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

Westport Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Westport vacation rentals

1 bedroom, desk, WiFi, bed sheets

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 AED 577
AED 1,060 total
includes taxes & fees
8 Sep - 9 Sep
Spacious Studio with Pool Table
Standard Room, 1 King Bed, Main Building | Property entrance

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 AED 1,259
AED 1,448 total
includes taxes & fees
16 Aug - 17 Aug
Guesthouse at Norwalk Inn
Classic Suite | Iron/ironing board, WiFi (free), bed sheets

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 AED 647
AED 969 total
includes taxes & fees
13 Sep - 14 Sep
DUNE Fairfield Beach
Smart TV, fireplace, books, stereo

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 AED 1,241
AED 2,830 total
includes taxes & fees
7 Sep - 8 Sep
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Dining

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 AED 1,208
AED 1,555 total
includes taxes & fees
23 Aug - 24 Aug
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
House | 4 bedrooms, high-speed internet

6. Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
Stareway to Heaven in Fairfield
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

7. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
The price is AED 661
AED 837 total
includes taxes & fees
16 Aug - 17 Aug
2-bedroom apartmet No cleaning Fee
Coffee/tea maker, fridge, microwave, oven

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 AED 1,429
AED 3,461 total
includes taxes & fees
23 Aug - 24 Aug
5 minute walk to beach, walk to town & train
Front of property

9. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is AED 2,649
AED 4,332 total
includes taxes & fees
16 Aug - 17 Aug
Beechmont - Perfect for Family Retreat!
1 bedroom, desk, iron/ironing board, WiFi (free)

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 AED 514
AED 852 total
includes taxes & fees
16 Aug - 17 Aug
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Exterior

11. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (158 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is AED 517
AED 595 total
includes taxes & fees
20 Aug - 21 Aug
Stamford Suites
Smart TV

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 AED 1,319
AED 3,603 total
includes taxes & fees
25 Aug - 26 Aug
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Coffee/tea maker, fridge, microwave, oven

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 AED 1,385
AED 2,987 total
includes taxes & fees
23 Aug - 24 Aug
Spacious Retreat with Game Room and Fire Pit
1 bedroom, iron/ironing board, WiFi, bed sheets

14. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is AED 1,131
AED 1,762 total
includes taxes & fees
16 Aug - 17 Aug
Cozy 1-bedroom house in welcoming Bridgeport
Beach nearby, sun loungers, beach towels

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 AED 1,050
AED 2,555 total
includes taxes & fees
31 Aug - 1 Sep
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Interior

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 AED 1,557
AED 3,281 total
includes taxes & fees
18 Aug - 19 Aug
5BR Beach House, Water Views, Game Room, Backyard
TV

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 AED 1,462
AED 2,577 total
includes taxes & fees
26 Aug - 27 Aug
Spacious Stamford Home | Family, Work, Parking
Smart TV

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 AED 529
AED 1,534 total
includes taxes & fees
19 Aug - 20 Aug
Modern Luxe 1BR Apt in Downtown Stamford
Interior

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 AED 507
AED 1,512 total
includes taxes & fees
14 Sep - 15 Sep
Luxury Designer 2 bedroom+office/3bed vacation home.
Coffee/tea maker, fridge, microwave, oven

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 AED 1,456
AED 3,068 total
includes taxes & fees
8 Sep - 9 Sep
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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

8/10 Good
"The only reason I have it 4 stars instead of 5 was because hair was in the bathroom and the ac was giving us trouble. Other than that the staff is amazing and the property exceeded my expectations. I was surprised to see a movie theater on the property and the seats are comfortable and heated and just beautiful, the food was amazing and the seating area is very peaceful, beautiful and with the right person romantic. I will definitely be returning."
Nicole 2-night trip
Posted 6 hours ago
Hyatt Regency Greenwich

Frequently asked questions

Can I find vacation rentals in Westport?

Yes, there are vacation rentals in Westport near Westport Arts Center, or you can choose a more secluded option if you want a relaxing stay. Westport is known for its football games and waterfront. Make sure you have time to check out the entertainment choices and theaters during your trip.

What are some of the best vacation rentals in Westport?

Charming Home in Seaside: This vacation home rental near 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 you can cook with friends or family.

How many vacation rentals will I find in Westport?

Expedia has 55 vacation 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 vacation rental in Westport like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Westport. Vacation rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.