Photo by Marina Timo

Search Vacation Homes in Westport

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Westport

Business or Weekend escape

9.2 out of 10, Wonderful, (40)
"Very nice owner with great communication. "
The price is AED 312
AED 538 total
includes taxes & fees
20 Jul - 21 Jul
Business or Weekend escape

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

8.8 out of 10, Excellent, (6)
The price is AED 393
AED 889 total
includes taxes & fees
21 Jul - 22 Jul
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (5)
"Very nice place."
Minutes to Walnut Beach, newly renovated 3 bedroom home

Charming 3-bedroom house with WiFi, AC in serene Fairfield

10.0 out of 10, Exceptional, (3)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (12)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

Bright Milford Beach House w/ Outdoor Shower

9.2 out of 10, Wonderful, (10)
"We had the best time! It was clean, good location, and the owner was wonderful! We even got to go the beach in December! We would definitely rent this place again!!"
Bright Milford Beach House w/ Outdoor Shower

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 AED 545
AED 1,277 total
includes taxes & fees
23 Jul - 24 Jul
Charming 2-bedroom house with WiFi, AC in Fairfield

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

9.8 out of 10, Exceptional, (10)
"5 Star stay!"
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is AED 1,341
AED 2,599 total
includes taxes & fees
30 Jul - 31 Jul
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Quaint duplex with private yard. Walk to beach, dining, & shopping!

10.0 out of 10, Exceptional, (43)
"Needed a place to stay with our dog while visiting our granddaughters in a nearby town."
Quaint duplex with private yard. Walk to beach, dining, & shopping!

Main Street Westport, walk to shops, dining, downtown

9.0 out of 10, Wonderful, (2)
"Beautiful home, great location, communicative hosts…A"
Main Street Westport, walk to shops, dining, downtown

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

10.0 out of 10, Exceptional, (4)
"Beautiful house to stay, perfect location to beach and the host Robert was wonderful! Will be staying here again on our next visit. "
The price is AED 1,462
AED 2,636 total
includes taxes & fees
28 Jul - 29 Jul
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

St Julian's Place - Large updated Apt @ 40 Min NYC

10.0 out of 10, Exceptional, (35)
"This is the 3rd time we've stayed here. The apartment looks great and is convenient for us to visit family. We always enjoy staying here."
St Julian's Place - Large updated Apt @ 40 Min NYC

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

8.6 out of 10, Excellent, (7)
"I rented this place because of the location and convenience to the many things we enjoy about Milford CT. The master bedroom is top-notch as well as the living space downstairs. We hoped to use the outdoor fire place make smores, but due to a medical emergency our trip was cut short. Regardless, we enjoyed our stay at 42 Wood Ave. Thank you, Tiffany, for supplying an awesome rental."
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

3-bedroom house in pleasant Norwalk with Pool, outdoor BBQ, and so much more

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. "
3-bedroom house in pleasant Norwalk with Pool, outdoor BBQ, and so much more

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 AED 579
AED 1,103 total
includes taxes & fees
20 Jul - 21 Jul
Centric property close to all the great things in the city

Blue Cottage East Setauket

Blue Cottage East Setauket

Beautiful historic home in Stony Brook!

2.0 star property
8.0 out of 10, Very Good, (10)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

Dulce La Donna by the beach

10.0 out of 10, Exceptional, (1)
"The owner is extremely welcoming and communicates very well. "
Dulce La Donna by the beach
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Westport Hotel Reviews