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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Westport vacation rentals

A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is ￥27,924
￥41,713 total
includes taxes & fees
Oct 7 - Oct 8
DUNE Fairfield Beach
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is ￥44,083
￥50,696 total
includes taxes & fees
Nov 1 - Nov 2
Guesthouse at Norwalk Inn
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

3. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is ￥95,838
￥145,636 total
includes taxes & fees
Oct 4 - Oct 5
4 Mi to Beach & Dtwn! Charming Fairfield Home
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

4. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (186 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is ￥22,985
￥26,433 total
includes taxes & fees
Oct 12 - Oct 13
Stamford Suites
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

5. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is ￥151,530
￥229,339 total
includes taxes & fees
Oct 11 - Oct 12
Beechmont - Perfect for Family Retreat!
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

6. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is ￥51,775
￥79,466 total
includes taxes & fees
Oct 16 - Oct 17
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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

The Circle Hotel Fairfield

The Circle Hotel Fairfield

10/10 Excellent
"The room was clean and very comfortable. The staff was very welcoming and considerate!"
April 1-night trip
Posted 2 hours ago
The Circle Hotel Fairfield

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:

  • View our selection of featured holiday rentals in Westport
  • Use the map to find apartments and other holiday homes in the Westport neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Westport while they last

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?

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends: This vacation home rental near Westport is located on the beach and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Westport?

Expedia has 54 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 Old Mill 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.