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

Weston Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Weston vacation rentals

Classic Suite | Iron/ironing board, WiFi (free), bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (100 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
The price is ￥29,047
￥43,310 total
includes taxes & fees
Aug 19 - Aug 20
DUNE Fairfield Beach
1 bedroom, desk, WiFi, bed sheets

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is ￥26,634
￥47,681 total
includes taxes & fees
Aug 17 - Aug 18
Spacious Studio with Pool Table
1 bedroom, desk, iron/ironing board, WiFi (free)

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 ￥22,736
￥37,514 total
includes taxes & fees
Jul 22 - Jul 23
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Standard Room, 1 King Bed, Main Building | 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 ￥55,678
￥64,030 total
includes taxes & fees
Jul 27 - Jul 28
Guesthouse at Norwalk Inn
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is ￥36,540
￥46,568 total
includes taxes & fees
Jul 28 - Jul 29
2-bedroom apartmet No cleaning Fee
Fridge, microwave, stovetop, cookware/dishes/utensils

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place. Beds where comfortable. Would most definitely come back there again. Quiet and safe atmosphere. Not far from the highway. Host was very nice."
United States
Lisa J.
The price is ￥21,924
￥48,152 total
includes taxes & fees
Jul 21 - Jul 22
Zen, Spacious & Comfy 2 bed, Lux beds
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
7.2 out of 10, Good, (15 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is ￥25,578
￥43,463 total
includes taxes & fees
Jul 22 - Jul 23
Centric property close to all the great things in the city
Private kitchen

Elite room stay

Elite room stay
Bridgeport
The price is ￥33,617
￥56,036 total
includes taxes & fees
Jul 21 - Jul 22
Elite room stay
Coffee/tea maker, fridge, microwave, oven

Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (4 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
The price is ￥24,867
￥58,276 total
includes taxes & fees
Jul 21 - Jul 22
Modern 2 Bed in BlackRock
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (58 reviews)
"I love the layout of this apt. Perfect for 2 to 3 people, it was clean and nothing out of place. The host was great and communicated well. I will be looking for this place again next year."
United States
Shamel
The price is ￥13,804
￥23,792 total
includes taxes & fees
Jul 27 - Jul 28
Business or Weekend escape
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 ￥51,010
￥117,045 total
includes taxes & fees
Jul 22 - Jul 23
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Smart TV, fireplace, books, stereo

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, (13 reviews)
"This house was so lovely, clean, cozy, and well-appointed - everything we could have asked for for a girls' weekend! And so close to the town of Westport with its excellent restaurants and shops. The best!"
United States
Rebecca H.
The price is ￥51,010
￥114,642 total
includes taxes & fees
Jul 23 - Jul 24
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
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
9.4 out of 10, Exceptional, (9 reviews)
"Nice little spot with a great host."
United States
J M.
The price is ￥18,026
￥31,611 total
includes taxes & fees
Jul 28 - Jul 29
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
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)
"rooms were lovely and spacious and hosts were responsive and helpful. "
United States
nina a.
The price is ￥30,694
￥56,248 total
includes taxes & fees
Jul 26 - Jul 27
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 ￥16,240
￥29,921 total
includes taxes & fees
Jul 22 - Jul 23
Welcome to Sweet Abby Rose!
Dining

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
The price is ￥56,678
￥72,488 total
includes taxes & fees
Jul 26 - Jul 27
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (139 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is ￥24,198
￥27,828 total
includes taxes & fees
Aug 2 - Aug 3
Stamford Suites
Coffee/tea maker, fridge, microwave, oven

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveler
The price is ￥34,026
￥68,849 total
includes taxes & fees
Aug 11 - Aug 12
Renovated 2BR Retreat / Modern Comforts Included
1 bedroom, desk, iron/ironing board, WiFi (free)

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (8 reviews)
"The Orange & Groovy Apt. was as described. All the amenities we needed and we had a lovely time and enjoyed the area. Will book again!"
United States
Betty W.
The price is ￥22,736
￥37,352 total
includes taxes & fees
Jul 26 - Jul 27
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
House (4 Bedrooms) | 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 ￥68,208
￥105,856 total
includes taxes & fees
Aug 2 - Aug 3
4 Mi to Beach & Dtwn! Charming Fairfield 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 Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"love this hyatt!!! great hitel. great staff. clean. great location"
Richard 2-night trip
Posted less than an hour 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
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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 vacation rental in Weston?

Yes, there are vacation rentals close to well known attractions in Weston, or you can choose a secluded option if you want a relaxing place to stay.

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

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation 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 vacation rentals are there in Weston?

Choose from 12 Expedia vacation rentals in Weston for a memorable vacation.

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 larger area.

What’s a vacation rental in Weston like?

Vacation rentals are private properties you can reserve for a short or long stay in Weston. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.