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Our top choices for Westport vacation homes

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 ¥25,148
¥47,483 total
includes taxes & fees
Apr 7 - Apr 8
Centric property close to all the great things in the city

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)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is ¥33,690
¥76,983 total
includes taxes & fees
Apr 13 - Apr 14
Captain's Cottage - Cold Spring Harbor Water Views

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (53 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is ¥13,572
¥23,392 total
includes taxes & fees
Apr 7 - Apr 8
Business or Weekend escape

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 ¥25,723
¥54,012 total
includes taxes & fees
Apr 14 - Apr 15
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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 ¥29,028
¥77,491 total
includes taxes & fees
Apr 8 - Apr 9
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

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 ¥45,698
¥108,437 total
includes taxes & fees
Apr 7 - Apr 8
The B&W Haven 5BR Home with yard theater + Office

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 ¥45,445
¥90,595 total
includes taxes & fees
Apr 8 - Apr 9
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

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, (29 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is ¥21,412
¥44,264 total
includes taxes & fees
Apr 20 - Apr 21
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (22 reviews)
"Great location for visiting Stamford, right on the water, a short walk from the beach, a short drive from the ShopRite. Liked the pool table. Excellent kitchen. Backyard seemed very nice but didn't use it due to weather. Easily parks 5 cars, and off-season (Oct-Apr) there is parking at the beach nearby."
United States
Eric K.
The price is ¥50,615
¥119,652 total
includes taxes & fees
Apr 7 - Apr 8
Waterview House Walking Distance from Cove Beach

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 ¥75,524
¥159,317 total
includes taxes & fees
Apr 7 - Apr 8
New Beach Home near Stamford Downtown/Shippan

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 ¥107,777
¥137,835 total
includes taxes & fees
Apr 30 - May 1
Beach house in Milford, CT

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 ¥34,808
¥87,371 total
includes taxes & fees
Apr 26 - Apr 27
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family-Friendly Retreat w/ Trampoline & Grill

Family-Friendly Retreat w/ Trampoline & Grill
Locust Valley
The price is ¥23,951
¥66,305 total
includes taxes & fees
Apr 7 - Apr 8
Family-Friendly Retreat w/ Trampoline & Grill

Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit
North End
9.6 out of 10, Exceptional, (9 reviews)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is ¥25,052
¥66,133 total
includes taxes & fees
Apr 7 - Apr 8
Marine Theme - 4 BR - Backyard - Fire pit

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 ¥29,315
¥78,101 total
includes taxes & fees
Apr 7 - Apr 8
Retreat with Heated Salt Water Pool, 1 Mile to NYC Train

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is ¥142,984
¥220,317 total
includes taxes & fees
Apr 7 - Apr 8
Beechmont - Perfect for Family Retreat!

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, (30 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 ¥32,253
¥79,763 total
includes taxes & fees
Apr 20 - Apr 21
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
The price is ¥38,225
¥89,305 total
includes taxes & fees
Apr 8 - Apr 9
Spacious Retreat with Game Room and Fire Pit

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
9.6 out of 10, Exceptional, (9 reviews)
"Beautiful old home with tons of space!"
United States
Rebeccca H.
The price is ¥140,110
¥253,337 total
includes taxes & fees
Apr 7 - Apr 8
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Stunning 5BR Oasis | 3-Acre Estate & Gorg View

Stunning 5BR Oasis | 3-Acre Estate & Gorg View
Oyster Bay
The price is ¥92,209
¥195,662 total
includes taxes & fees
Apr 7 - Apr 8
Stunning 5BR Oasis | 3-Acre Estate & Gorg View
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

Find out more about Westport

Westport Vacation Homes information

Number of reviews
311
Accommodation
337 Vacation Homes
Lowest Price
¥23,392
Highest Price
¥253,337