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

Search Holiday Homes in Weston

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Weston holiday homes

A luxurious living room with a tufted sofa, a glass coffee table with decorative items, and a floral arrangement.

1. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is £322
includes taxes & fees
20 Oct - 21 Oct
Gilded Age Luxury Surrounded by Nature
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

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
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is £205
includes taxes & fees
20 Oct - 21 Oct
Centric property close to all the great things in the city
A swimming pool at night with blue lighting.

3. 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 £118
includes taxes & fees
17 Oct - 18 Oct
Business or Weekend escape
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

4. 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)
The price is £444
includes taxes & fees
3 Nov - 4 Nov
Cozy Cottage with Fire Pit, near Beach, 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 £262
includes taxes & fees
17 Oct - 18 Oct
Elite room stay
Deck: Comfortable outdoor sofa sets for outdoor conversations

6. Serenity Haven: A Modern Retreat

Serenity Haven: A Modern Retreat
Monroe
9.6 out of 10, Exceptional, (5 reviews)
"My stay at the modern retreat in Monroe was perfect. Conveniently located near restaurants, supermarkets, banks Starbucks. Beautiful Wolfe Park is minutes away to enjoy a hike or a bike ride.The hosts were easily accessible with any questions and or concerns.This modern retreat won't disappoint."
United States
Tresha J.
Serenity Haven: A Modern Retreat
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

7. 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 £458
includes taxes & fees
15 Oct - 16 Oct
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

8. 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 £515
includes taxes & fees
9 Nov - 10 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

9. 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 £595
includes taxes & fees
21 Oct - 22 Oct
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A modern kitchen with white cabinets, a marble island, and black bar stools.

10. 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 £584
includes taxes & fees
5 Nov - 6 Nov
Spacious Retreat with Game Room and Fire Pit
A white room with a round table, two benches, and a window with a view of houses.

11. Stay at Black Rock Harbor

Stay at Black Rock Harbor
Black Rock Historic District
10.0 out of 10, Exceptional, (29 reviews)
"This house was perfect for our family. Will definitely use again when we're visiting family in the area."
United States
Laura L.
The price is £725
includes taxes & fees
1 Nov - 2 Nov
Stay at Black Rock Harbor
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 £699
includes taxes & fees
19 Oct - 20 Oct
4 Mi to Beach & Dtwn! Charming Fairfield Home
A two-story house with a porch, stone steps, and a variety of plants.

13. 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 £977
includes taxes & fees
20 Oct - 21 Oct
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

14. 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 £561
includes taxes & fees
11 Nov - 12 Nov
Renovated Retreat with Heated Pool
A living room with a sofa, a coffee table, a flat-screen TV, a wooden cabinet, and a clock on the wall.

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)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is £262
includes taxes & fees
10 Nov - 11 Nov
Gem by the water+ firepit and all fenced backyard
A bedroom with a bed, two bedside tables, a lamp, an air conditioning unit, a patterned rug, and a painting on the wall.

16. Renovated Beachside Retreat

Renovated Beachside Retreat
Milford
The price is £300
includes taxes & fees
5 Nov - 6 Nov
Renovated Beachside Retreat
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

17. 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, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is £263
includes taxes & fees
15 Oct - 16 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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.
5BR Beach Home | Walk to Cove Beach + Private Yard
A living room with a sofa set, a coffee table, and a television on a stand.

19. 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 £454
includes taxes & fees
16 Oct - 17 Oct
Spacious Stamford Home | Family, Work, Parking
A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

20. 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, (31 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 £754
includes taxes & fees
20 Oct - 21 Oct
5BR Beach House, Water Views, Steps to Beach, Backyard
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Weston Hotel Reviews

Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

8/10 Good
"We stayed for a friend’s wedding. The room was okay, except the USB port was not working so we were not able to charge our phones. The room was cozy with enough space and storage, but was very dark, it was a challenge to do a formal make up."
Pal 2-night trip
Posted less than an hour ago
Heritage Hotel, Golf & Conference Center

Find out more about Weston

Weston Holiday Homes information

Number of reviews
338
Accommodation
283 Holiday Homes
Lowest Price
£118
Highest Price
£977