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

Weston Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Weston holiday rentals

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, (98 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is HK$1,430
HK$2,123 total
includes taxes & fees
4 Aug - 5 Aug
DUNE Fairfield Beach
Front of property

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is HK$4,787
HK$8,249 total
includes taxes & fees
12 Jul - 13 Jul
Beechmont - Perfect for Family Retreat!
1 bedroom, desk, iron/ironing board, free WiFi

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is HK$855
HK$1,508 total
includes taxes & fees
12 Jul - 13 Jul
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Private kitchen

Elite room stay

Elite room stay
Bridgeport
The price is HK$1,623
HK$2,705 total
includes taxes & fees
12 Jul - 13 Jul
Elite room stay
Interior

4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is HK$3,481
HK$5,326 total
includes taxes & fees
2 Aug - 3 Aug
4 Mi to Beach & Dtwn! Charming Fairfield Home
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, (41 reviews)
"Room was great for the price and the host was a pleasure to deal with. "
United States
steven l.
The price is HK$1,482
HK$2,715 total
includes taxes & fees
14 Jul - 15 Jul
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Internet, bed sheets

Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
The price is HK$784
HK$1,444 total
includes taxes & fees
10 Jul - 11 Jul
Welcome to Sweet Abby Rose!
Property entrance

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is HK$2,814
HK$3,237 total
includes taxes & fees
12 Jul - 13 Jul
Guesthouse at Norwalk Inn
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
9.8 out of 10, Exceptional, (16 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,952
HK$3,523 total
includes taxes & fees
30 Jul - 31 Jul
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Smart TV

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is HK$2,462
HK$5,650 total
includes taxes & fees
22 Jul - 23 Jul
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
2 bedrooms, iron/ironing board, free WiFi, bed sheets

2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is HK$1,411
HK$1,819 total
includes taxes & fees
11 Jul - 12 Jul
2-bedroom apartmet No cleaning Fee
Beach nearby, sun-loungers, beach towels

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, (37 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is HK$2,596
HK$5,332 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Interior

4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
The price is HK$2,916
HK$5,320 total
includes taxes & fees
5 Aug - 6 Aug
4 Mi to Beach & Dtwn! Charming Fairfield Home
Microwave, oven, stovetop

Serene 2-bedroom spacious apartment

Serene 2-bedroom spacious apartment
Carmel Hamlet
The price is HK$1,372
HK$2,634 total
includes taxes & fees
16 Jul - 17 Jul
Serene 2-bedroom spacious apartment
Interior

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is HK$1,991
HK$3,669 total
includes taxes & fees
10 Jul - 11 Jul
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Fridge, microwave, oven, stovetop

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
The price is HK$3,191
HK$6,801 total
includes taxes & fees
13 Jul - 14 Jul
Stylish Beach Home near Stamford Downtown/Beach
TV

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Cove - East Side - Shippan
8.4 out of 10, Very good, (7 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is HK$1,461
HK$3,507 total
includes taxes & fees
10 Jul - 11 Jul
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
TV

Downtown 2br/1ba apartment -- free parking, outdoor patio & walk everywhere

Downtown 2br/1ba apartment -- free parking, outdoor patio & walk everywhere
Milford
10.0 out of 10, Exceptional, (1 review)
"Great location to town center."
United States
Anonymous traveller
The price is HK$3,528
HK$5,419 total
includes taxes & fees
10 Jul - 11 Jul
Downtown 2br/1ba apartment -- free parking, outdoor patio & walk everywhere
Fridge, microwave, oven, stovetop

Renovated 2 bedroom entire apartment w/parking

Renovated 2 bedroom entire apartment w/parking
Ansonia
10.0 out of 10, Exceptional, (2 reviews)
"Host was very attentive making sure everything was going well, apartment was great would definitely stay again "
United States
Sophia
The price is HK$1,190
HK$2,115 total
includes taxes & fees
12 Jul - 13 Jul
Renovated 2 bedroom entire apartment w/parking
TV, fireplace, table football, offices

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (25 reviews)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
The price is HK$4,476
HK$8,873 total
includes taxes & fees
13 Jul - 14 Jul
New Beach Home near Stamford Downtown/Shippan
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

10/10 Excellent
"Beautiful hotel with a good restaurant"
robert 1-night trip
Posted 2 hours ago
Hyatt Regency Greenwich

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:

  • View our selection of featured holiday rentals in Weston
  • Use the map to find apartments and other holiday homes in the Weston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Weston while they last

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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Weston is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Weston?

Choose from 12 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.