A calm lake surrounded by dense forest and a cloudy sky.

Holiday Homes in Weston

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Weston holiday homes

Exterior

1. Dream Vacation Home

Dream Vacation Home
Derby
10.0 out of 10, Exceptional, (1 review)
"."
United States
shannon
The price is €178
includes taxes & fees
21 Aug - 22 Aug
Dream Vacation Home
Dining

2. Renovated Beachside Retreat

Renovated Beachside Retreat
Milford
The price is €403
includes taxes & fees
18 Aug - 19 Aug
Renovated Beachside Retreat
Living area

3. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is €365
includes taxes & fees
14 Sept - 15 Sept
Gilded Age Luxury Surrounded by Nature
Smart TV

4. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.8 out of 10, (16 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is €234
includes taxes & fees
18 Aug - 19 Aug
Centric property close to all the great things in the city
Pool

5. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is €136
includes taxes & fees
7 Sept - 8 Sept
Business or Weekend escape
Private kitchen

6. Elite room stay

Elite room stay
Bridgeport
The price is €303
includes taxes & fees
18 Aug - 19 Aug
Elite room stay
Private kitchen

7. Spacious Family Home

Spacious Family Home
Westport
10.0 out of 10, Exceptional, (1 review)
"We had a getaway weekend for a close friend group from college. This location could not have been better! We had everything we needed. Four bedrooms and three full bathrooms and across the street, a bakery, pizza place, fantastically stocked market, and a nice restaurant! A short drive allowed us to enjoy shopping and more food choices, as well as giving our Manhattan friend easy access to the train. Really could not have been a better place for us. Communication with the host was timely,...
United States
Laura B.
The price is €790
includes taxes & fees
25 Aug - 26 Aug
Spacious Family Home
Beach nearby, sun-loungers, beach towels

8. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (38 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is €592
includes taxes & fees
14 Sept - 15 Sept
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Coffee/tea maker, fridge, microwave, oven

9. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (17 reviews)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is €571
includes taxes & fees
16 Sept - 17 Sept
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Smart TV, fireplace, books, stereo

10. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
The price is €661
includes taxes & fees
23 Aug - 24 Aug
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Coffee/tea maker, fridge, microwave, oven

11. 5 minute walk to beach, walk to town & train

5 minute walk to beach, walk to town & train
Fairfield Beach
10.0 out of 10, Exceptional, (26 reviews)
"Host was great. Had a great stay. "
United States
jeff d.
The price is €813
includes taxes & fees
23 Aug - 24 Aug
5 minute walk to beach, walk to town & train
A heated pool

12. Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability

Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability
New Canaan
10.0 out of 10, Exceptional, (42 reviews)
"Unique home with beautiful grounds and classically designed interior. Perfect for relaxing and enjoying with family/friends."
United States
David
The price is €1,880
includes taxes & fees
7 Sept - 8 Sept
Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability
Coffee/tea maker, fridge, microwave, oven

13. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.4 out of 10, Exceptional, (20 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
The price is €720
includes taxes & fees
8 Sept - 9 Sept
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Coffee/tea maker, fridge, microwave, oven

14. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, Exceptional, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
The price is €640
includes taxes & fees
16 Sept - 17 Sept
Spacious Retreat with Game Room and Fire Pit
Property grounds

15. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (18 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is €318
includes taxes & fees
15 Sept - 16 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
TV, books

16. Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is €423
includes taxes & fees
18 Aug - 19 Aug
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Front of property

17. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is €1,112
includes taxes & fees
18 Aug - 19 Aug
Beechmont - Perfect for Family Retreat!
Property grounds

18. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (42 reviews)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
The price is €327
includes taxes & fees
15 Sept - 16 Sept
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
1 bedroom, iron/ironing board, WiFi, bed sheets

19. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is €423
includes taxes & fees
18 Aug - 19 Aug
Cozy 1-bedroom house in welcoming Bridgeport
Exterior

20. Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
8.8 out of 10, Excellent, (10 reviews)
"Plenty of bedrooms and space for the family. Very prompt communication with host."
United States
David K.
The price is €1,092
includes taxes & fees
25 Aug - 26 Aug
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
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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Top Weston Hotel Reviews

Red Roof Inn Milford - New Haven

Red Roof Inn Milford - New Haven

8/10 Good
"A good value for what I paid overall. I was pleased with my stay Pros: The staff were all professional and nice The TV simple and easy to use which I really appreciated I loved having a fridge and a freezer in the room. That was so great It felt clean overall. It did seem like housekeeping put effort into making the room nice (that was the energy I felt) I liked that it did not smell like a bunch of cleaning chemicals in the room which some hotels real of The layout of the room was functional I appreciated the signage that made it very clear no smoking is allowed at all as that helps me feel more comfortable in hotels Cons: The tub had paint peeling off of it The tub had no stopper, so I went and purchased my own to be able to use it The bathroom door had a stain on it that was a bit of an eye sore and did not seem the most sanitary but I tried to ignore it The tub water was scalding hot and could have been really dangerous. It took a while to find the right temperature The safe in my room was broken so I could not use it"
Patricia 2-night trip
Posted 8 hours ago
Red Roof Inn Milford - New Haven

Find out more about Weston

Weston Holiday Homes information

Number of reviews
307
Accommodation
329 Holiday Homes
Lowest Price
€136
Highest Price
€1,880