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

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Weston holiday homes

Living area

1. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is £313
includes taxes & fees
1 Sept - 2 Sept
Gilded Age Luxury Surrounded by Nature
Smart TV

2. 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 £198
includes taxes & fees
31 Aug - 1 Sept
Centric property close to all the great things in the city
Pool

3. 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 £117
includes taxes & fees
22 Sept - 23 Sept
Business or Weekend escape
Private kitchen

4. Elite room stay

Elite room stay
Bridgeport
The price is £257
includes taxes & fees
29 Aug - 30 Aug
Elite room stay
Coffee/tea maker, fridge, microwave, oven

5. 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, (18 reviews)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is £474
includes taxes & fees
30 Aug - 31 Aug
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Beach nearby, sun-loungers, beach towels

6. 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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is £448
includes taxes & fees
21 Sept - 22 Sept
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Smart TV, fireplace, books, stereo

7. 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 £504
includes taxes & fees
30 Aug - 31 Aug
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Coffee/tea maker, fridge, microwave, oven

8. 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 £549
includes taxes & fees
1 Sept - 2 Sept
Spacious Retreat with Game Room and Fire Pit
A heated pool

9. 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 £1,728
includes taxes & fees
7 Sept - 8 Sept
Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability
Interior

10. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."
United States
Raelyn O.
The price is £553
includes taxes & fees
30 Aug - 31 Aug
4 Mi to Beach & Dtwn! Charming Fairfield Home
Coffee/tea maker, fridge, microwave, oven

11. 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 £635
includes taxes & fees
8 Sept - 9 Sept
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Property grounds

12. 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)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is £295
includes taxes & fees
6 Sept - 7 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Dining

13. Renovated Beachside Retreat

Renovated Beachside Retreat
Milford
Renovated Beachside Retreat
Property grounds

14. 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 £295
includes taxes & fees
15 Sept - 16 Sept
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Exterior

15. 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 £931
includes taxes & fees
29 Aug - 30 Aug
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
1 bedroom, iron/ironing board, WiFi, bed sheets

16. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is £359
includes taxes & fees
29 Aug - 30 Aug
Cozy 1-bedroom house in welcoming Bridgeport
Coffee/tea maker, fridge, microwave, oven

17. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is £612
includes taxes & fees
27 Sept - 28 Sept
Renovated Retreat with Heated Pool
TV

18. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is £425
includes taxes & fees
30 Aug - 31 Aug
Spacious Stamford Home | Family, Work, Parking
Interior

19. 5BR Beach House, Water Views, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is £695
includes taxes & fees
1 Sept - 2 Sept
5BR Beach House, Water Views, Game Room, Backyard
TV, books

20. 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 £387
includes taxes & fees
30 Aug - 31 Aug
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
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

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

10/10 Excellent
"I've stayed here multiple times (most recently in August 2026) and am always amazed at how diligent the staff is to keep the lobby and dining area sparkling clean. The housekeeping staff is attentive and responsive, and my entire family uses the gym every time we stay. Highly recommend!"
Kristin 1-night trip
Posted 1 hour ago
Hyatt Place Milford / New Haven

Find out more about Weston

Weston Holiday Homes information

Number of reviews
324
Accommodation
296 Holiday Homes
Lowest Price
£117
Highest Price
£1,728