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Westport Holiday Rentals

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Our top choices for Westport holiday rentals

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is AU$435
includes taxes & fees
24 Aug - 25 Aug
Spacious Studio with Pool Table

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 AU$574
includes taxes & fees
23 Aug - 24 Aug
Guesthouse at Norwalk Inn

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (102 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
The price is AU$403
includes taxes & fees
25 Aug - 26 Aug
DUNE Fairfield Beach

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
"This house was so lovely, clean, cozy, and well-appointed - everything we could have asked for for a girls' weekend! And so close to the town of Westport with its excellent restaurants and shops. The best!"
United States
Rebecca H.
The price is AU$1,079
includes taxes & fees
4 Aug - 5 Aug
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
The price is AU$593
includes taxes & fees
23 Aug - 24 Aug
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

5 minute walk to beach, walk to town & train

5 minute walk to beach, walk to town & train
Fairfield Beach
10.0 out of 10, Exceptional, (26 reviews)
"Host was great. Had a great stay. "
United States
jeff d.
The price is AU$1,383
includes taxes & fees
1 Aug - 2 Aug
5 minute walk to beach, walk to town & train

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is AU$1,508
includes taxes & fees
29 July - 30 July
Beechmont - Perfect for Family Retreat!

Stareway to Heaven Su

Stareway to Heaven Su
Fairfield Beach
10.0 out of 10, Exceptional, (22 reviews)
"We really enjoyed our stay. Amazing house, super clean. We will definitely be back."
United States
Birgit S.
The price is AU$1,471
includes taxes & fees
26 Aug - 27 Aug
Stareway to Heaven Su

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 AU$934
includes taxes & fees
2 Aug - 3 Aug
4 Mi to Beach & Dtwn! Charming Fairfield Home

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is AU$331
includes taxes & fees
28 July - 29 July
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, Exceptional, (1 review)
"This property was outstanding! It was exceptionally clean and had everything we needed. The host made every step easy. 8 Adults stayed very comfortably with multiple gathering places for reconnecting. We had a small event with other family members and it was spacious and inviting. The kids had a great time in the game room. This is an excellent location for New Canaan, Darien and Norwalk. We will stay again if we are in the area."
United States
Carol R.
The price is AU$1,132
includes taxes & fees
4 Aug - 5 Aug
Spacious Retreat with Game Room and Fire Pit

2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is AU$334
includes taxes & fees
28 July - 29 July
2-bedroom apartmet No cleaning Fee

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (143 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is AU$235
includes taxes & fees
29 July - 30 July
Stamford Suites

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is AU$1,072
includes taxes & fees
18 Aug - 19 Aug
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (38 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is AU$969
includes taxes & fees
28 July - 29 July
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (16 reviews)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is AU$1,139
includes taxes & fees
26 Aug - 27 Aug
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is AU$1,796
includes taxes & fees
26 Aug - 27 Aug
Stareway to Heaven in Fairfield

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

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
8.8 out of 10, Excellent, (10 reviews)
"Plenty of bedrooms and space for the family. Very prompt communication with host."
United States
David K.
The price is AU$1,943
includes taxes & fees
28 July - 29 July
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

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, (42 reviews)
"rooms were lovely and spacious and hosts were responsive and helpful. "
United States
nina a.
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
United States
Erin D.
The price is AU$1,232
includes taxes & fees
29 July - 30 July
Stylish Beach Home near Stamford Downtown/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

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$213 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. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Westport?

Yes, there are holiday rentals in Westport close to Westport Arts Center, 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?

Spacious Family Home: This highly rated holiday home rental in Westport has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Another good choice for your trip to Westport is Westport Gem - walk to shops, dining, town center, pet-friendly.

How many holiday rentals will I find in Westport?

Expedia has 54 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.