Photo by Marina Timo

Westport Holiday Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
24 Jan - 25 Jan
Tomorrow
25 Jan - 26 Jan
This weekend
24 Jan - 26 Jan
Next weekend
31 Jan - 2 Feb

Holiday Rentals in Westport

Westport Paradise With Every Amenity!
Outdoor pool, a heated pool

Westport Paradise With Every Amenity!

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is HK$3,816
HK$5,555 total
includes taxes & fees
26 Jan - 27 Jan
Westport Paradise With Every Amenity!
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill
Dining

Studio OSM · Sunny Westport Studio Apt. Above Historic Mill

10.0 out of 10, Exceptional, (68)
"We arrived later than the posted check in and Gerard and we spoke on the phone and everything went well. We felt like we were home. The apartment is all that it said in the ad were very accurate. Quaint, cozy and no hotel hassle. The next time we visit we will definitely look for this place!"
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Miscellaneous

Stay 3 Nights or Longer Until January 31 and Get 15% Off

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Stamford Suites
Exterior

Stamford Suites

3.0 star property
6.8 out of 10, (773)
"It was in walking distance of the event we were going to."
The price is HK$983
HK$1,130 total
includes taxes & fees
6 Feb - 7 Feb
Stamford Suites
Business or Weekend escape
Pool

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is HK$584
HK$1,051 total
includes taxes & fees
4 Feb - 5 Feb
Business or Weekend escape
DUNE Fairfield Beach
Private beach nearby, sun-loungers, beach umbrellas, beach towels

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (46)
"Place was clean and comfortable. Some nights were louder than others with by passers from the bar next door. Otherwise pleasant visit. Could not get in the first night. Needed to get another hotel stay. Was not able to reach anyone."
The price is HK$1,688
HK$2,370 total
includes taxes & fees
26 Jan - 27 Jan
DUNE Fairfield Beach
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Terrace/patio

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (116)
"We had a great time staying in this property. It offers more amenities than if staying in a hotel, and at a reduced cost. Communication with owner was excellent, would highly recommend, and would definitely stay again."
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Luxury Designer 2 bedroom+office/3bed vacation home.
Miscellaneous

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

9.6 out of 10, Exceptional, (17)
"The apartment looks just like the photos. It’s totally updated and clean. The host leaves water, coffee and a few snacks which do very sweet. Paul the host responds quickly to any questions you have. I agree with previous reviews it would be nice if all the windows had shades since it’s a busy area. It’s not the greatest area but truly safe and the neighbors were friendly and a few yummy bakery’s in walking distance. Our only surprise was there was no oven just a stove top which limited...
The price is HK$1,153
HK$3,234 total
includes taxes & fees
26 Jan - 27 Jan
Luxury Designer 2 bedroom+office/3bed vacation home.
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Beach nearby, beach towels

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (26)
"Wonderful little bungalow. Owners are really nice and responsive. House is well maintained, cleaned and better stocked than any other rental we've been in. Thank you!!"
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Guesthouse at Norwalk Inn
Private kitchen

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"Great space would be better if there were kuerig cups to go with the machine in the kitchen"
The price is HK$3,694
HK$4,248 total
includes taxes & fees
26 Jan - 27 Jan
Guesthouse at Norwalk Inn
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Point of interest

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

8.6 out of 10, Excellent, (4)
"The location of Ms. Jay's place is unbeatable! My group and I were in town for an event in the Total Mortgage Arena. The drive was 5 minutes max! Ms. Jay is great with communication. She was always available for any questions. The apartment is very homey, cozy and comfortable. Very nicely decorated and it has everything you might need. (We would just recommend some mirrors in the bedrooms). The place is next to a very busy street which there is always a lot of noise, especially at night. One...
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Fridge, microwave, oven, stovetop

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, coffee/tea maker

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (26)
"The house was clean, comfortable, and kitchen was great. Only problem was stairs for my handicapped sister-too steep but possible. Manager very nice"
Cheerful 4 bedrooms residential house.
Beachfront 3-bedroom vacation home just 14 minutes from Yale University
3 bedrooms, desk, WiFi, bed sheets

Beachfront 3-bedroom vacation home just 14 minutes from Yale University

10.0 out of 10, Exceptional, (30)
"House was great for a holiday stay while visiting family nearby. Brad was very responsive with any questions we had. If you like being on the water, this is the spot!"
Beachfront 3-bedroom vacation home just 14 minutes from Yale University
The Safe House - High Tech Apt #2 - 3 Beds
Beach

The Safe House - High Tech Apt #2 - 3 Beds

9.6 out of 10, Exceptional, (35)
"Enjoyed my second stay at the Safe House. Plenty of space, great proximity to Greenwich downtown."
The price is HK$919
HK$1,760 total
includes taxes & fees
23 Feb - 24 Feb
The Safe House - High Tech Apt #2 - 3 Beds
Captain's Cottage - Cold Spring Harbor Water Views
Aerial view

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (53)
"Cute, well-appointed house, great communication, fun stay!"
The price is HK$1,651
HK$3,370 total
includes taxes & fees
4 Feb - 5 Feb
Captain's Cottage - Cold Spring Harbor Water Views
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Interior

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
The Safe House - High Tech Apt #3 - 4 beds
Beach

The Safe House - High Tech Apt #3 - 4 beds

9.8 out of 10, Exceptional, (43)
"The apartment was large and had a well stocked kitchen. The queen sized bed was comfortable and the apartment was quiet with off street parking for two cars. "
The price is HK$787
HK$1,589 total
includes taxes & fees
21 Feb - 22 Feb
The Safe House - High Tech Apt #3 - 4 beds
Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr
Terrace/patio

Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
The price is HK$1,534
HK$2,570 total
includes taxes & fees
25 Jan - 26 Jan
Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr
Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House
Smart TV, Netflix, Hulu, toys

Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House

Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House
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.
Don't see what you're looking for?
See all available properties in Westport
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Westport you may be interested in

Inn at Longshore
Outdoor wedding area

Inn at Longshore

2.5 star property
9.2 out of 10, Wonderful, (137)
"Beautiful Inn"
Inn at Longshore
Westport Paradise With Every Amenity!
Outdoor pool, a heated pool

Westport Paradise With Every Amenity!

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is HK$3,816
HK$5,555 total
includes taxes & fees
26 Jan - 27 Jan
Westport Paradise With Every Amenity!
EVEN Hotel Norwalk, an IHG Hotel
Individually decorated, individually furnished, desk, laptop workspace

EVEN Hotel Norwalk, an IHG Hotel

3.5 star property
8.2 out of 10, Very good, (1005)
"Comfortable beds, clean and modern. "
The price is HK$779
HK$896 total
includes taxes & fees
6 Feb - 7 Feb
EVEN Hotel Norwalk, an IHG Hotel
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.

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?

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center: This holiday home rental outside of Westport is located next to a golf course, and offers a balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 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 51 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. Westport Country Playhouse and Levitt Pavilion 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.