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Westport Holiday Rentals

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Holiday Rentals in Westport

Sweet Studio w/ Lounge & Pool Table
8.8 out of 10, Excellent, (6)
"So cute and comfortable "
United States
Maria
The price is AU$397
includes taxes & fees
28 Oct - 29 Oct
Sweet Studio w/ Lounge & Pool Table
Stamford Suites
4.0 star property
5.8 out of 10, (66)
"Location very good."
United States
Sheila
The price is AU$233
includes taxes & fees
27 Oct - 28 Oct
Stamford Suites
DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (74)
"Loved this venue! "
United States
adriano
DUNE Fairfield Beach
Luxury Apartments by Hyatus at The Asher
4.5 star property
10.0 out of 10, Exceptional, (18)
"This place truly felt like a home away from home. Everything was spotless, comfortable, and well cared for. The location made it easy to access everything we needed, whether dining, shopping, or exploring the area. I would definitely return!"
United States
Tasha
Luxury Apartments by Hyatus at The Asher
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (18)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is AU$296
includes taxes & fees
2 Nov - 3 Nov
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Guesthouse at Norwalk Inn
3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is AU$443
includes taxes & fees
18 Nov - 19 Nov
Guesthouse at Norwalk Inn
Business or Weekend escape
9.2 out of 10, Wonderful, (50)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$219
includes taxes & fees
27 Oct - 28 Oct
Business or Weekend escape
Beechmont - Perfect for Family Retreat!
5.0 star property
The price is AU$1,696
includes taxes & fees
29 Oct - 30 Oct
Beechmont - Perfect for Family Retreat!
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!
10.0 out of 10, Exceptional, (3)
"Very clean house. set up very nicely, landlord was very responsive and helpful. perfect for what we needed "
United States
Nancy H.
The price is AU$2,107
includes taxes & fees
27 Oct - 28 Oct
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!
Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (22)
"Beautifully appointed luxury 2 nd floor accommodations in the city of Bridgeport. Guests could comfortably stay for multiple nights with the well equipped kitchen and dining room space. "
United States
Tessa P.
The price is AU$754
includes taxes & fees
1 Nov - 2 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
9.2 out of 10, Wonderful, (12)
"This is a quiet and beautiful spot on the water. The outside space is perfect to relax or get some sun. The inside space was relaxing and very comfortable. The host, Richard was wonderful and very responsive. "
United States
Lori G.
The price is AU$1,059
includes taxes & fees
27 Oct - 28 Oct
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (70)
"Location was perfect!"
United States
Linda J P.
The price is AU$743
includes taxes & fees
10 Nov - 11 Nov
Captain's Cottage - Cold Spring Harbor Water Views
Centric property close to all the great things in the city
7.2 out of 10, Good, (13)
"This rental was great accommodation"
United States
Alma B.
The price is AU$465
includes taxes & fees
27 Oct - 28 Oct
Centric property close to all the great things in the city
Beach house in Milford, CT
10.0 out of 10, Exceptional, (1)
"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 AU$1,017
includes taxes & fees
28 Oct - 29 Oct
Beach house in Milford, CT
Newly renovated Private bedroom near Stony Brook University
2.0 star property
6.0 out of 10, (1)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
The price is AU$359
includes taxes & fees
27 Oct - 28 Oct
Newly renovated Private bedroom near Stony Brook University
Beautiful historic home in Stony Brook!
2.0 star property
8.6 out of 10, Excellent, (19)
"House is well located and very comfortable.We enjoyed our stay at the home."
United States
Jim D.
Beautiful historic home in Stony Brook!
Peaceful Vintage Home with Private Lake in Redding, CT.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
The price is AU$1,179
includes taxes & fees
3 Nov - 4 Nov
Peaceful Vintage Home with Private Lake in Redding, CT.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
10.0 out of 10, Exceptional, (130)
"Fantastic all around!"
United States
Risa S.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2.0 star property
10.0 out of 10, Exceptional, (11)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
The price is AU$278
includes taxes & fees
27 Oct - 28 Oct
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Modern 2 Bed in BlackRock
2.0 star property
6.8 out of 10, (3)
"Cozy get away"
United States
Anonymous traveller
The price is AU$570
includes taxes & fees
27 Oct - 28 Oct
Modern 2 Bed in BlackRock
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

Everything you need to know about Westport holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westport holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Westport holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Westport holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westport. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westport holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westport holiday rentals we have selected for you start as low as AU$219 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Westport rentals

At Expedia, we put the best Westport holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Westport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Westport holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Westport?

Yes, there are holiday rentals in Westport close to Earthplace Museum, or you can select a more secluded option if you're looking for a relaxing stay. Westport is known for its football games and waterfront. Make sure you have time to check out the entertainment choices and theatres during your trip.

What are some of the best holiday rentals that Westport has to offer?

Beechmont - Perfect for Family Retreat!: This holiday home rental outside of Westport is located near the airport, and has a private balcony, a terrace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. You can relax into your holiday with a private garden and a selection of games.

How many holiday rentals will I find in Westport?

Expedia has 57 holiday 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 holiday rental in Westport like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Westport. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for small groups.