Holiday Homes in Westport

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Our top choices for Westport holiday homes

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (75 reviews)
"Location was perfect!"
United States
Linda J P.
The price is €402
includes taxes & fees
20 Apr - 21 Apr
Captain's Cottage - Cold Spring Harbor Water Views

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
Stony Brook
7.4 out of 10, Good, (3 reviews)
"Very comfortable and welcoming Only problem was only one bathroom door closed the other one appeared to be in disrepair Other then that all was well"
United States
Kathleen
The price is €480
includes taxes & fees
26 Apr - 27 Apr
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

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 €228
includes taxes & fees
26 Apr - 27 Apr
Centric property close to all the great things in the city

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, (31 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is €248
includes taxes & fees
19 Apr - 20 Apr
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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, (11 reviews)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is €419
includes taxes & fees
20 Apr - 21 Apr
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is €308
includes taxes & fees
4 May - 5 May
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (54 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is €128
includes taxes & fees
19 Apr - 20 Apr
Business or Weekend escape

Modern + Spacious 5BR/2BA Home, Renovated Backyard

Modern + Spacious 5BR/2BA Home, Renovated Backyard
West End - West Side
9.6 out of 10, Exceptional, (4 reviews)
"Used for family weekend at SHU. Convenient location and plenty of space for the whole family! "
United States
Laurene S.
The price is €667
includes taxes & fees
19 Apr - 20 Apr
Modern + Spacious 5BR/2BA Home, Renovated Backyard

The B&W Haven 5BR Home with yard theater + Office

The B&W Haven 5BR Home with yard theater + Office
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (8 reviews)
"Lovely home with plenty of room! "
United States
David S.
The price is €573
includes taxes & fees
19 Apr - 20 Apr
The B&W Haven 5BR Home with yard theater + Office

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, (10 reviews)
"Clean and host was very helpful and accommodating. Highly recommend! "
United States
Brenna M.
The price is €496
includes taxes & fees
23 Apr - 24 Apr
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Beach house in Milford, CT

Beach house in Milford, CT
Milford
10.0 out of 10, Exceptional, (1 review)
"Beautiful Home right on the Long Island sound, we had such a great time. Beach was easily accessible, The Host’s were amazing and went above and beyond in accommodating us. Highly recommend!!!"
United States
Alex F.
The price is €671
includes taxes & fees
30 Apr - 1 May
Beach house in Milford, CT

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Kyra S.
The price is €886
includes taxes & fees
20 Apr - 21 Apr
New Beach Home near Stamford Downtown/Shippan

Newly renovated Private bedroom near Stony Brook University

Newly renovated Private bedroom near Stony Brook University
Stony Brook
8.0 out of 10, Very good, (2 reviews)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
The price is €275
includes taxes & fees
23 Apr - 24 Apr
Newly renovated Private bedroom near Stony Brook University

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, (31 reviews)
"Sweet and cozy home! The decor was lovely and everything was updated. Host was very responsive. We hope to come back again! "
United States
Jen R.
The price is €439
includes taxes & fees
23 Apr - 24 Apr
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Family-Friendly Retreat w/ Trampoline & Grill

Family-Friendly Retreat w/ Trampoline & Grill
Locust Valley
The price is €358
includes taxes & fees
19 Apr - 20 Apr
Family-Friendly Retreat w/ Trampoline & Grill

Historic Hideaway with Lake Access!

Historic Hideaway with Lake Access!
South Salem
9.8 out of 10, Exceptional, (22 reviews)
"Excellent stay! Very attentive hosts, nice location for a wedding that brought us to town"
United States
Molly S.
Historic Hideaway with Lake Access!

Salt & Blue - Walk to Beach - Near Tyde Wedding Venue

Salt & Blue - Walk to Beach - Near Tyde Wedding Venue
Milford
10.0 out of 10, Exceptional, (1 review)
"All was great and michael was a wonderful host! "
United States
Robin L.
Salt & Blue - Walk to Beach - Near Tyde Wedding Venue

Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit
North End
9.4 out of 10, Exceptional, (10 reviews)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is €341
includes taxes & fees
20 Apr - 21 Apr
Marine Theme - 4 BR - Backyard - Fire pit

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 €367
includes taxes & fees
21 Apr - 22 Apr
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Retreat with Heated Salt Water Pool, 1 Mile to NYC Train

Retreat with Heated Salt Water Pool, 1 Mile to NYC Train
Redding
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is €433
includes taxes & fees
20 Apr - 21 Apr
Retreat with Heated Salt Water Pool, 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 Westport Hotel Reviews

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Westport Holiday Homes information

Number of reviews
314
Accommodation
345 Holiday Homes
Lowest Price
€128
Highest Price
€886