We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Weston Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
48 rentals in Weston.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.

The Weston River House 1 hr from NYC Designed by Famed Artisan Michael Greenberg

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Interior Designer's Enchanting And Bucolic Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

A ZEN getaway in a Gorgeous WESTON setting

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Enchanting, cozy & secluded riverfront English cottage SANCTUARY

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Riverfront retreat in the woods of scenic Weston, Connecticut.

Rental Home
6 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Enjoy our Extraordinary Carriage House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Luxe CT Country Home w/ Hi-end WiFi for WFH & School

Rental Home
6 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Westport: Walk to Town (Really) Private Yard, One Floor, Fall 2020 Reno KHS BMS

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Romantic Riverfront Farm House at Historic Aspetuck Corners

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Entire Guest House at Fox Pond Farm with Access to In ground Pool

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Weston rentals sent straight to your email!

Charming Cottage located on Historic Estate 1 Hour from NYC!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

A private summer compound in Westport, CT - total seclusion yet close to it all

Rental Home
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The West Lane Inn - Double Queen Room

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

A New England Jewel with Scenic Beauty

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection

Modern Farmhouse - Recently Renovated

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Real log house on Directly on the River with heated pool one hour from NYC.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Lakefront getaway walkable to restaurants and shops

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Mid Century Modern Hilltop Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Summer in Westport, CT! - Renovated, Private, Close to everything!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Dramatic Waterfront Family Home Directly on the Saugatuck River in Westport, CT

Rental Home
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Family friendly home with an open floor plan on an acre of wooded land

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Updated Farmhouse Retreat

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Spectacular Country Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Westport on the Water: Pool, Dock & Boats--Casual Elegance--Walk to Town & Train

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Temporary out of service

Rental Home
0 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beautiful Summer Escape

Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Newly renovated summer home in Westport CT private pool & spa, near beach & town

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Suburban Getaway. Heated Pool. NO PARTIES.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Check in
Check out
Payment Protection

Available ONLY 6/23-7/4 for entire term

Rental Home
6 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport.

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Gorgeous French Normandy Estate-Privacy- Pool- with Contemporary Details Inside

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Cozy Apartment in Downtown Westport

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Nature Lovers Perfect Location, an hour from Manhattan

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

A Fine Waterfront Private Home, In Park-like seaing

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

See Beautiful Fall Foliage - Lovely CT country home sleeps 10 + heated pool!

Rental Home
6 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Westport Family Home 3 miles To Beach

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Vacation Ready: Beautiful House with Heated Pool

Rental Home
6 bedrooms
7 bathrooms
Sleeps 11
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Award Winning Private Pool House on Spectacular Historic and Rare 24-Acre Estate

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Walk-To-Town Gem! Charming renovated Colonial in sought after neighborhood.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The West Lane Inn - King Room

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

PRIVATE AIRY SUMMER HOME in Minutes from the BEACH and more (WESTPORT)

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The West Lane Inn - Deluxe Fireplace Double Queen

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The West Lane Inn - Deluxe Fireplace King

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Southern Connecticut House for a Summer Retreat with Pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The West Lane Inn - Family Suite

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

One Hour From New York City, Great Escape for nature lovers

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The West Lane Inn - Family Suite with Kitchenette

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Exquisite Westport Manor for Winter Vacation

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The West Lane Inn - Queen Room

Rental Home
1 bedroom
1 bathroom
Sleeps 1
More info
Vrbo.com logo
Check in
Check out

Pied-à-terre in prestigious Long Lots area of Westport

Rental Home
1 bedroom
1 bathroom
Sleeps 1
More info
Vrbo.com logo
Check in
Check out
PreviousNext
1
Frequently Asked Questions about Weston