Photo by Marina Timo

Search Vacation Homes in Westport

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Westport vacation homes

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Shelton
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is AED 441
AED 723 total
includes taxes & fees
18 Dec - 19 Dec
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Newly renovated Private bedroom near Stony Brook University

2.0 star property
Stony Brook
8.0 out of 10, Very Good, (2)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
Newly renovated Private bedroom near Stony Brook University

The ARLO - Walk to Brewery and Restaurants

Milford
9.4 out of 10, Exceptional, (3)
"Very nice house....loved the front enclosed porch, and the kitchen was amazing with everything we needed. The deck with the Blackstone Grill was a great place to sit and relax. We enjoyed many of the nearby restaurants too. Matt and Jess were great hosts!J&J, Mooresville, NC"
United States
Jena
The ARLO - Walk to Brewery and Restaurants

Business or Weekend escape

Stratford
9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AED 312
AED 538 total
includes taxes & fees
6 Jan - 7 January 2026
Business or Weekend escape

Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

Fairfield
10.0 out of 10, Exceptional, (22)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC

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

Greenwich
9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
The price is AED 471
AED 979 total
includes taxes & fees
11 Dec - 12 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

#37 - Luxury Collection

2.0 star property
Stratford
8.0 out of 10, Very Good, (4)
"We enjoyed the coziest getaway at this property. Newly renovated, clean and tucked away without being accessible to local attractions. "
United States
Sarah T.
The price is AED 546
AED 1,425 total
includes taxes & fees
15 Dec - 16 Dec
#37 - Luxury Collection

Marine Theme - 4 BR - Backyard - Fire pit

North End
9.8 out of 10, Exceptional, (8)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is AED 588
AED 1,527 total
includes taxes & fees
16 Dec - 17 Dec
Marine Theme - 4 BR - Backyard - Fire pit

Bright Escape, Top-Rated Design, Fire pit, Near Beach

Fairfield
10.0 out of 10, Exceptional, (11)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
Bright Escape, Top-Rated Design, Fire pit, Near Beach

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
The price is AED 1,139
AED 2,232 total
includes taxes & fees
5 Jan - 6 January 2026
Captain's Cottage - Cold Spring Harbor Water Views

Stylish 2BR House Near Stony Brook University and shopping, fully renovated

2.0 star property
Stony Brook
10.0 out of 10, Exceptional, (1)
"perfect place"
New Zealand
Akaki G.
The price is AED 843
AED 1,953 total
includes taxes & fees
20 Dec - 21 Dec
Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside
9.8 out of 10, Exceptional, (9)
"Lovely little home in Stamford."
United States
Pat A.
The price is AED 578
AED 1,209 total
includes taxes & fees
11 Dec - 12 Dec
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

The B&W Haven 5BR Home with yard theater + Office

Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (8)
"Host was very polite and communicated well throughout the stay. The property appears well maintained. There are window units but everyone was comfortable for the duration of our stay."
United States
George M.
The price is AED 1,051
AED 2,469 total
includes taxes & fees
11 Dec - 12 Dec
The B&W Haven 5BR Home with yard theater + Office

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

2.0 star property
Shelton
The price is AED 336
AED 1,422 total
includes taxes & fees
12 Dec - 13 Dec
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Fairfield
9.4 out of 10, Exceptional, (20)
"Very nice house and location. Very good service and excellent attention."
Mexico
Armando V.
The price is AED 1,190
AED 2,726 total
includes taxes & fees
11 Dec - 12 Dec
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

North End
9.4 out of 10, Exceptional, (6)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
United States
April R.
The price is AED 3,223
AED 5,827 total
includes taxes & fees
11 Dec - 12 Dec
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Modern + Spacious 5BR/2BA Home, Renovated Backyard

West End - West Side
9.6 out of 10, Exceptional, (4)
"Used for family weekend at SHU. Convenient location and plenty of space for the whole family! "
United States
Laurene S.
The price is AED 1,305
AED 2,840 total
includes taxes & fees
11 Dec - 12 Dec
Modern + Spacious 5BR/2BA Home, Renovated Backyard

Cozy cute Relaxing home

Southbury
8.8 out of 10, Excellent, (6)
"nice quiet area"
United States
Alex V.
The price is AED 661
AED 1,223 total
includes taxes & fees
31 Dec - 1 January 2026
Cozy cute Relaxing home

Beechmont - Perfect for Family Retreat!

5.0 star property
North End
The price is AED 3,108
AED 4,860 total
includes taxes & fees
12 Dec - 13 Dec
Beechmont - Perfect for Family Retreat!

Country Retreat | Heated Saltwater Pool | BBQ | Fire Pit

Redding
10.0 out of 10, Exceptional, (2)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is AED 889
AED 2,221 total
includes taxes & fees
6 Jan - 7 January 2026
Country Retreat | Heated Saltwater Pool | BBQ | Fire Pit
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