Clouds reflected in the Aspetuck Resevoir, Fairfield County, Connecticut.

Weston Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Weston vacation rentals

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 AED 514
AED 852 total
includes taxes & fees
23 Jun - 24 Jun
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (55 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 AED 312
AED 538 total
includes taxes & fees
23 Jun - 24 Jun
Business or Weekend escape
Private kitchen

Elite room stay

Elite room stay
Bridgeport
The price is AED 760
AED 1,264 total
includes taxes & fees
23 Jun - 24 Jun
Elite room stay
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 AED 579
AED 983 total
includes taxes & fees
23 Jun - 24 Jun
Centric property close to all the great things in the city
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
The price is AED 317
AED 801 total
includes taxes & fees
23 Jun - 24 Jun
Private Apartment in Southbury 104
Classic Suite | 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, (93 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is AED 657
AED 980 total
includes taxes & fees
24 Jun - 25 Jun
DUNE Fairfield Beach
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, (40 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AED 612
AED 1,159 total
includes taxes & fees
6 Jul - 7 Jul
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AED 823
AED 1,534 total
includes taxes & fees
25 Jun - 26 Jun
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Fridge, microwave, oven, stovetop

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 AED 566
AED 1,318 total
includes taxes & fees
25 Jun - 26 Jun
Modern 2 Bed in BlackRock
Smart TV

Luxury Loft •Pool • Gym • Free Parking • Near Yale

Luxury Loft •Pool • Gym • Free Parking • Near Yale
Orange
The price is AED 506
AED 937 total
includes taxes & fees
23 Jun - 24 Jun
Luxury Loft •Pool • Gym • Free Parking • Near Yale
TV, books

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is AED 696
AED 1,915 total
includes taxes & fees
23 Jun - 24 Jun
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
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, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AED 536
AED 845 total
includes taxes & fees
23 Jun - 24 Jun
The Perch in the Purchase -- Cozy, unique, and private
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 AED 496
AED 1,089 total
includes taxes & fees
24 Jun - 25 Jun
Zen, Spacious & Comfy 2 bed, Lux beds
Shower, towels, soap, toilet paper

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is AED 496
AED 999 total
includes taxes & fees
23 Jun - 24 Jun
Charming 1-bedroom apartment in Carmel with WiFi, AC
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is AED 542
AED 1,337 total
includes taxes & fees
29 Jun - 30 Jun
Stamford Hideaway w/ Fire Pit
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, (14 reviews)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is AED 1,455
AED 2,798 total
includes taxes & fees
30 Jun - 1 Jul
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Marina

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops
Milford
9.6 out of 10, Exceptional, (19 reviews)
"Cute very small house"
United States
Patricia M.
The price is AED 735
AED 1,662 total
includes taxes & fees
6 Jul - 7 Jul
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops
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 AED 529
AED 1,148 total
includes taxes & fees
27 Jun - 28 Jun
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Fridge, microwave, oven, stovetop

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 AED 536
AED 1,255 total
includes taxes & fees
25 Jun - 26 Jun
Renovated 2BR Retreat / Modern Comforts Included
Terrace/patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (2 reviews)
"Host was attentive and the space was comfortable and exactly what we needed"
United States
Parker M.
The price is AED 555
AED 1,285 total
includes taxes & fees
29 Jun - 30 Jun
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
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
"The Staff at the Hyatt in Old Greenwich is amazing!! They anticipated my every requirement and made sure I could get to every event on time. They made me feel at home."
Donna 2-night trip
Posted 6 hours ago
Hyatt Regency Greenwich

Explore a world of travel with Expedia

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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental outside of Weston offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 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.