
Holiday rentals in Weston
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Weston
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Family Cottage with 4 King Beds and Fire Pit
Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.

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…

Huckleberry Quarters, the Cozy Redding Retreat.
Now is the time to book your SPRING STAYCATION at the Huckleberry Quarters, a beautifully appointed 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 any season, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

The Cozy Little Cottage
Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our 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. We have a twin air mattress for use in the living room.

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

The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

A Lovely Cottage in the Woods
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

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.

French Guest House in Waccabuc
A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

Fern Grove Cottage
If you’re looking for tranquility, this is the place for you! This charming cottage is located on a secluded country road. The cottage sits at the back of a gorgeous park-like property, and is near parks with hiking trails. This antique cottage has many modern renovations, providing convenience and comfort while maintaining the historic charm. This is the perfect getaway!

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.
Popular amenities for Weston holiday rentals
Stay near Weston's top sights
Other great holiday rentals in Weston

Brook Haven Home away from home!

Fully Renovated Rural Barn

Historic Designer City Getaway

Designer Treehouse with Spa Bath

Peaceful New Canaan 2-BdRm Cottage - Pet Friendly!

Enjoy our Connecticut Carriage House

Convenient and Cozy Antique Cape

Delightfully Renovated Colonial Barn by the Beach!
When is the best time to visit Weston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $179 SGD | $174 SGD | $189 SGD | $189 SGD | $346 SGD | $359 SGD | $461 SGD | $380 SGD | $218 SGD | $299 SGD | $207 SGD | $218 SGD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
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.
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.
Are there pet-friendly vacation rentals in Weston?
Four-legged friends are welcome in Weston. Choose from more than 30 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.
Are there Weston house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Weston, available on Airbnb. Make a splash and soak up the sun in style!
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 160 vacation rentals in Wilton Center.
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.
Do house rentals in Weston have a kitchen?
Absolutely! We offer over 40 house rentals with a kitchen in Weston. Enjoy a tailored experience with all the comforts you desire.
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.
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.
Quick stats about holiday rentals in Weston

Total holiday rentals
Explore 60 holiday rentals in Weston

Nightly prices starting at
Weston holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 1,350 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
60 of Weston holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Weston rentals

4.9 Average rating
Weston stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Times Square
- Madison Square Garden
- New York City Center
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Yale University
- Bronx Zoo
- Brooklyn Bridge
- Yankee Stadium
- Rockefeller Center
- United Nations Headquarters
- Jones Beach
- Empire State Building
- Citi Field
- Grand Central Terminal
- Bryant Park
- Radio City Music Hall
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Thunder Ridge Ski Area
- The Metropolitan Museum of Art
- Fairfield Beach
- Ohel Chabad-Lubavitch




