A calm river reflecting buildings and trees, with a clear sky above.

Westport Holiday Rentals

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Our top choices for Westport holiday rentals

1. 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 NZ$478
includes taxes & fees
19 Aug - 20 Aug
Spacious Studio with Pool Table

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 NZ$702
includes taxes & fees
8 Sept - 9 Sept
Guesthouse at Norwalk Inn

3. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (104 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
The price is NZ$450
includes taxes & fees
13 Sept - 14 Sept
DUNE Fairfield Beach

4. 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)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
United States
Melissa H.
The price is NZ$1,304
includes taxes & fees
30 Aug - 31 Aug
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

5. 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 NZ$710
includes taxes & fees
23 Aug - 24 Aug
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

6. Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is NZ$1,460
includes taxes & fees
19 Aug - 20 Aug
Stareway to Heaven in Fairfield

7. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is NZ$391
includes taxes & fees
16 Aug - 17 Aug
2-bedroom apartmet No cleaning Fee

8. 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 NZ$1,543
includes taxes & fees
23 Aug - 24 Aug
5 minute walk to beach, walk to town & train

9. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NZ$2,013
includes taxes & fees
16 Aug - 17 Aug
Beechmont - Perfect for Family Retreat!

10. 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, (16 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 NZ$391
includes taxes & fees
15 Aug - 16 Aug
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

11. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (157 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is NZ$276
includes taxes & fees
23 Aug - 24 Aug
Stamford Suites

12. 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, (7 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 NZ$1,613
includes taxes & fees
25 Aug - 26 Aug
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

13. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, Exceptional, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
The price is NZ$1,337
includes taxes & fees
2 Sept - 3 Sept
Spacious Retreat with Game Room and Fire Pit

14. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is NZ$810
includes taxes & fees
14 Aug - 15 Aug
Cozy 1-bedroom house in welcoming Bridgeport

15. 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 NZ$1,176
includes taxes & fees
31 Aug - 1 Sept
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

16. 5BR Beach House, Water Views, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"We loved this house! The view is gorgeous and it's close to everything we needed. The pool table was a fun bonus!"
United States
Laura M.
The price is NZ$1,517
includes taxes & fees
18 Aug - 19 Aug
5BR Beach House, Water Views, Game Room, Backyard

17. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (8 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is NZ$1,304
includes taxes & fees
23 Aug - 24 Aug
Spacious Stamford Home | Family, Work, Parking

18. Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is NZ$698
includes taxes & fees
19 Aug - 20 Aug
Modern Luxe 1BR Apt in Downtown Stamford

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (26 reviews)
"The condo was redone and the beds were extremely comfortable.. Everything on the inside is brand new.. We were down from northeastern connecticut to stay for graduation.So we were really only there to sleep.."
United States
Mike P.
The price is NZ$819
includes taxes & fees
11 Sept - 12 Sept
Luxury Designer 2 bedroom+office/3bed vacation home.

20. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.4 out of 10, Exceptional, (20 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
The price is NZ$1,393
includes taxes & fees
8 Sept - 9 Sept
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Westport holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Westport. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Westport. Seeing all the best attractions is bound to make you fall in love with Westport. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Westport short-term rentals, that won’t be hard to do.

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?

Charming Home in Seaside: This holiday home rental outside of Westport is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Westport?

Expedia has 55 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.