comforts you desire.
Are there Weston vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Weston, available on Airbnb. Make a splash and soak up the sun in style!

Vacation rentals in Weston

Top-rated vacation rentals in Weston

Vacation rentals for every style

Popular amenities for Weston vacation rentals

Other great vacation rentals in Weston

Quick stats about vacation rentals in Weston

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Frequently Asked Questions

Destinations to explore