Westport Vacation Rentals

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Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Westport vacation rentals

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)
"There isn’t a “kitchen” but a minimum amenity was there and that was enough for me. Lots of dining options nearby. A quiet neighborhood and separate entry. Host was very responsive and accommodating. "
United States
Chihiro
The price is ￥22,611
￥42,403 total
includes taxes & fees
Apr 13 - Apr 14
Spacious Studio with Pool Table
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)
"This rental was great accommodation"
United States
Alma B.
The price is ￥25,079
￥47,034 total
includes taxes & fees
Mar 23 - Mar 24
Centric property close to all the great things in the city
Marina

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 ￥33,598
￥77,136 total
includes taxes & fees
Mar 30 - Mar 31
Captain's Cottage - Cold Spring Harbor Water Views
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, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is ￥23,646
￥46,620 total
includes taxes & fees
Mar 23 - Mar 24
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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 ￥24,362
￥51,105 total
includes taxes & fees
Mar 23 - Mar 24
Zen, Spacious & Comfy 2 bed, Lux beds
Fridge, microwave, oven, stovetop

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 ￥56,578
￥122,627 total
includes taxes & fees
Mar 25 - Mar 26
Modern + Spacious 5BR/2BA Home, Renovated Backyard
5 bedrooms, desk, iron/ironing board, travel crib

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 ￥45,572
￥107,501 total
includes taxes & fees
Mar 26 - Mar 27
The B&W Haven 5BR Home with yard theater + Office
Smart TV

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is ￥39,808
￥76,229 total
includes taxes & fees
Mar 23 - Mar 24
THE OASIS @ LONG ISLAND
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
10.0 out of 10, Exceptional, (5 reviews)
"Nice little spot with a great host."
United States
J M.
The price is ￥18,152
￥31,384 total
includes taxes & fees
Mar 25 - Mar 26
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Pool

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 ￥13,535
￥23,328 total
includes taxes & fees
Mar 26 - Mar 27
Business or Weekend escape
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (30 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is ￥35,031
￥61,376 total
includes taxes & fees
Mar 23 - Mar 24
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Fridge, microwave, oven, stovetop

Renovated Cape Near beach, with Fire Pit and BBQ

Renovated Cape Near beach, with Fire Pit and BBQ
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 ￥30,572
￥80,698 total
includes taxes & fees
Mar 23 - Mar 24
Renovated Cape Near beach, with Fire Pit and BBQ
1 bedroom, WiFi

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is ￥31,050
￥60,581 total
includes taxes & fees
Mar 23 - Mar 24
Luxe Provincial Style Studio w/ Patio & Parking
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is ￥22,929
￥49,775 total
includes taxes & fees
Mar 23 - Mar 24
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥27,865
￥55,770 total
includes taxes & fees
Apr 12 - Apr 13
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Interior

Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (22 reviews)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
The price is ￥26,798
￥70,945 total
includes taxes & fees
Mar 23 - Mar 24
Luxury Designer 2 bedroom+office/3bed vacation home.
Property grounds

Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is ￥26,655
￥65,127 total
includes taxes & fees
Mar 23 - Mar 24
Seabreeze at the beach west beach Stamford ct.
TV, offices

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
Milford
The price is ￥14,490
￥43,414 total
includes taxes & fees
Mar 25 - Mar 26
Beach Apartment in Woodmont Milford 102
Front of property

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is ￥142,590
￥219,709 total
includes taxes & fees
Mar 23 - Mar 24
Beechmont - Perfect for Family Retreat!
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, (83 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield 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

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"Beautiful room, nice (adjustable) temp, sparking clean shower. All staff were friendly and helpful. Nice quiet& restful night on our travels. Worth the price!"
Kim 1-night trip
Posted 3 hours ago
Norwalk Inn & Conference Center

Find out more about Westport

Search for holiday rentals in Westport on Expedia! You can easily find your home rentals, villas, holiday apartments in Westport using one of the methods below:

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Look no further and take a look at our great range of rental properties in Westport!

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 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.: This Westport vacation home rental offers a fireplace, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals will I find in Westport?

Expedia has 58 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 Old Mill Beach and Compo 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.