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 50 vacation rentals in Weston featuring dedicated workspaces. Stay connected and productive in your home away from home.

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 40 homes with air conditioning, over 30 homes with a kitchen, over 40 homes with wifi, over 40 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Do house rentals in Weston have free parking?

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

Where should I stay in Weston?

Make yourself at home in Weston by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in Cannondale, and over 140 vacation rentals in Wilton Center.

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 kitchen?

Absolutely! We offer over 30 house rentals with a kitchen in Weston. Enjoy a tailored experience with all the comforts you desire.

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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Top guest favorite

The spacious living area features a large window allowing natural light to fill the room. A comfortable seating arrangement includes a plush armchair and a sofa, accompanied by a coffee table. Decorative plants and a decorative rug complement the elegant furnishings, including a classic wooden armoire.

Guest suite in Fairfield

4.95 out of 5 average rating, 220 reviews

2 BRm Suite; Ktchn; Livng area; wash/dryr; Private

Fully accessorized, large (919 sq ft) beautiful suburban space with bedroom (queen); convertible Murphy bed (queen), in-room sitting area/large screen TV, kitchenette; 2nd room: bedroom (queen) with living space / large screen TV; private full bath; in-suite washer/dryer; private entry to suite (front door; up 1 flight of stairs). Includes light continental breakfast. Owners on property. Off street parking. Train station a mile away (NYC: 70 min). 2 miles to beach. Easy walk to Fairfield U.

Top 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, 252 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.

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

4.91 out of 5 average rating, 154 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 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, 488 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

It’s time to book your FALL LEAF-PEEPING sojourn at 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 FALL, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

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, 132 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, 166 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

Superhost

The Solar Cabin is nestled among lush greenery, featuring a rustic wooden exterior with a metal roof. Large windows allow natural light to fill the space, while a stone pathway leads to the entrance. Surrounding foliage enhances the cabin's secluded ambience.

Cabin in Newtown

4.89 out of 5 average rating, 122 reviews

Sticks and Stones Farm - The Solar Cabin

Sticks and Stones Farm offers a rustic glamping experience! When you stay with us you'll get the adventure and fun of camping (no electricity, outdoor showers etc.) while still getting to lay your head on a soft pillow in a bed. You can treat your stay here as a chance to go inward or enjoy interacting with the different programs and events going on! If you want to be up to date on events or ask about weekday checkins you can message us directly.

Guest favorite

A living room scene is displayed with a comfortable gray sofa and an accent chair positioned around a light wood coffee table. A fireplace is centered against a white brick wall, featuring a warm fire. A flat-screen TV is mounted above the mantel.

Home in Fairfield

4.96 out of 5 average rating, 162 reviews

Top Rated Gem | Fire Pit | BBQ | FFU | Near Beach

Welcome to Fairfield Cottage, a cozy retreat that beautifully combines comfort and stylish design for you and your guests. With thoughtful decor and essential amenities, you'll feel right at home. Conveniently located just 90 minutes to NYC, you can easily visit attractions like the Norwalk Aquarium, Beardsley Zoo, and local farms. Unwind at nearby Jennings and Penfield beaches located just 3 miles away, or explore the charming village of Southport.

Superhost

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

4.8 out of 5 average rating, 220 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.

Top guest favorite

The bedroom features a queen size spindle bed with quality bedding, flanked by two nightstands with lamps. A dedicated work desk is equipped with a lamp and USB ports. Shelving adds storage, while a small seating area is present, illuminated by natural light from the windows.

Apartment in Fairfield

4.97 out of 5 average rating, 146 reviews

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

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

4.93 out of 5 average rating, 274 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.

Top guest favorite

A comfortable outdoor seating area features two wooden lounge chairs beneath a yellow umbrella, overlooking a gentle cascade of water. Lush greenery surrounds the space, enhancing the serene atmosphere, while the sound of the flowing brook adds to the tranquil experience.

Cabin in Redding

4.99 out of 5 average rating, 104 reviews

The Zen Cabin

Seated beside a playful cascade on Moffit’s Brook, this 1960 Log Cabin has been mindfully rejuvenated. 62 miles from NYC, The Zen Cabin offers respite from the hustle and bustle. Skylights, windows, and doors connect you with nature. Media-free, pet-free, and shoe-free. This laid-back retreat resides in one of Connecticut’s most bucolic and protected villages.

Vacation rentals for every style

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Unique stays

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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 cozy living area is highlighted by large windows allowing natural light to fill the space. A comfortable couch faces a wooden coffee table, complemented by a patterned rug beneath. A potted plant adds a touch of greenery, while a mirror reflects the room's brightness.

Guest suite in Weston

5 out of 5 average rating, 46 reviews

Cozy, Fall Retreat Private Suite 5 Min to Westport

Guest favorite

A modern kitchen area is highlighted by clean white cabinetry and a warm wooden island. A decorative plant sits atop the island, alongside a lit candle. Soft lighting from pendant fixtures creates a cozy ambiance, while stainless steel appliances complement the space.

Apartment in Weston

4.95 out of 5 average rating, 19 reviews

Relaxing studio in woods nearby everything

Top guest favorite

The exterior of the home is showcased during sunset, with buildings featuring modern architectural lines. A landscaped yard with gravel pathways and trees creates a serene environment. Warm sunlight casts a golden hue, enhancing the inviting ambiance of the property.

Home in Westport

5 out of 5 average rating, 68 reviews

Westport: Deco HAUS 5 min to Town /10 min to Beach

Top guest favorite

The exterior of a newly renovated cottage is showcased, with a sloped roof and a light-colored façade. Neatly trimmed shrubs and grass create a welcoming entrance, complemented by a stone pathway leading to the front door. A few trees provide greenery against a bright blue sky.

Cottage in Westport

5 out of 5 average rating, 71 reviews

Wild Rose Cottage (Westport, CT)

Guest favorite

The spacious kitchen features white cabinetry and dark granite countertops. A central island with seating for two is present. Large windows provide ample natural light and views of the outdoor greenery. Appliances include a microwave, stove, and dishwasher, contributing to a fully equipped cooking space.

Home in Westport

5 out of 5 average rating, 25 reviews

Westport Gem - walk to shops, dining, town center

Guest favorite

The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.

Guesthouse in Pound Ridge

4.94 out of 5 average rating, 96 reviews

A Lovely Cottage in the Woods with Private 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, 90 reviews

Guest Suite at Wisteria Gardens

Superhost

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

4.94 out of 5 average rating, 47 reviews

The Ciderhouse Cottage - private escape in Wilton

Quick stats about vacation rentals in Weston

Total rentals
60 properties
Nightly prices starting at
G$8,369 GYD 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 50 vacation rentals in Weston featuring dedicated workspaces. Stay connected and productive in your home away from home.
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 40 homes with air conditioning, over 30 homes with a kitchen, over 40 homes with wifi, over 40 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Weston have free parking?
Absolutely! We offer over 40 house rentals with free parking in Weston. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Weston?
Make yourself at home in Weston by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in Cannondale, and over 140 vacation rentals in Wilton Center.
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 kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Weston. Enjoy a tailored experience with all the comforts you desire.

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