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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Westport vacation homes

A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

1. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is ￥36,949
￥67,439 total
includes taxes & fees
Oct 19 - Oct 20
Gilded Age Luxury Surrounded by Nature
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

2. 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 ￥34,264
￥92,095 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

3. 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 ￥44,686
￥106,715 total
includes taxes & fees
Nov 9 - Nov 10
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

4. 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 ￥24,869
￥42,259 total
includes taxes & fees
Oct 11 - Oct 12
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.

5. Elite room stay

Elite room stay
Bridgeport
The price is ￥32,685
￥54,325 total
includes taxes & fees
Oct 12 - Oct 13
Elite room stay
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

6. 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 ￥37,896
￥96,745 total
includes taxes & fees
Nov 9 - Nov 10
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A swimming pool at night with blue lighting.

7. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is ￥14,211
￥24,040 total
includes taxes & fees
Oct 11 - Oct 12
Business or Weekend escape
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 ￥61,051
￥128,906 total
includes taxes & fees
Nov 2 - Nov 3
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A modern kitchen with white cabinets, a marble island, and black bar stools.

9. 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 ￥60,160
￥127,353 total
includes taxes & fees
Oct 28 - Oct 29
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.

10. 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 ￥82,108
￥146,397 total
includes taxes & fees
Oct 25 - Oct 26
4 Mi to Beach & Dtwn! Charming Fairfield Home
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

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

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (20 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is ￥24,885
￥51,371 total
includes taxes & fees
Oct 13 - Oct 14
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

12. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
The price is ￥45,188
￥113,318 total
includes taxes & fees
Oct 14 - Oct 15
5BR Beach Home | Walk to Cove Beach + Private Yard
A campfire with a wooden table and benches by a 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 ￥27,001
￥55,052 total
includes taxes & fees
Oct 12 - Oct 13
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A two-story house with a porch, stone steps, and a variety of plants.

14. 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 ￥104,090
￥206,051 total
includes taxes & fees
Oct 12 - Oct 13
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A living room with a sofa set, a coffee table, and a television on a stand.

15. 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 price is ￥51,791
￥99,035 total
includes taxes & fees
Oct 14 - Oct 15
Spacious Stamford Home | Family, Work, Parking
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 ￥70,310
￥144,480 total
includes taxes & fees
Oct 14 - Oct 15
5BR Beach House, Water Views, Steps to Beach, Backyard
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

17. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is ￥152,042
￥230,113 total
includes taxes & fees
Oct 11 - Oct 12
Beechmont - Perfect for Family Retreat!
Open concept kitchen

18. 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 ￥82,318
￥168,853 total
includes taxes & fees
Oct 14 - Oct 15
5BR Beach House, Game Room + Huge Backyard
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 ￥48,602
￥75,274 total
includes taxes & fees
Oct 16 - Oct 17
Cozy 1-bedroom house in welcoming Bridgeport
A modern living room with a white sofa, a glass coffee table, and a piano.

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

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.4 out of 10, Exceptional, (8 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 ￥52,140
￥100,962 total
includes taxes & fees
Oct 28 - Oct 29
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
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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Top Westport Hotel Reviews

Delamar Westport

Delamar Westport

10/10 Excellent
"Great location! The staff was extremely helpful and courteous. Our room was very spacious and the bed comfortable. The bathroom was big with the best shower head, the products they provide are premium!!!⭐️⭐️⭐️⭐️⭐️"
Daniela 1-night trip
Posted 10 hours ago
Delamar Westport

Find out more about Westport

Westport Vacation Homes information

Number of reviews
299
Accommodation
283 Vacation Homes
Lowest Price
￥24,040
Highest Price
￥230,113