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

Holiday Homes in Westport

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Westport holiday homes

A bedroom with two beds, a nightstand with a lamp, a framed picture on the wall, and a window with curtains.

1. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is €372
includes taxes & fees
28 Sept - 29 Sept
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 €651
includes taxes & fees
19 Oct - 20 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

3. 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 €666
includes taxes & fees
24 Sept - 25 Sept
4 Mi to Beach & Dtwn! Charming Fairfield Home
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 €236
includes taxes & fees
24 Sept - 25 Sept
Centric property close to all the great things in the city
A modern kitchen with white cabinets, a marble island, and black bar stools.

5. 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 €680
includes taxes & fees
24 Sept - 25 Sept
Spacious Retreat with Game Room and Fire Pit
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 €299
includes taxes & fees
24 Sept - 25 Sept
Elite room stay
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

7. 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 €512
includes taxes & fees
21 Oct - 22 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

8. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is €1,307
includes taxes & fees
24 Sept - 25 Sept
Beechmont - Perfect for Family Retreat!
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

9. 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 €584
includes taxes & fees
21 Oct - 22 Oct
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.

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 €857
includes taxes & fees
20 Oct - 21 Oct
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

11. Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
Greenwich
10.0 out of 10, Exceptional, (1 review)
"Great location on the lake which the kids loved. The hosts were very friendly and easy to communicate with. The addition of the outdoor grill was a big plus and we enjoyed many afternoons out on the deck. We would stay again."
United States
Nathan R.
The price is €2,528
includes taxes & fees
27 Sept - 28 Sept
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A two-story house with a porch, stone steps, and a variety of plants.

12. 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 €1,085
includes taxes & fees
20 Oct - 21 Oct
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A bedroom with two beds, a wooden dresser, and a mirror.

13. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is €426
includes taxes & fees
24 Sept - 25 Sept
Cozy 1-bedroom house in welcoming Bridgeport
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

14. 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, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A swimming pool at night with blue lighting.

15. 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 €137
includes taxes & fees
5 Oct - 6 Oct
Business or Weekend escape
A living room with a sofa set, a coffee table, and a television on a stand.

16. 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 €554
includes taxes & fees
6 Oct - 7 Oct
Spacious Stamford Home | Family, Work, Parking
A kitchen counter with a bottle of olive oil, a utensil holder with 'What's Cookin?' text, a knife block, and a kettle.

17. 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.
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A wooden deck with chairs and a kayak, leading to a beach with a view of the ocean.

18. Shore to Shore Coastal Retreat at Asharoken

Shore to Shore Coastal Retreat at Asharoken
Northport
10.0 out of 10, Exceptional, (1 review)
"We had a great time at this Vrbo. The house is spacious and the backyard absolutely beautiful. We brought two babies under 2 and it was a perfect spot. The private beach is just steps away and lovely for low-key beach days. The fridge was not working properly, and Joe let us know ahead of time and provided us with a mini fridge that worked, which made everything easy. He also ordered us more paper towels and dish soap while we were there which was super helpful and accomodating. Would absolutely...
United States
Rachel W.
The price is €990
includes taxes & fees
28 Sept - 29 Sept
Shore to Shore Coastal Retreat at Asharoken
A campfire with a wooden table and benches by a lake.

19. 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)
"Nice stay"
United States
Christopher J.
The price is €271
includes taxes & fees
5 Oct - 6 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern kitchen with a marble island, bar stools, and a dining area with a table and chairs.

20. Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!

Luxe, designer renovation; walk to Tyde wedding venue, shops & beach!
Milford
9.8 out of 10, Exceptional, (9 reviews)
"Very comfortable modern home, clean, great backyard, pet friendly Host was so accommodating and responsive, personal note at check-in "
United States
Traci F.
The price is €404
includes taxes & fees
24 Sept - 25 Sept
Luxe, designer renovation; walk to Tyde wedding venue, shops & 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.
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Top Westport Hotel Reviews

Comfort Inn & Suites Danbury-Bethel

Comfort Inn & Suites Danbury-Bethel

10/10 Excellent
"Always a good stay here. Great breakfast"
Jim 2-night trip
Posted 1 hour ago
Comfort Inn & Suites Danbury-Bethel

Find out more about Westport

Westport Holiday Homes information

Number of reviews
246
Accommodation
278 Holiday Homes
Lowest Price
€137
Highest Price
€2,528