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Holiday Homes in Westport

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Our top choices for Westport holiday homes

Spacious Family Home

Spacious Family Home
Westport
10.0 out of 10, Exceptional, (1 review)
"We had a getaway weekend for a close friend group from college. This location could not have been better! We had everything we needed. Four bedrooms and three full bathrooms and across the street, a bakery, pizza place, fantastically stocked market, and a nice restaurant! A short drive allowed us to enjoy shopping and more food choices, as well as giving our Manhattan friend easy access to the train. Really could not have been a better place for us. Communication with the host was timely,...
United States
Laura B.
The price is AU$1,794
includes taxes & fees
7 July - 8 July
Spacious Family Home

Elite room stay

Elite room stay
Bridgeport
The price is AU$495
includes taxes & fees
27 June - 28 June
Elite room stay

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, (41 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AU$513
includes taxes & fees
30 June - 1 July
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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 AU$579
includes taxes & fees
28 June - 29 June
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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
7.2 out of 10, Good, (15 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is AU$387
includes taxes & fees
28 June - 29 June
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, (80 reviews)
"A true port in the storm"
United States
Trey S.
The price is AU$988
includes taxes & fees
7 July - 8 July
Captain's Cottage - Cold Spring Harbor Water Views

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is AU$489
includes taxes & fees
29 June - 30 June
Stamford Hideaway w/ Fire Pit

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 Daydreamer - Walk To Walnut Beach, Restaurant + Shops

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 AU$215
includes taxes & fees
27 June - 28 June
Business or Weekend escape

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, (37 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is AU$906
includes taxes & fees
28 June - 29 June
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is AU$562
includes taxes & fees
8 July - 9 July
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

171 Broadway · Renovated House Steps Away From The Ocean

171 Broadway · Renovated House Steps Away From The Ocean
Milford
8.4 out of 10, Very good, (8 reviews)
"very clean, new and great location! Will book again."
United States
ScottTakacs a.
The price is AU$646
includes taxes & fees
1 July - 2 July
171 Broadway · Renovated House Steps Away From The Ocean

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 AU$774
includes taxes & fees
30 June - 1 July
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

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

Luxury Loft •Pool • Gym • Free Parking • Near Yale
Orange
The price is AU$379
includes taxes & fees
28 June - 29 June
Luxury Loft •Pool • Gym • Free Parking • Near Yale

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)
The price is AU$928
includes taxes & fees
28 June - 29 June
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is AU$1,523
includes taxes & fees
27 June - 28 June
Beechmont - Perfect for Family Retreat!

4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
The price is AU$1,087
includes taxes & fees
7 July - 8 July
4 Mi to Beach & Dtwn! Charming Fairfield Home

Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!

Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
Milford
9.8 out of 10, Exceptional, (8 reviews)
"This area is fantastic, conveniently located near all the main attractions the town has to offer. We were thrilled to be so close to the beach! The host was incredibly friendly and went above and beyond to make us feel welcome. They even had a special welcome card that made us feel right at home from the moment we stepped inside. We’re definitely planning to book this property again in the future! "
United States
Clarissa G.
The price is AU$860
includes taxes & fees
8 July - 9 July
Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!

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

Modern + Spacious 5BR/2BA Home, Renovated Backyard
West End - West Side
9.6 out of 10, Exceptional, (5 reviews)
"Used for family weekend at SHU. Convenient location and plenty of space for the whole family! "
United States
Laurene S.
The price is AU$1,122
includes taxes & fees
29 June - 30 June
Modern + Spacious 5BR/2BA Home, Renovated Backyard

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (28 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
The price is AU$1,498
includes taxes & fees
22 July - 23 July
Waterview House Walking Distance from Cove Beach
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
Accommodation
313 Holiday Homes
Lowest Price
AU$1,523
Highest Price
AU$1,988