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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Weston vacation rentals

A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (112 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is ￥28,427
￥42,463 total
includes taxes & fees
Sep 28 - Sep 29
DUNE Fairfield Beach
A bedroom with a bed, bedside tables, a mirror, and a patterned rug.

2. 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 ￥23,341
￥43,355 total
includes taxes & fees
Sep 28 - Sep 29
Spacious Studio with Pool Table
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

3. 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 ￥34,078
￥39,189 total
includes taxes & fees
Sep 14 - Sep 15
Guesthouse at Norwalk Inn
A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

4. 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, (17 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
The price is ￥22,229
￥36,360 total
includes taxes & fees
Sep 6 - Sep 7
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A modern kitchen with white cabinetry, a granite countertop, and a built-in island with bar stools.

5. 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 ￥21,435
￥46,919 total
includes taxes & fees
Sep 7 - Sep 8
Zen, Spacious & Comfy 2 bed, Lux beds
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

6. 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 ￥25,008
￥42,018 total
includes taxes & fees
Sep 4 - Sep 5
Centric property close to all the great things in the city
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (26 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveler
The price is ￥21,912
￥64,576 total
includes taxes & fees
Sep 14 - Sep 15
Luxury Designer 2 bedroom+office/3bed vacation home.
A living room with a sofa, a glass coffee table, a fireplace, and a television.

8. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is ￥37,155
￥67,498 total
includes taxes & fees
Oct 4 - Oct 5
Gilded Age Luxury Surrounded by Nature
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

9. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 reviews)
"Cozy get away"
United States
Anonymous traveler
The price is ￥21,407
￥52,682 total
includes taxes & fees
Sep 15 - Sep 16
Modern 2 Bed in BlackRock
A modern kitchen with a white refrigerator, a stove, and a sink. There are four wicker chairs around a white table.

10. 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 ￥20,451
￥50,511 total
includes taxes & fees
Sep 21 - Sep 22
Renovated 2BR Retreat / Modern Comforts Included
A swimming pool at night with blue lighting.

11. 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 ￥14,290
￥24,174 total
includes taxes & fees
Sep 29 - Sep 30
Business or Weekend escape
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

12. Elite room stay

Elite room stay
Bridgeport
The price is ￥32,867
￥54,151 total
includes taxes & fees
Sep 5 - Sep 6
Elite room stay
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

13. 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 ￥50,968
￥116,312 total
includes taxes & fees
Sep 30 - Oct 1
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

14. 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 ￥43,506
￥103,969 total
includes taxes & fees
Sep 21 - Sep 22
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

15. The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry

The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
Brooklawn - St. Vincent
The price is ￥26,842
￥62,783 total
includes taxes & fees
Sep 21 - Sep 22
The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
A modern living room with a large window, a sofa, a coffee table, and a TV.

16. 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
9.6 out of 10, Exceptional, (12 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is ￥17,307
￥30,541 total
includes taxes & fees
Sep 28 - Sep 29
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
A room with a large arched window, a bed, a bedside table, a lamp, and a potted plant.

17. 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 ￥22,229
￥36,360 total
includes taxes & fees
Sep 6 - Sep 7
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
A modern living room with a sofa, a coffee table, and a bar stool.

18. 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)
"loved walking the city. pizza was good."
United States
michelle b.
The price is ￥22,864
￥49,476 total
includes taxes & fees
Sep 5 - Sep 6
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

19. 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, (18 reviews)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is ￥42,394
￥103,326 total
includes taxes & fees
Sep 30 - Oct 1
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
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

The Circle Hotel Fairfield

The Circle Hotel Fairfield

8/10 Good
"Rooms were clean and tidy but a little dated Breakfast was ok for contimental Staff were great"
Stephen 2-night trip
Posted 2 hours ago
The Circle Hotel Fairfield

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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  • 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 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?

Charming Home in Seaside: This vacation home rental outside of Weston is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Weston?

Choose from 13 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 Norwalk Maritime Aquarium, 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.