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 AU$610
includes taxes & fees
29 Sept - 30 Sept
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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is AU$809
includes taxes & fees
30 Sept - 1 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

3. 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 AU$920
includes taxes & fees
6 Oct - 7 Oct
Renovated Cape Near beach, with Fire Pit and BBQ, 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.

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
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is AU$379
includes taxes & fees
4 Oct - 5 Oct
Centric property close to all the great things in the city
A swimming pool at night with blue lighting.

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 AU$220
includes taxes & fees
4 Oct - 5 Oct
Business or Weekend escape
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

6. Elite room stay

Elite room stay
Bridgeport
The price is AU$487
includes taxes & fees
29 Sept - 30 Sept
Elite room stay
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

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 AU$985
includes taxes & fees
19 Oct - 20 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

8. 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, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is AU$467
includes taxes & fees
30 Sept - 1 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A campfire with a wooden table and benches by a lake.

9. 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 AU$443
includes taxes & fees
5 Oct - 6 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

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 AU$1,060
includes taxes & fees
11 Oct - 12 Oct
4 Mi to Beach & Dtwn! Charming Fairfield Home
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

11. 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 AU$1,011
includes taxes & fees
25 Oct - 26 Oct
Renovated Retreat with Heated Pool
A modern kitchen with white cabinets, a marble island, and black bar stools.

12. 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 AU$1,076
includes taxes & fees
28 Oct - 29 Oct
Spacious Retreat with Game Room and Fire Pit
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.

13. 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 AU$650
includes taxes & fees
1 Oct - 2 Oct
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A two-story house with a porch, stone steps, and a variety of plants.

14. 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 AU$1,771
includes taxes & fees
29 Sept - 30 Sept
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

15. 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 AU$1,416
includes taxes & fees
5 Oct - 6 Oct
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A bedroom with two beds, a wooden dresser, and a mirror.

16. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is AU$675
includes taxes & fees
29 Sept - 30 Sept
Cozy 1-bedroom house in welcoming Bridgeport
A living room with a sofa set, a coffee table, and a television on a stand.

17. 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 AU$797
includes taxes & fees
29 Sept - 30 Sept
Spacious Stamford Home | Family, Work, Parking
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

18. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
The price is AU$943
includes taxes & fees
30 Sept - 1 Oct
5BR Beach Home | Walk to Cove Beach + Private Yard
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 AU$2,259
includes taxes & fees
29 Sept - 30 Sept
Beechmont - Perfect for Family Retreat!
A living room with a staircase, a sofa, a coffee table, and a TV.

20. Loft •Pool • Gym • Free Parking • Near Yale

Loft •Pool • Gym • Free Parking • Near Yale
Orange
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. Host was accommodating and quick to respond when we encountered issues."
United States
Ali B.
The price is AU$380
includes taxes & fees
29 Sept - 30 Sept
Loft •Pool • Gym • Free Parking • Near Yale
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 Regency Greenwich

Hyatt Regency Greenwich

8/10 Good
"The hotel was very clean and spacious. Even though there were several large events going on while we were there, there was ample parking, space to relax and no lack in service. It never felt crowded or excessively noisy. We did not use the gym but it was very well organized and clean with working equipment. We did use the pool every day. I do think for the price there should have been a complimentary breakfast and coffee bar. They could have offered a discount at the small coffee shop in the lobby. Unfortunately when our son and his children arrived the room they were given was completely unmade. They had to be relocated to another room. I would recommend this hotel to others."
Marc 4-night trip
Posted 1 hour ago
Hyatt Regency Greenwich

Find out more about Weston

Weston Holiday Homes information

Number of reviews
267
Accommodation
294 Holiday Homes
Lowest Price
AU$220
Highest Price
AU$2,259