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

Holiday Homes in Weston

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Our top choices for Weston holiday homes

1. 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, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is NZ$1,025
includes taxes & fees
9 Nov - 10 Nov
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

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, (18 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is NZ$451
includes taxes & fees
5 Nov - 6 Nov
Centric property close to all the great things in the city

3. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is NZ$979
includes taxes & fees
5 Nov - 6 Nov
Gilded Age Luxury Surrounded by Nature

4. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is NZ$256
includes taxes & fees
5 Nov - 6 Nov
Business or Weekend escape

5. 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, (16 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 NZ$1,084
includes taxes & fees
5 Nov - 6 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

6. 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, (19 reviews)
"Beautiful home, clean and exactly as described.We loved our stay and plan on returning.The host was wonderful to work with.An overall excellent experience."
United States
Tara C.
The price is NZ$1,054
includes taxes & fees
9 Nov - 10 Nov
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

7. Elite room stay

Elite room stay
Bridgeport
The price is NZ$582
includes taxes & fees
5 Nov - 6 Nov
Elite room stay

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

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.6 out of 10, Exceptional, (21 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 NZ$1,361
includes taxes & fees
9 Nov - 10 Nov
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

9. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay."
United States
Linda S.
The price is NZ$1,192
includes taxes & fees
8 Nov - 9 Nov
Spacious Retreat with Game Room and Fire Pit

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

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
6.0 out of 10, (2 reviews)
"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 NZ$1,559
includes taxes & fees
5 Nov - 6 Nov
4 Mi to Beach & Dtwn! Charming Fairfield Home

11. 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 NZ$2,193
includes taxes & fees
9 Nov - 10 Nov
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

12. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is NZ$1,306
includes taxes & fees
18 Nov - 19 Nov
Renovated Retreat with Heated Pool

13. 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, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is NZ$590
includes taxes & fees
5 Nov - 6 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

14. Stamford Home | Family, Work and Plenty of Parking

Stamford Home | Family, Work and Plenty of 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 NZ$794
includes taxes & fees
9 Nov - 10 Nov
Stamford Home | Family, Work and Plenty of Parking

15. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (21 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is NZ$779
includes taxes & fees
5 Nov - 6 Nov
Gem by the water+ firepit and all fenced backyard

16. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NZ$1,899
includes taxes & fees
4 Dec - 5 Dec
Beechmont - Perfect for Family Retreat!

17. 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 NZ$801
includes taxes & fees
9 Nov - 10 Nov
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

18. Spacious 3BR Townhome | Garage + Near Downtown

Spacious 3BR Townhome | Garage + Near Downtown
West Side
9.2 out of 10, Wonderful, (9 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is NZ$1,075
includes taxes & fees
5 Nov - 6 Nov
Spacious 3BR Townhome | Garage + Near Downtown

19. 5BR Beach House, Water Views, Steps to Beach, Backyard

5BR Beach House, Water Views, Steps to Beach, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (32 reviews)
"The property was amazing. The house was clean, beautiful, and well equipped. Plenty of space yet still cozy. Host was very communicative and gracious, had a pleasant experience and will definitely be back!"
United States
Maxx V.
The price is NZ$2,034
includes taxes & fees
11 Nov - 12 Nov
5BR Beach House, Water Views, Steps to Beach, Backyard

20. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is NZ$802
includes taxes & fees
5 Nov - 6 Nov
Cozy 1-bedroom house in welcoming Bridgeport
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

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Weston Holiday Homes information

Number of reviews
276
Accommodation
283 Holiday Homes
Lowest Price
NZ$256
Highest Price
NZ$2,193