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 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 NZ$756
includes taxes & fees
28 Sept - 29 Sept
Gilded Age Luxury Surrounded by Nature
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

2. 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 NZ$459
includes taxes & fees
26 Sept - 27 Sept
Centric property close to all the great things in the city
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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is NZ$1,052
includes taxes & fees
30 Sept - 1 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

4. 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 NZ$1,002
includes taxes & fees
28 Sept - 29 Sept
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
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 NZ$588
includes taxes & fees
26 Sept - 27 Sept
Elite room stay
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

6. 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 NZ$1,217
includes taxes & fees
30 Sept - 1 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
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 NZ$269
includes taxes & fees
4 Oct - 5 Oct
Business or Weekend escape
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

8. 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.
The price is NZ$576
includes taxes & fees
30 Sept - 1 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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 NZ$1,502
includes taxes & fees
14 Oct - 15 Oct
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 NZ$1,310
includes taxes & fees
27 Sept - 28 Sept
4 Mi to Beach & Dtwn! Charming Fairfield Home
A campfire with a wooden table and benches by a lake.

11. 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 NZ$545
includes taxes & fees
5 Oct - 6 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A bedroom with two beds, a wooden dresser, and a mirror.

12. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is NZ$821
includes taxes & fees
26 Sept - 27 Sept
Cozy 1-bedroom house in welcoming Bridgeport
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

13. 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 NZ$1,667
includes taxes & fees
20 Oct - 21 Oct
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
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 NZ$1,032
includes taxes & fees
27 Sept - 28 Sept
Spacious Stamford Home | Family, Work, Parking
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

15. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is NZ$2,646
includes taxes & fees
27 Sept - 28 Sept
Beechmont - Perfect for Family Retreat!
A two-story house with a porch, stone steps, and a variety of plants.

16. 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 NZ$2,258
includes taxes & fees
6 Oct - 7 Oct
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

17. Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (85 reviews)
"A beautiful home and you cannot beat the views and location!"
United States
Daniel M.
The price is NZ$906
includes taxes & fees
28 Sept - 29 Sept
Captain's Cottage - Cold Spring Harbor Water Views
A living room with a staircase, a sofa, a coffee table, and a TV.

18. Loft •Pool • Gym • Free Parking • Near Yale

Loft •Pool • Gym • Free Parking • Near Yale
Orange
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. Host was accommodating and quick to respond when we encountered issues."
United States
Ali B.
The price is NZ$466
includes taxes & fees
27 Sept - 28 Sept
Loft •Pool • Gym • Free Parking • Near Yale
A modern living room with hardwood flooring, a leather sofa, a round coffee table, and a wooden side table. There is a dining area with a table and chairs visible in the background.

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

Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
Shelton
The price is NZ$839
includes taxes & fees
27 Sept - 28 Sept
Luxurious-Modern feel w/ custom features - AC, short walk to Shelton
A living room with two white sofas, a glass coffee table, a fireplace, and a flat-screen TV mounted above it.

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 NZ$1,315
includes taxes & fees
5 Oct - 6 Oct
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

Ethan Allen Hotel

Ethan Allen Hotel

8/10 Good
"It’s a decent hotel! Not too bad for a night stay."
Philip 1-night trip
Posted 2 hours ago
Ethan Allen Hotel

Find out more about Westport

Westport Holiday Homes information

Number of reviews
323
Accommodation
283 Holiday Homes
Lowest Price
NZ$269
Highest Price
NZ$2,646