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Holiday Rentals in Westport

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Holiday Rentals in Westport

Sweet Studio w/ Lounge & Pool Table

Westport
8.8 out of 10, Excellent, (6)
"So cute and comfortable "
United States
Maria
The price is €246
includes taxes & fees
1 Dec - 2 Dec
Sweet Studio w/ Lounge & Pool Table

Stamford Suites

4.0 star property
Downtown Stamford
6.2 out of 10, (76)
"It was great"
United States
Natalie
The price is €119
includes taxes & fees
8 Dec - 9 Dec
Stamford Suites

DUNE Fairfield Beach

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (76)
"Loved this venue! "
United States
adriano
DUNE Fairfield Beach

Luxury Apartments by Hyatus at The Asher

4.5 star property
Downtown Stamford
10.0 out of 10, Exceptional, (19)
"Clean and had everything you need for longer stay Comfortable "
United States
christine
Luxury Apartments by Hyatus at The Asher

Guesthouse at Norwalk Inn

3.5 star property
Norwalk
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 €289
includes taxes & fees
1 Dec - 2 Dec
Guesthouse at Norwalk Inn

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich
9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is €223
includes taxes & fees
1 Dec - 2 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is €126
includes taxes & fees
30 Nov - 1 Dec
Business or Weekend escape

Beechmont - Perfect for Family Retreat!

5.0 star property
North End
The price is €1,019
includes taxes & fees
1 Dec - 2 Dec
Beechmont - Perfect for Family Retreat!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

North End
9.6 out of 10, Exceptional, (4)
"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 €1,226
includes taxes & fees
30 Nov - 1 Dec
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Milford
10.0 out of 10, Exceptional, (133)
"Wonderful stay in a nice quiet neighborhood "
United States
Jacob M.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Northport
9.4 out of 10, Exceptional, (13)
"All went well. Owners live in cottage on property. The bay is gorgeous."
United States
Rob M.
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

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

Brooklawn - St. Vincent
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 €397
includes taxes & fees
28 Nov - 29 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.

Peaceful Vintage Home with Private Pond in Redding, CT.

2.0 star property
Redding
10.0 out of 10, Exceptional, (2)
"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 €672
includes taxes & fees
30 Nov - 1 Dec
Peaceful Vintage Home with Private Pond in Redding, CT.

Beach house in Milford, CT

Milford
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.
Beach house in Milford, CT

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

Downtown Bridgeport
10.0 out of 10, Exceptional, (2)
"Ricardo’s place was perfect for our needs! A small, clean and cozy place, not far from our daytime destination, the apartment offers all the basics - kitchenette, nice bathroom and modern shower, a comfy Queen Size bed, and even some snacks and essentials for a comfortable stay. The area has some restraunts and bars nearby too, though we were happy to stay in and watch some Netflix. I would highly recommend this apartment to a friend, and Ricardo has been a pleasure. Thanks so much!"
United States
Anonymous traveller
The price is €146
includes taxes & fees
30 Nov - 1 Dec
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Spacious 4-bedroom house in serene East Northport. 25 minutes from RYDER cup!

2.0 star property
East Northport
Spacious 4-bedroom house in serene East Northport. 25 minutes from RYDER cup!

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

2.0 star property
Kings Park
10.0 out of 10, Exceptional, (12)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
The price is €159
includes taxes & fees
4 Dec - 5 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Shelton
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is €175
includes taxes & fees
27 Nov - 28 Nov
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
The price is €431
includes taxes & fees
3 Dec - 4 Dec
Captain's Cottage - Cold Spring Harbor Water Views

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury
10.0 out of 10, Exceptional, (24)
"We enjoyed a fantastic vacation and the house had amazing views that were fabulous. Plenty of activities for children & adults and the boat rides capped off a perfect week! Sorry to see the week end. "
United States
Jack O.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
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, apart-hotels, 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 favorite 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 depends 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 €119 per night. Entering your travel dates in the search wizard you might find 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?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.: This holiday home rental outside of Westport is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Westport?

Expedia has 58 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 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 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.