Weston Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Weston holiday rentals

Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (24 reviews)
"Excellent host."
United States
David
The price is HK$714
HK$978 total
includes taxes & fees
31 Mar - 1 Apr
Cozy One Bedroom Apartment Centrally Located in Southbury
TV, offices

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
Milford
The price is HK$1,042
HK$2,463 total
includes taxes & fees
4 Apr - 5 Apr
Beach Apartment in Woodmont Milford 102
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (53 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is HK$666
HK$1,147 total
includes taxes & fees
31 Mar - 1 Apr
Business or Weekend escape
Smart TV

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
7.0 out of 10, Good, (14 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is HK$1,234
HK$2,337 total
includes taxes & fees
5 Apr - 6 Apr
Centric property close to all the great things in the city
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (3 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
The price is HK$684
HK$1,709 total
includes taxes & fees
31 Mar - 1 Apr
Private Apartment in Southbury 103
Property grounds

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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,234
HK$2,539 total
includes taxes & fees
31 Mar - 1 Apr
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

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, (28 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is HK$1,163
HK$2,262 total
includes taxes & fees
31 Mar - 1 Apr
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Outdoor pool

Cozy 1-bedroom apartment in lovely Oxford

Cozy 1-bedroom apartment in lovely Oxford
Oxford
10.0 out of 10, Exceptional, (3 reviews)
"This was my second time staying here. The apartment was immaculately clean and the owner was both professional and personal! The apartment had all the comforts of home, from coffee and snacks in the kitchen to self-care items (e.g., toothbrush, toothpaste, etc). Truly a hidden gem, close to shopping, restaurants, and highways! "
United States
LIsa G.
The price is HK$877
HK$1,256 total
includes taxes & fees
1 Apr - 2 Apr
Cozy 1-bedroom apartment in lovely Oxford
Interior

Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
The price is HK$754
HK$1,790 total
includes taxes & fees
31 Mar - 1 Apr
Private Apartment in Southbury 101
Interior

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
10.0 out of 10, Exceptional, (5 reviews)
"Nice little spot with a great host."
United States
J M.
The price is HK$901
HK$1,553 total
includes taxes & fees
1 Apr - 2 Apr
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Interior

Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.2 out of 10, Wonderful, (5 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
The price is HK$752
HK$1,787 total
includes taxes & fees
6 Apr - 7 Apr
Private Apartment in Southbury 102
Property grounds

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is HK$860
HK$1,209 total
includes taxes & fees
31 Mar - 1 Apr
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Fridge, microwave, stovetop, cookware/dishes/utensils

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
The price is HK$1,198
HK$2,498 total
includes taxes & fees
31 Mar - 1 Apr
Zen, Spacious & Comfy 2 bed, Lux beds
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
The price is HK$948
HK$2,028 total
includes taxes & fees
6 Apr - 7 Apr
Private Apartment in Southbury 104
Fridge, microwave, oven, stovetop

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, (11 reviews)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is HK$1,754
HK$4,250 total
includes taxes & fees
16 Apr - 17 Apr
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Outdoor dining

The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (1 review)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$1,057
HK$1,688 total
includes taxes & fees
31 Mar - 1 Apr
The Perch in the Purchase -- Cozy, unique, and private
Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (83 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is HK$1,303
HK$1,977 total
includes taxes & fees
12 Apr - 13 Apr
DUNE Fairfield Beach
Interior

Beach Apartment in Woodmont Milford

Beach Apartment in Woodmont Milford
Milford
8.8 out of 10, Excellent, (3 reviews)
"Had a great stay!"
United States
Garry G.
The price is HK$979
HK$2,704 total
includes taxes & fees
6 Apr - 7 Apr
Beach Apartment in Woodmont Milford
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is HK$1,128
HK$2,425 total
includes taxes & fees
2 Apr - 3 Apr
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Interior

Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22 reviews)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
The price is HK$1,159
HK$3,283 total
includes taxes & fees
1 Apr - 2 Apr
Luxury Designer 2 bedroom+office/3bed vacation home.
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 House Shelton

Hyatt House Shelton

8/10 Good
"Good"
Tyler 4-night trip
Posted 1 hour ago
Hyatt House Shelton

Find out more about Weston

Search for holiday rentals in Weston on Expedia! You can easily find your home rentals, villas, holiday apartments in Weston using one of the methods below:

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Look no further and take a look at our great range of rental properties in Weston!

Frequently asked questions

Can I find a holiday rental in Weston?

Yes, there are holiday rentals close to the most popular sights in Weston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Weston has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Weston offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Weston?

Choose from 13 Expedia holiday rentals in Weston for a memorable holiday.

What’s there to see and do in Weston?

While exploring the area, visit family-friendly sights like Stepping Stones Museum for Children, or get outside and enjoy nature at Lucius Pond Ordway / Devil's Den Preserve. Trout Brook Valley State Park Reserve and Wilton Historical Society are a couple of places you'll find in the wider area.

What’s a holiday rental in Weston like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Weston. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family getaway.