A calm river reflecting buildings and trees, with a clear sky above.

Westport 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 Westport vacation rentals

Private kitchen

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 AED 2,663
AED 4,523 total
includes taxes & fees
7 Jul - 8 Jul
Spacious Family Home
1 bedroom, desk, WiFi, bed sheets

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is AED 713
AED 1,223 total
includes taxes & fees
12 Jul - 13 Jul
Spacious Studio with Pool Table
Smart TV, fireplace, books, stereo

Your Summer Retreat, Modern and Spacious 5-bed house in marvelous Westport, CT!

Your Summer Retreat, Modern and Spacious 5-bed house in marvelous Westport, CT!
Westport
10.0 out of 10, Exceptional, (7 reviews)
"Lovely, modern home close to Westport's main shopping street. Great for families and a very responsive host that made sure our stay was comfortable."
United States
Lauren I.
Your Summer Retreat, Modern and Spacious 5-bed house in marvelous Westport, CT!
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 845 total
includes taxes & fees
26 Jun - 27 Jun
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Private kitchen

Elite room stay

Elite room stay
Bridgeport
The price is AED 760
AED 1,253 total
includes taxes & fees
26 Jun - 27 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 976 total
includes taxes & fees
28 Jun - 29 Jun
Centric property close to all the great things in the city
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
2 Jul - 3 Jul
Business or Weekend escape
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, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is AED 745
AED 1,081 total
includes taxes & fees
29 Jun - 30 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, (41 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 790
AED 1,482 total
includes taxes & fees
28 Jun - 29 Jun
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is AED 440
AED 1,204 total
includes taxes & fees
29 Jun - 30 Jun
Stamford Hideaway w/ Fire Pit
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 1,093 total
includes taxes & fees
30 Jun - 1 Jul
Zen, Spacious & Comfy 2 bed, Lux beds
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 895
AED 2,175 total
includes taxes & fees
13 Jul - 14 Jul
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
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 619
AED 1,379 total
includes taxes & fees
28 Jun - 29 Jun
Modern 2 Bed in BlackRock
Smart TV

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is AED 1,154
AED 2,647 total
includes taxes & fees
3 Jul - 4 Jul
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
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 965 total
includes taxes & fees
28 Jun - 29 Jun
Luxury Loft •Pool • Gym • Free Parking • Near Yale
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 1,344
AED 2,634 total
includes taxes & fees
28 Jun - 29 Jun
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 Daydreamer - Walk To Walnut Beach, Restaurant + Shops
TV, fireplace, offices

Renovated 3BR Apt / Easy Check-In / FamilyFriendly

Renovated 3BR Apt / Easy Check-In / FamilyFriendly
West End - West Side
The price is AED 698
AED 1,567 total
includes taxes & fees
7 Jul - 8 Jul
Renovated 3BR Apt / Easy Check-In / FamilyFriendly
Interior

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
9.4 out of 10, Exceptional, (8 reviews)
"Nice little spot with a great host."
United States
J M.
The price is AED 393
AED 698 total
includes taxes & fees
6 Jul - 7 Jul
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
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

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"Great staff that really cared about guests. Pride in their jobs. Good managers!"
Kathy 2-night trip
Posted 6 hours ago
Norwalk Inn & Conference Center

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Frequently asked questions

Can I find vacation rentals in Westport?

Yes, there are vacation rentals in Westport near Westport Arts Center, or you can choose a more secluded option if you want a relaxing stay. Westport is known for its football games and waterfront. Make sure you have time to check out the entertainment choices and theaters during your trip.

What are some of the best vacation rentals in Westport?

Spacious Family Home: This Westport vacation home rental has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals will I find in Westport?

Expedia has 53 vacation rentals for your stay in Westport.

What’s there to see and do in Westport?

Family-friendly attractions include Earthplace Museum and Rolnick Observatory, whereas Compo Beach and Burying Hill Beach are a couple of great spots to enjoy the outdoors. Levitt Pavilion and Westport Country Playhouse are other places to visit while you're in town.

What’s a vacation rental in Westport like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Westport. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.