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Compare 375 Vacation Homes in Weston with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (6)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (19)
"This is a beautiful property. When we arrived, everything was perfect. It is completely stocked, including games for the family, and an unbelievable view of the lake. Communication with the homeowner was wonderful and we definitely plan to come back. We highly recommend this beautiful, clean and well kept home on the lake!."
Lakeside luxury: beautiful, relaxing 4 bedroom home

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (106)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Business or Weekend escape

9.4 out of 10, Exceptional, (33)
"We had a wonderful stay here. It was the perfect man cave for a mom and two teenage boys! It was very clean and the host was amazing! He was very very helpful with questions we had and things that we needed in the area. I would definitely stay with him again."
The price is AED 275
AED 496 total
includes taxes & fees
30 Mar - 31 Mar
Business or Weekend escape

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (29)
"We had 8 people staying in the house. We were in town for a wedding. The house was well fitted for us. Kitchen had all the dishes we needed. Appliances all worked well. Nice walk to the sound. Neighborhood was kind of iffy but we had no problems. "
Cheerful 4 bedrooms residential house.

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

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"House is absolutely perfect! This is our second time staying and we will definitely return. So much charm and warmth. I had the best sleep that I have had in months. All the amenities you could ask for, and more. Terrific convenient location. Host goes above and beyond to make sure we are comfortable. "
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (27)
"We loved the location and the space was great for our visit. Very clean and cozy. Would recommend and we would book again if we are ever back in the area. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (116)
"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"The home was spacious and provided recreation for kids with hot tub, gym, ping pong, foosball, and game. However, property was advertised as 9 bedrooms and 7 baths. My family looked forward to spreading out but 4 bedrooms with adjoining bathrooms were locked. Text host to see if he would open them but he declined. That was disappointing."
Over Sized Colonial on Private Road.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"Great home with fun ping pong table!"
The price is AED 2,031
AED 3,753 total
includes taxes & fees
13 Apr - 14 Apr
New Beach Home near Stamford Downtown/Shippan

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.4 out of 10, Exceptional, (10)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Ocean Front Beach House with Private Beach Access - Newly Renovated!

10.0 out of 10, Exceptional, (14)
"Communication was top notchThe property was very well appointed and perfect for a family gathering The most important part was the accessibility of the bathroom and bedroom for my mom who has mobility issues I was worried about the half step from bedroom to bathroom but I put pick lights on floor to remind her to step upLocation was perfect Especially loved visiting pez!"
Ocean Front Beach House with Private Beach Access - Newly Renovated!

Cottage at Sunny Day- Lakeside, views, kayak, dock

9.8 out of 10, Exceptional, (35)
"This property was very new and clean. It had everything you needed. Every room was comfortable and had its own TV. The open layout of the main floor made for great socializing and eating, and the 180 views of the frozen lake (in February) were beautifully serene. Would definitely come again and maybe next time in the summer! Thanks you for sharing this lovely property."
Cottage at Sunny Day- Lakeside, views, kayak, dock

Waterfront Family Retreat on Candlewood Lake

10.0 out of 10, Exceptional, (41)
"The Hosts were extremely nice and helpful in the entire process. They answered questions and helped me understand the offering so I could book with confidence, The home is spacious and welcoming in design. Generous spaces throughout including a very nice kitchen and a basement gameroom that was very enjoyable. The outside seating areas were outstanding including a wonderful lakefront area to sit and enjoy the views. Book with confidence for a great experience. Dan and Kit "
Waterfront Family Retreat on Candlewood Lake

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Westport Gem - walk to shops, dining, town center, pet-friendly

Spacious 4-bedroom house with WiFi and AC in awesome Milford

The price is AED 1,300
AED 2,630 total
includes taxes & fees
30 Mar - 31 Mar
Spacious 4-bedroom house with WiFi and AC in awesome Milford

NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

10.0 out of 10, Exceptional, (5)
"This place is amazing!! The house had everything we needed and more. We really enjoyed our stay and also be able to host some of our family in the area was precious. My daughters rented equipment for the babies which worked out well. The house is very spacious and 5 adults and 3 children fit nicely. Very highly recommend. The pier was fun to hang out on but due to weather we were to enjoy the lake as much. Easy to find, and owners were very responsive. "
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

Charming West Haven Home - Walk to Beach!

8.6 out of 10, Excellent, (11)
"Clean house in a convenient and quiet location. Close to many store and restaurants. House was well equipped. Sauna was a nice extra. Only complaints are that the bed in the third bedroom is not for adults and the towels need to be replaced. We would definitely rent the house again when in the area. "
Charming West Haven Home - Walk to Beach!
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

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (49)
"Really liked Dune. I had a great room that was on the other side from Sea Grape - bar that could be loud. I heard noting from room 31. Could walk to Post Rd and the beach. Ocean view from room. "
The price is AED 1,003
AED 1,525 total
includes taxes & fees
5 Apr - 6 Apr
DUNE Fairfield Beach

Stamford Suites

3.0 star property
7.0 out of 10, Good, (386)
"Room was very spacious "
The price is AED 585
AED 673 total
includes taxes & fees
30 Mar - 31 Mar
Stamford Suites

Business or Weekend escape

9.4 out of 10, Exceptional, (33)
"We had a wonderful stay here. It was the perfect man cave for a mom and two teenage boys! It was very clean and the host was amazing! He was very very helpful with questions we had and things that we needed in the area. I would definitely stay with him again."
The price is AED 275
AED 496 total
includes taxes & fees
30 Mar - 31 Mar
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.