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Westport Holiday Rentals

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Our top choices for Westport holiday rentals

Apartment in Westport

Spacious Studio with Pool Table
8.6 out of 10, Excellent, (7)
"So cute and comfortable "
United States
Maria
The price is NZ$478
includes taxes & fees
31 Dec - 1 Jan 2026
Spacious Studio with Pool Table

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.2 out of 10, (82)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
The price is NZ$218
includes taxes & fees
4 Jan - 5 Jan 2026
Stamford Suites

Aparthotel in West Norwalk

The Mansion Hotel-style
2.5 star property
8.2 out of 10, Very good, (22)
"Great service and very clean 👌 "
United States
JEAN
The price is NZ$163
includes taxes & fees
1 Jan - 2 Jan 2026
The Mansion Hotel-style

Aparthotel in Historic District

Guesthouse at Norwalk Inn
3.5 star property
8.6 out of 10, Excellent, (41)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is NZ$506
includes taxes & fees
3 Jan - 4 Jan 2026
Guesthouse at Norwalk Inn

Apartment in West End - West Side

Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is NZ$483
includes taxes & fees
7 Jan - 8 Jan 2026
Renovated 2BR Retreat / Modern Comforts Included
9.0 out of 10, Wonderful, (2)
"Very convenient location to everything in Bridgeport. Very easy and explicit check in directions! The unit was very clean!"
United States
Kelly
The price is NZ$658
includes taxes & fees
7 Jan - 8 Jan 2026
Enjoy the Venues of downtown Bridgeport's vibrant energy, at Park City Place.
10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is NZ$539
includes taxes & fees
9 Jan - 10 Jan 2026
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
10.0 out of 10, Exceptional, (2)
"Wonderful "
United States
Nolufefe Z.
The price is NZ$669
includes taxes & fees
9 Jan - 10 Jan 2026
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
2.0 star property
9.0 out of 10, Wonderful, (2)
"Had a great stay!"
United States
Garry G.
The price is NZ$710
includes taxes & fees
4 Jan - 5 Jan 2026
Beach Apartment in Woodmont Milford
9.4 out of 10, Exceptional, (12)
"This location is great close to highway and mall."
United States
Sansia D.
The price is NZ$838
includes taxes & fees
30 Dec - 31 Dec
Updated, cozy single family in Fairfield County
10.0 out of 10, Exceptional, (16)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is NZ$312
includes taxes & fees
7 Jan - 8 Jan 2026
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Apartment in Brooklawn - St. Vincent

Luxury Designer 2 bedroom+office/3bed vacation home.
9.4 out of 10, Exceptional, (22)
"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 NZ$825
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury Designer 2 bedroom+office/3bed vacation home.
10.0 out of 10, Exceptional, (23)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is NZ$824
includes taxes & fees
27 Jan - 28 Jan 2026
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
9.4 out of 10, Exceptional, (3)
"Very nice house....loved the front enclosed porch, and the kitchen was amazing with everything we needed. The deck with the Blackstone Grill was a great place to sit and relax. We enjoyed many of the nearby restaurants too. Matt and Jess were great hosts!J&J, Mooresville, NC"
United States
Jena
The price is NZ$632
includes taxes & fees
29 Dec - 30 Dec
The ARLO - Walk to Brewery and Restaurants
10.0 out of 10, Exceptional, (11)
"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 NZ$821
includes taxes & fees
27 Jan - 28 Jan 2026
Bright Escape, Top-Rated Design, Fire pit, Near Beach
10.0 out of 10, Exceptional, (3)
"Wonderful beach house. We loved staying here! The house is a historic gem and the accommodations were perfect. We enjoyed fabulous fireworks on the deck and walking the beach each morning. We can’t wait to go back. "
United States
Jane S.
The price is NZ$1,213
includes taxes & fees
9 Jan - 10 Jan 2026
Spacious 4-bedroom house with WiFi and AC in awesome Milford
9.8 out of 10, Exceptional, (8)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is NZ$771
includes taxes & fees
28 Dec - 29 Dec
Marine Theme - 4 BR - Backyard - Fire pit
9.6 out of 10, Exceptional, (23)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
The price is NZ$425
includes taxes & fees
1 Jan - 2 Jan 2026
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Holiday Home in Stratford

#37 - Luxury Collection
2.0 star property
8.0 out of 10, Very good, (4)
"We enjoyed the coziest getaway at this property. Newly renovated, clean and tucked away without being accessible to local attractions. "
United States
Sarah T.
The price is NZ$1,284
includes taxes & fees
31 Dec - 1 Jan 2026
#37 - Luxury Collection
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 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 NZ$218 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 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 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.