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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Weston holiday homes

A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

1. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is €382
includes taxes & fees
4 Oct - 5 Oct
Gilded Age Luxury Surrounded by Nature
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

2. 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, (40 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is €533
includes taxes & fees
21 Oct - 22 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

3. 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
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is €239
includes taxes & fees
4 Oct - 5 Oct
Centric property close to all the great things in the city
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

4. 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)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
The price is €528
includes taxes & fees
5 Oct - 6 Oct
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

5. Elite room stay

Elite room stay
Bridgeport
The price is €302
includes taxes & fees
3 Oct - 4 Oct
Elite room stay
A swimming pool at night with blue lighting.

6. 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 €138
includes taxes & fees
6 Oct - 7 Oct
Business or Weekend escape
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

7. 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, (20 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is €320
includes taxes & fees
13 Oct - 14 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Room

8. #37 - Luxury Collection

#37 - Luxury Collection
Stratford
8.4 out of 10, Very good, (5 reviews)
"Peaceful spot, conveniently located."
United States
Katherine
The price is €416
includes taxes & fees
8 Oct - 9 Oct
#37 - Luxury Collection
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

9. 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 €646
includes taxes & fees
28 Oct - 29 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A campfire with a wooden table and benches by a lake.

10. 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)
"Nice stay"
United States
Christopher J.
The price is €283
includes taxes & fees
7 Oct - 8 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A bedroom with a bed, two bedside tables, a lamp, an air conditioning unit, a patterned rug, and a painting on the wall.

11. Renovated Beachside Retreat

Renovated Beachside Retreat
Milford
The price is €318
includes taxes & fees
8 Oct - 9 Oct
Renovated Beachside Retreat
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

12. 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 €820
includes taxes & fees
4 Oct - 5 Oct
4 Mi to Beach & Dtwn! Charming Fairfield Home
A modern kitchen with white cabinets, a marble island, and black bar stools.

13. 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 €760
includes taxes & fees
28 Oct - 29 Oct
Spacious Retreat with Game Room and Fire Pit
A living room with a sofa set, a coffee table, and a television on a stand.

14. 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 €520
includes taxes & fees
5 Oct - 6 Oct
Spacious Stamford Home | Family, Work, Parking
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

15. 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 €633
includes taxes & fees
4 Oct - 5 Oct
Renovated Retreat with Heated Pool
A two-story house with a porch, stone steps, and a variety of plants.

16. 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 €1,142
includes taxes & fees
5 Oct - 6 Oct
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A bedroom with two beds, a wooden dresser, and a mirror.

17. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is €432
includes taxes & fees
3 Oct - 4 Oct
Cozy 1-bedroom house in welcoming Bridgeport
A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

18. 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 €429
includes taxes & fees
4 Oct - 5 Oct
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

19. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is €1,365
includes taxes & fees
6 Oct - 7 Oct
Beechmont - Perfect for Family Retreat!
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

20. 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 €716
includes taxes & fees
5 Oct - 6 Oct
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Nice clean hotel and wonderful staff."
Michael 1-night trip
Posted 1 hour ago
Best Western Executive Hotel Of New Haven - West Haven

Find out more about Weston

Weston Holiday Homes information

Number of reviews
246
Accommodation
294 Holiday Homes
Lowest Price
€138
Highest Price
€1,365