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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 holiday rentals

A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large 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 £182
includes taxes & fees
8 Dec - 9 Dec
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
9.4 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 £403
includes taxes & fees
11 Nov - 12 Nov
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, (118 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is £197
includes taxes & fees
10 Dec - 11 Dec
DUNE Fairfield Beach
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

4. 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 £263
includes taxes & fees
12 Nov - 13 Nov
Guesthouse at Norwalk Inn
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a built-in oven.

5. 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 £434
includes taxes & fees
10 Nov - 11 Nov
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

6. 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.
The price is £267
includes taxes & fees
29 Nov - 30 Nov
Modern 2 Bed in BlackRock
A covered outdoor seating area with wicker sofas, a fire pit, and string lights.

7. 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 £252
includes taxes & fees
10 Nov - 11 Nov
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

8. 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 £446
includes taxes & fees
10 Nov - 11 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
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.

9. 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 £168
includes taxes & fees
16 Nov - 17 Nov
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

10. 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 £407
includes taxes & fees
10 Nov - 11 Nov
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern kitchen with a white refrigerator, a stove, and a sink. There are four wicker chairs around a white table.

11. 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 £226
includes taxes & fees
30 Nov - 1 Dec
Renovated 2BR Retreat / Modern Comforts Included
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with a kettle, and a painting on the wall.

12. 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 £299
includes taxes & fees
18 Nov - 19 Nov
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

13. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is £416
includes taxes & fees
10 Nov - 11 Nov
Gilded Age Luxury Surrounded by Nature
A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

14. 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 £278
includes taxes & fees
10 Nov - 11 Nov
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

15. 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 £303
includes taxes & fees
16 Nov - 17 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.
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 £407
includes taxes & fees
10 Nov - 11 Nov
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A swimming pool at night with blue lighting.

17. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is £110
includes taxes & fees
11 Nov - 12 Nov
Business or Weekend escape
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

18. 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
6.8 out of 10, (18 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is £194
includes taxes & fees
18 Nov - 19 Nov
Centric property close to all the great things in the city
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

19. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (208 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
The price is £141
includes taxes & fees
10 Nov - 11 Nov
Stamford Suites
Private kitchen

20. 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 £256
includes taxes & fees
10 Nov - 11 Nov
The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
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

A buffet bar with various food items and a selection of liquor bottles in the background.
Delamar Westport

Delamar Westport

Delamar Westport
Westport

10/10 Excellent

Super
United Kingdom
Darron
Reviewed November 7, 2026
Delamar Westport

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, apart-hotels, 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 favorite 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 depends 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 £141 per night. Entering your travel dates in the search wizard you might find 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.

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.