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Westport Holiday Rentals

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Holiday Rentals in Westport

Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

The price is NZ$4,058
includes taxes & fees
15 July - 16 July
Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

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

The price is NZ$328
includes taxes & fees
20 July - 21 July
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Business or Weekend escape

9.2 out of 10, Wonderful, (40)
"Very nice owner with great communication. "
The price is NZ$244
includes taxes & fees
20 July - 21 July
Business or Weekend escape

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

8.4 out of 10, Very good, (5)
The price is NZ$424
includes taxes & fees
21 July - 22 July
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Centric property close to all the great things in the city

8.0 out of 10, Very good, (11)
"This rental was great accommodation"
The price is NZ$500
includes taxes & fees
20 July - 21 July
Centric property close to all the great things in the city

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (3)
"The house was exactly as presented on the website. 4 good size bedrooms, all with very comfortable king size beds, that is typically hard to find! Fantastic sunlit kitchen nook. Good location, easy access to I-95 and Parkway. "
The price is NZ$1,034
includes taxes & fees
16 July - 17 July
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Cozy cute Relaxing home

8.6 out of 10, Excellent, (4)
"nice quiet area"
The price is NZ$525
includes taxes & fees
25 July - 26 July
Cozy cute Relaxing home

My little place Cozy Open concept for quiet time.

8.0 out of 10, Very good, (2)
"Great, clean property that was easy to access and very convenient to downtown Bridgeport. Perfect place to clean up and sleep. Very welcoming space."
The price is NZ$816
includes taxes & fees
16 July - 17 July
My little place Cozy Open concept for quiet time.

Marine Theme - 4 BR - Backyard - Fire pit

9.8 out of 10, Exceptional, (6)
"Had a great stay at Sarah’s place. She was very communicative and helpful before and during our stay. The house was nice and large - it was great having two living rooms for our large group. Convenient location close to many stores and sights!"
The price is NZ$827
includes taxes & fees
22 July - 23 July
Marine Theme - 4 BR - Backyard - Fire pit

The Luxury downtown. Pool Jim basketball

The price is NZ$431
includes taxes & fees
20 July - 21 July
The Luxury downtown. Pool Jim basketball

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Lovely little home in Stamford."
The price is NZ$751
includes taxes & fees
17 July - 18 July
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (7)
"The water just steps from the front door was beautiful and enticing. Being able to carry our kayak & SUP just across the street for some time on the water was a dream. The entire neighborhood was quiet and everyone was friendly. But it's not just the location. The apartment itself is beautiful, very comfortable, and a joy to visit. I actually did nap on the sleeping porch one day! Spent too much time with coffee in the front porch enjoying the view. Best bed in a VRBO we ever slept in. And,...
The price is NZ$977
includes taxes & fees
22 July - 23 July
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC

10.0 out of 10, Exceptional, (6)
"And the bed was confortable"
The price is NZ$1,127
includes taxes & fees
20 July - 21 July
Bright Escape, Top-Rated Design, Fire pit, Near Beach, 90 minutes to NYC

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

10.0 out of 10, Exceptional, (3)
"Great space! Very clean & well appointed! If you forgot to pack it, it is probably there!"
The price is NZ$804
includes taxes & fees
29 July - 30 July
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Updated, cozy single family in Fairfield County

9.4 out of 10, Exceptional, (11)
"House was great, hosts were attentive. Enjoyed our stay"
Updated, cozy single family in Fairfield County

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

9.0 out of 10, Wonderful, (2)
"the home was nice clean if in the area I would stay here again"
The price is NZ$922
includes taxes & fees
22 July - 23 July
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Charming Long Island Family Getaway with Pool. An hour from Hamptons

7.6 out of 10, Good, (7)
"Had a great time here. The house was clean and well maintained. The host communicated with us often and overall it was a great stay!"
The price is NZ$2,492
includes taxes & fees
11 Aug - 12 Aug
Charming Long Island Family Getaway with Pool. An hour from Hamptons

Charming 2-bedroom house with WiFi, AC in Fairfield

7.0 out of 10, Good, (2)
"Amalfi’s place was as described. It was clean and comfortable and mostly quiet. Amalfi was excellent with communication. Would certainly stay again when visiting family."
The price is NZ$575
includes taxes & fees
23 July - 24 July
Charming 2-bedroom house with WiFi, AC in Fairfield

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

9.2 out of 10, Wonderful, (5)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
The price is NZ$1,056
includes taxes & fees
18 July - 19 July
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (62)
"Great home to stay. Beautiful area to explore!"
The price is NZ$1,120
includes taxes & fees
16 July - 17 July
Captain's Cottage - Cold Spring Harbor Water Views
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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Frequently asked questions

Can I find holiday rentals in Westport?

Yes, there are holiday rentals in Westport close to Earthplace Museum, 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?

Main Street Westport, walk to shops, dining, downtown: This highly rated holiday home rental in Westport is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a fridge, a microwave and a coffee maker, 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 Old Mill Beach and Compo 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.