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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Westport vacation rentals

A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

1. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (19 reviews)
"A sweet get away for which the highlights included a breezy screened porch and sensational walks right from the property. Easy shopping and neighbors right out of central casting who provided additional restaurant suggestions and general warmth. Would stay here again in a heart beat. We were here for a week and were sad to leave."
United States
Mel O.
The price is AED 826
AED 1,627 total
includes taxes & fees
16 Nov - 17 Nov
Nama-stay, sweet pink Saugatuck Shores beach cottage
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is AED 1,146
AED 1,317 total
includes taxes & fees
1 Dec - 2 Dec
Guesthouse at Norwalk Inn
A modern bathroom with a white vanity, a large mirror, a shower with a striped curtain, and a wooden floor.

3. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (119 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is AED 647
AED 968 total
includes taxes & fees
16 Dec - 17 Dec
DUNE Fairfield Beach
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a built-in oven.

4. 3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ

3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
Cranbury
8.8 out of 10, Excellent, (8 reviews)
"Great spot for our family. "
United States
Kevin I.
The price is AED 1,084
AED 2,150 total
includes taxes & fees
19 Nov - 20 Nov
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

5. 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, (16 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 962
AED 2,352 total
includes taxes & fees
17 Nov - 18 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

6. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (210 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
The price is AED 540
AED 621 total
includes taxes & fees
18 Nov - 19 Nov
Stamford Suites
A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

7. 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 1,098
AED 1,355 total
includes taxes & fees
16 Nov - 17 Nov
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

8. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is AED 819
AED 1,487 total
includes taxes & fees
18 Nov - 19 Nov
Gilded Age Luxury Surrounded by Nature
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

9. 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, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is AED 734
AED 2,015 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern kitchen with a large island, wooden cabinets, and pendant lighting.

10. Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is AED 2,631
AED 3,971 total
includes taxes & fees
24 Nov - 25 Nov
Stareway to Heaven in Fairfield
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

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

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (29 reviews)
"Great location and clean property. Some items were broken or missing, but overall, a nice stay."
United States
Cherie
The price is AED 617
AED 1,576 total
includes taxes & fees
23 Nov - 24 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.
A covered outdoor seating area with wicker sofas, a fire pit, and string lights.

12. Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (2 reviews)
"Host was attentive and the space was comfortable and exactly what we needed"
United States
Parker M.
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
A living room with a blue sofa, a black leather chair, a blue rug, and a door with a 'HOME' sign.

13. Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay "
United States
Maria Elena G.
The price is AED 725
AED 1,469 total
includes taxes & fees
14 Dec - 15 Dec
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

14. 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
9.4 out of 10, Exceptional, (19 reviews)
"A hidden gem! We have stayed here twice now when attending concerts at Hartford Healthcare Amphitheater. A beautifully appointed room within walking distance to the shows!"
United States
Kim F.
The price is AED 514
AED 815 total
includes taxes & fees
16 Nov - 17 Nov
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A modern living room with a sofa, coffee table, and a bed in the background.

15. Renovated 3BR Apt / Easy Check-In / FamilyFriendly

Renovated 3BR Apt / Easy Check-In / FamilyFriendly
West End - West Side
10.0 out of 10, Exceptional, (1 review)
"Unit was clean, beds were large and comfy. Very close to downtown. Would stay again!"
United States
Matthew
The price is AED 508
AED 1,260 total
includes taxes & fees
16 Nov - 17 Nov
Renovated 3BR Apt / Easy Check-In / FamilyFriendly
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

16. 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, (19 reviews)
"Beautiful home, clean and exactly as described.We loved our stay and plan on returning.The host was wonderful to work with.An overall excellent experience."
United States
Tara C.
The price is AED 1,021
AED 2,360 total
includes taxes & fees
7 Dec - 8 Dec
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

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

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.6 out of 10, Exceptional, (22 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 1,382
AED 2,833 total
includes taxes & fees
18 Nov - 19 Nov
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A modern kitchen with white cabinets, a marble island, and black bar stools.

18. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
8.6 out of 10, Excellent, (4 reviews)
"We had a wonderful stay."
United States
Linda S.
The price is AED 1,299
AED 2,769 total
includes taxes & fees
18 Nov - 19 Nov
Spacious Retreat with Game Room and Fire Pit
Private kitchen

19. The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry

The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (1 review)
"."
United States
Matthew R.
The price is AED 508
AED 1,260 total
includes taxes & fees
16 Nov - 17 Nov
The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

20. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
8.0 out of 10, Very good, (7 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
Modern 2 Bed in BlackRock
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

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"Beautiful and close to great restaurants and shopping, friendly style comfortable room"
Tawni 1-night trip
Posted 4 hours ago
Norwalk Inn & Conference Center

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?

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends: This vacation home rental near Westport is located on the beach and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. 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 54 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.