A calm river reflecting buildings and trees, with a clear sky above.

Search Vacation Homes in Westport

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Westport vacation homes

A modern kitchen with white cabinetry, a stainless steel refrigerator, a dishwasher, and a microwave.

1. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is ￥54,538
￥100,539 total
includes taxes & fees
Oct 18 - Oct 19
Gilded Age Luxury Surrounded by Nature
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

2. 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, (15 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 ￥45,127
￥107,377 total
includes taxes & fees
Nov 9 - Nov 10
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

3. 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 ￥34,043
￥92,146 total
includes taxes & fees
Nov 3 - Nov 4
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A swimming pool at night with blue lighting.

4. 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 ￥14,227
￥24,067 total
includes taxes & fees
Oct 26 - Oct 27
Business or Weekend escape
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

5. 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
6.6 out of 10, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is ￥24,898
￥41,991 total
includes taxes & fees
Oct 22 - Oct 23
Centric property close to all the great things in the city
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

6. Elite room stay

Elite room stay
Bridgeport
The price is ￥32,723
￥54,072 total
includes taxes & fees
Oct 16 - Oct 17
Elite room stay
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

7. 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)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
The price is ￥43,227
￥103,024 total
includes taxes & fees
Nov 9 - Nov 10
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

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

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.4 out of 10, Exceptional, (20 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
The price is ￥63,083
￥131,527 total
includes taxes & fees
Oct 21 - Oct 22
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A white room with a round table, two benches, and a window with a view of houses.

9. Stay at Black Rock Harbor

Stay at Black Rock Harbor
Black Rock Historic District
10.0 out of 10, Exceptional, (29 reviews)
"This house was perfect for our family. Will definitely use again when we're visiting family in the area."
United States
Laura L.
The price is ￥70,145
￥147,486 total
includes taxes & fees
Nov 1 - Nov 2
Stay at Black Rock Harbor
A modern kitchen with white cabinets, a marble island, and black bar stools.

10. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay."
United States
Linda S.
The price is ￥55,102
￥119,640 total
includes taxes & fees
Nov 5 - Nov 6
Spacious Retreat with Game Room and Fire Pit
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

11. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
10.0 out of 10, Exceptional, (1 review)
"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."
United States
Raelyn O.
The price is ￥82,202
￥145,932 total
includes taxes & fees
Nov 15 - Nov 16
4 Mi to Beach & Dtwn! Charming Fairfield Home
A bedroom with a bed, a nightstand, a dresser, a window with blinds, and a radiator.

12. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (21 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is ￥35,449
￥82,190 total
includes taxes & fees
Oct 27 - Oct 28
Gem by the water+ firepit and all fenced backyard
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

13. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is ￥30,035
￥58,568 total
includes taxes & fees
Nov 15 - Nov 16
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A living room with a sofa set, a coffee table, and a television on a stand.

14. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is ￥47,977
￥94,284 total
includes taxes & fees
Oct 16 - Oct 17
Spacious Stamford Home | Family, Work, Parking
A two-story house with a porch, stone steps, and a variety of plants.

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

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
8.8 out of 10, Excellent, (10 reviews)
"Plenty of bedrooms and space for the family. Very prompt communication with host."
United States
David K.
The price is ￥102,578
￥202,143 total
includes taxes & fees
Oct 20 - Oct 21
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

16. 5BR Beach House, Water Views, Steps to Beach, Backyard

5BR Beach House, Water Views, Steps to Beach, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"The property was amazing. The house was clean, beautiful, and well equipped. Plenty of space yet still cozy. Host was very communicative and gracious, had a pleasant experience and will definitely be back!"
United States
Maxx V.
The price is ￥77,112
￥153,863 total
includes taxes & fees
Oct 20 - Oct 21
5BR Beach House, Water Views, Steps to Beach, Backyard
A bedroom with a bed, two bedside tables, a lamp, an air conditioning unit, a patterned rug, and a painting on the wall.

17. Renovated Beachside Retreat

Renovated Beachside Retreat
Milford
The price is ￥17,892
￥62,536 total
includes taxes & fees
Nov 5 - Nov 6
Renovated Beachside Retreat
A modern living room with a white sofa, a glass coffee table, and a piano.

18. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.2 out of 10, Wonderful, (9 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is ￥58,173
￥109,343 total
includes taxes & fees
Oct 28 - Oct 29
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A bedroom with two beds, a wooden dresser, and a mirror.

19. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is ￥48,657
￥75,360 total
includes taxes & fees
Oct 17 - Oct 18
Cozy 1-bedroom house in welcoming Bridgeport
Open concept kitchen

20. 5BR Beach House, Game Room + Huge Backyard

5BR Beach House, Game Room + Huge Backyard
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (26 reviews)
"Very spacious and nicely decorated"
United States
Linda M.
The price is ￥73,628
￥157,228 total
includes taxes & fees
Oct 18 - Oct 19
5BR Beach House, Game Room + Huge Backyard
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Westport Hotel Reviews

The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

8/10 Good
"The front desk"
Robert 1-night trip
Posted 21 hours ago
The Armon Stamford Hotel & Conference

Find out more about Westport

Westport Vacation Homes information

Number of reviews
313
Accommodation
270 Vacation Homes
Lowest Price
￥24,067
Highest Price
￥202,143