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

Westport Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Westport holiday rentals

A bedroom with a large bed, bedside lamps, a mirror, and a potted plant.

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 HK$1,129
HK$2,044 total
includes taxes & fees
27 Sept - 28 Sept
Spacious Studio with Pool Table
A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

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

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.2 out of 10, Wonderful, (17 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
Nama-stay, sweet pink Saugatuck Shores beach cottage
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

3. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is HK$1,392
HK$2,079 total
includes taxes & fees
26 Oct - 27 Oct
DUNE Fairfield Beach
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.

4. 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, (18 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
The price is HK$1,098
HK$1,804 total
includes taxes & fees
27 Sept - 28 Sept
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

5. 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 HK$2,815
HK$3,238 total
includes taxes & fees
29 Sept - 30 Sept
Guesthouse at Norwalk Inn
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

6. 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, (27 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveller
The price is HK$1,161
HK$3,311 total
includes taxes & fees
28 Sept - 29 Sept
Luxury Designer 2 bedroom+office/3bed vacation home.
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

7. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (5 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.
The price is HK$1,057
HK$2,602 total
includes taxes & fees
27 Sept - 28 Sept
Modern 2 Bed in BlackRock
A covered outdoor seating area with wicker sofas, a fire pit, and string lights.

8. 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.
The price is HK$1,353
HK$2,952 total
includes taxes & fees
28 Sept - 29 Sept
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
A modern kitchen with white cabinetry, a granite countertop, and a built-in island with bar stools.

9. Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
7.4 out of 10, Good, (3 reviews)
"Our host forgot we were coming, did not have check-in instructions or access, and did not respond to message or phone call. We had reserved this property to move my daughter across the country and into her dorm in college. Needless to say, an already stressful time was made more stressful as we had to find somewhere new to stay that evening that did not offer the same amenities we had planned on. Very disappointed and made for a rough start to our trip. I was pleased we received a full refund."
United States
Sarah K.
The price is HK$1,059
HK$2,310 total
includes taxes & fees
28 Sept - 29 Sept
Zen, Spacious & Comfy 2 bed, Lux beds
A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

10. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is HK$1,835
HK$3,350 total
includes taxes & fees
28 Sept - 29 Sept
Gilded Age Luxury Surrounded by Nature
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

11. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is HK$1,235
HK$2,020 total
includes taxes & fees
26 Sept - 27 Sept
Centric property close to all the great things in the city
A modern kitchen with a white refrigerator, a stove, and a sink. There are four wicker chairs around a white table.

12. Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveller
The price is HK$1,045
HK$2,558 total
includes taxes & fees
6 Oct - 7 Oct
Renovated 2BR Retreat / Modern Comforts Included
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

13. 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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is HK$1,757
HK$4,661 total
includes taxes & fees
21 Oct - 22 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

14. Elite room stay

Elite room stay
Bridgeport
The price is HK$1,623
HK$2,604 total
includes taxes & fees
26 Sept - 27 Sept
Elite room stay
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

15. 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 HK$2,502
HK$5,704 total
includes taxes & fees
19 Oct - 20 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A room with a large arched window, a bed, a bedside table, a lamp, and a potted plant.

16. Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (8 reviews)
"The Orange & Groovy Apt. was as described. All the amenities we needed and we had a lovely time and enjoyed the area. Will book again!"
United States
Betty W.
The price is HK$1,098
HK$1,820 total
includes taxes & fees
28 Sept - 29 Sept
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk
A modern living room with a large window, a sofa, a coffee table, and a TV.

17. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
9.6 out of 10, Exceptional, (12 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is HK$863
HK$1,518 total
includes taxes & fees
28 Sept - 29 Sept
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
A swimming pool at night with blue lighting.

18. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is HK$706
HK$1,194 total
includes taxes & fees
5 Oct - 6 Oct
Business or Weekend escape
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with a kettle, and a painting on the wall.

19. 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, (4 reviews)
"Nice place to stay "
United States
Maria Elena G.
The price is HK$1,592
HK$3,438 total
includes taxes & fees
19 Oct - 20 Oct
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

20. 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 HK$2,345
HK$3,034 total
includes taxes & fees
26 Oct - 27 Oct
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
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

Ethan Allen Hotel

Ethan Allen Hotel

10/10 Excellent
"The hotel is situated in a very beautiful area. Conveniently located to the mall and other attractions. Rooms were clean and comfortable. Breakfast at the restaurant was also quite nice."
Analice 3-night trip
Posted 1 hour ago
Ethan Allen Hotel

Find out more about Westport

Search for holiday rentals in Westport on Expedia! You can easily find your home rentals, villas, holiday apartments in Westport using one of the methods below:

  • View our selection of featured holiday rentals in Westport
  • Use the map to find apartments and other holiday homes in the Westport neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Westport while they last

Look no further and take a look at our great range of rental properties in Westport!

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?

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends: This holiday home rental outside of Westport is located on the beach, and has a balcony, a selection of games and a BBQ 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 that you can cook with friends or family.

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.