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

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Westport vacation homes

A modern kitchen with white cabinets, a granite countertop, stainless steel appliances, and a large island.

1. Spacious Family Home

Spacious Family Home
Westport
10.0 out of 10, Exceptional, (1 review)
"We had a getaway weekend for a close friend group from college. This location could not have been better! We had everything we needed. Four bedrooms and three full bathrooms and across the street, a bakery, pizza place, fantastically stocked market, and a nice restaurant! A short drive allowed us to enjoy shopping and more food choices, as well as giving our Manhattan friend easy access to the train. Really could not have been a better place for us. Communication with the host was timely,...
United States
Laura B.
The price is ￥71,528
￥143,850 total
includes taxes & fees
Aug 25 - Aug 26
Spacious Family Home
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 ￥43,635
￥107,786 total
includes taxes & fees
Aug 23 - Aug 24
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

3. Elite room stay

Elite room stay
Bridgeport
The price is ￥32,903
￥54,846 total
includes taxes & fees
Aug 23 - Aug 24
Elite room stay
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

4. 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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is ￥37,194
￥97,086 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
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
6.8 out of 10, (16 reviews)
"Having a microwave would also help with the amenities. Overall good. "
United States
Karen A.
The price is ￥25,035
￥42,699 total
includes taxes & fees
Aug 23 - Aug 24
Centric property close to all the great things in the city
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, (17 reviews)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is ￥32,903
￥91,516 total
includes taxes & fees
Aug 24 - Aug 25
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 ￥14,306
￥24,201 total
includes taxes & fees
Sep 13 - Sep 14
Business or Weekend escape
A modern kitchen with a blue accent island, a round dining table, and large windows.

8. 5 minute walk to beach, walk to town & train

5 minute walk to beach, walk to town & train
Fairfield Beach
10.0 out of 10, Exceptional, (26 reviews)
"Host was great. Had a great stay. "
United States
jeff d.
The price is ￥58,740
￥145,754 total
includes taxes & fees
Aug 23 - Aug 24
5 minute walk to beach, walk to town & train
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
10.0 out of 10, Exceptional, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
The price is ￥48,639
￥114,172 total
includes taxes & fees
Sep 16 - Sep 17
Spacious Retreat with Game Room and Fire Pit
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

10. 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 ￥63,005
￥131,668 total
includes taxes & fees
Sep 8 - Sep 9
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
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, (18 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥33,697
￥64,184 total
includes taxes & fees
Sep 15 - Sep 16
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A swimming pool with a stone wall and greenery, a covered patio with outdoor furniture, and a stone building with a tiled roof.

12. Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability

Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability
New Canaan
10.0 out of 10, Exceptional, (42 reviews)
"Unique home with beautiful grounds and classically designed interior. Perfect for relaxing and enjoying with family/friends."
United States
David
The price is ￥207,430
￥345,200 total
includes taxes & fees
Sep 8 - Sep 9
Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

13. 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 ￥60,878
￥119,944 total
includes taxes & fees
Aug 23 - Aug 24
4 Mi to Beach & Dtwn! Charming Fairfield Home
A campfire with a wooden table and benches by a lake.

14. 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, (42 reviews)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
The price is ￥33,618
￥59,961 total
includes taxes & fees
Sep 21 - Sep 22
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

15. 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)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
United States
Erin D.
The price is ￥86,946
￥166,397 total
includes taxes & fees
Aug 25 - Aug 26
5BR Beach Home | Walk to Cove Beach + Private Yard
A bedroom with two beds, a wooden dresser, and a mirror.

16. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is ￥48,925
￥76,252 total
includes taxes & fees
Aug 25 - Aug 26
Cozy 1-bedroom house in welcoming Bridgeport
A two-story house with a porch, stone steps, and a variety of plants.

17. 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 ￥99,423
￥200,409 total
includes taxes & fees
Aug 25 - Aug 26
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

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, (25 reviews)
"Great stay!"
United States
Kyra S.
The price is ￥64,693
￥148,150 total
includes taxes & fees
Aug 24 - Aug 25
5BR Beach House, Game Room + Huge Backyard
A living room with a sofa set, a coffee table, and a television on a stand.

19. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (8 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is ￥48,003
￥94,941 total
includes taxes & fees
Aug 23 - Aug 24
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.

20. 5BR Beach House, Water Views, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is ￥76,937
￥153,781 total
includes taxes & fees
Aug 26 - Aug 27
5BR Beach House, Water Views, Game Room, 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.
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Top Westport Hotel Reviews

Ethan Allen Hotel

Ethan Allen Hotel

10/10 Excellent
"The Ethan Allen hotel is absolutely beautiful. Rooms are clean and spacious. The staff are friendly and welcoming. Grounds are beautifully manicured and the pool is well kept. Conveniently located near the mall. Would highly recommend this hotel."
Lori 2-night trip
Posted 3 hours ago
Ethan Allen Hotel

Find out more about Westport

Westport Vacation Homes information

Number of reviews
398
Accommodation
283 Vacation Homes
Lowest Price
￥24,201
Highest Price
￥345,200