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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 299 Vacation Homes in Weston with updated reviews, rates, and availability.

Cozy Ocean Front Retreat with Private Beach!
Room

Cozy Ocean Front Retreat with Private Beach!

10.0 out of 10, Exceptional, (16)
"The views from this home are great - really enjoyed sunrises from the master bedroom. A very comfortable home with everything we needed. "
Cozy Ocean Front Retreat with Private Beach!
Escape to a Celebrity Chef's Waterfront Lake House

Escape to a Celebrity Chef's Waterfront Lake House

Escape to a Celebrity Chef's Waterfront Lake House
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (82)
"Was amazing from beginning to end. From ease of booking to a wonderful stay. Lovely house and we felt very much at home. "
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
View of the front and outside of house with driveway and garage.

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (93)
"Dierdre's home was a perfect spot for our family Thanksgiving. Well located, well stocked, and very well cared for!"
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Terrace/patio

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

10.0 out of 10, Exceptional, (16)
"My time spent at the lake house with my family was unforgettable. Nestled along the serene shoreline, the house offered stunning lake views from every window. Mornings began with coffee on the spacious deck, watching the sun rise over the water. Days were filled with family fun. The house itself was cozy yet modern, with plush furnishings, a crackling fireplace, and a fully-equipped kitchen where we cooked meals together. Evenings were spent playing board games, hanging out by the fire pit. It...
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Bright Milford Beach House w/ Outdoor Shower
Milford Vacation Rental | 2BR | 2.5BA | Stairs Required | 1,450 Sq Ft

Bright Milford Beach House w/ Outdoor Shower

9.6 out of 10, Exceptional, (7)
"We had the best time! It was clean, good location, and the owner was wonderful! We even got to go the beach in December! We would definitely rent this place again!!"
Bright Milford Beach House w/ Outdoor Shower
Historic Hideaway with Lake Access!
Living area

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (13)
"We had a great stay at this fascinating historic house! The house is exactly as described and the hosts were incredibly responsive, even to a last minute request to extend our stay."
Historic Hideaway with Lake Access!
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Terrace/patio

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Exterior

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (28)
"Our family's stay at Helen and Richie's property for the holidays was perfect. Waking up to views of the lake every morning, watching flocks of birds travel on the water and being surrounded by nature was all we could ask for. The house has all amenities provided in the kitchen, bathrooms etc. Location is convenient near shops, grocery, and restaurants in New Fairfield. The hosts were very responsive in communication and I appreciated them providing everything we needed. "
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Dining

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Cheerful 4 bedrooms residential house.
Exterior

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (26)
"The house was clean, comfortable, and kitchen was great. Only problem was stairs for my handicapped sister-too steep but possible. Manager very nice"
Cheerful 4 bedrooms residential house.
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Interior

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Cottage at Sunny Day, multiple levels for multiple views of the lake

Stay 3 Nights or Longer Until January 31 and Get 15% Off

9.8 out of 10, Exceptional, (30)
"A lovely place but a lot of stairs - there is a broken stair lift for the upstairs bedroom - no bathroom on the main floor so for anyone with knee etc issues, this is not the place to stay- beautiful home and location - fully equipped kitchen and comfortable stay otherwise - perfect for warmer months with lake activities"
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (25)
"Great place, great service!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway
Waterview House Walking Distance from Cove Beach
Sunbathing lounge chairs

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (18)
"This was a late holiday gathering of family members from St. Louis and Rye New York. Great and easy spot to get to. Pretty setting with the water view. I am sure in warmer seasons it be great spot for all the outside amenities. Six adults and one baby. Space nice set up. "
The price is AED 2,935
AED 5,071 total
includes taxes & fees
14 Feb - 15 Feb
Waterview House Walking Distance from Cove Beach
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Breathtaking lake views while grilling out and soaking up the sun with family!

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (18)
"We had a friend group boardgaming weekend and this was perfect for our purposes. The table was large enough for our biggest games and the pool table doubled as a backup playing space. The race cars are a nice touch of whimsy too :-) Our only suggestion would be to replace the oversized, too-low chandelier over the table but really only a minor thing."
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Traveling Nurse or Business Professional
Exterior

Traveling Nurse or Business Professional

10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
New Beach Home near Stamford Downtown/Shippan
Open concept living/dining room

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (18)
"We were 9 adult women. There was plenty of space for us to gather as a group as well as sleep. The house is clean and in a great neighborhood. Very easy on and off to the highway to get to our conference in Darien. Highly recommend."
The price is AED 1,315
AED 2,991 total
includes taxes & fees
28 Jan - 29 Jan
New Beach Home near Stamford Downtown/Shippan
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed, Near...
Living area

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed, Near...

9.2 out of 10, Wonderful, (5)
"It’s nice to have a place for our family of 5 that actually fits us all. Plenty of space and very clean. Thanks "
The price is AED 691
AED 1,613 total
includes taxes & fees
25 Jan - 26 Jan
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed, Near...
Entire House on Scenic Estate with Private Pond in Exclusive Neighborhood
The Pond House

Entire House on Scenic Estate with Private Pond in Exclusive Neighborhood

9.8 out of 10, Exceptional, (12)
"The property is beautiful and relaxing! We had everything we needed for a great Thanksgiving. Gustavo was an excellent host who checked in on us for anything we might need. I highly recommend this rental! The pond view is stunning and we had 4 ducks visit. "
Entire House on Scenic Estate with Private Pond in Exclusive Neighborhood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Weston

Adorable 1-Bedroom Cottage in Weston, CT
Living-Room view from Mezzanine

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (36)
"Enjoyed our stay. Jacques is probably the most responsive owner I have ever rented from. Makes a real difference. Always helpful with any queries. "
The price is AED 716
AED 1,099 total
includes taxes & fees
24 Jan - 25 Jan
Adorable 1-Bedroom Cottage in Weston, CT
Stamford Suites
Exterior

Stamford Suites

3.0 star property
6.8 out of 10, (773)
"It was in walking distance of the event we were going to."
The price is AED 506
AED 582 total
includes taxes & fees
3 Feb - 4 Feb
Stamford Suites
Business or Weekend escape
A Queen Size Bed for Two Persons and Also Queen Size Sofa Bed for Two Persons.

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is AED 275
AED 496 total
includes taxes & fees
26 Jan - 27 Jan
Business or Weekend escape
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.