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 AU$600
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 AU$998
includes taxes & fees
29 Sept - 30 Sept
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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is AU$836
includes taxes & fees
27 Sept - 28 Sept
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 AU$811
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 AU$484
includes taxes & fees
27 Sept - 28 Sept
Elite room stay
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

6. 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 AU$381
includes taxes & fees
4 Oct - 5 Oct
Centric property close to all the great things in the city
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 AU$220
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 AU$470
includes taxes & fees
30 Sept - 1 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

9. 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 AU$1,075
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.

10. 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 AU$443
includes taxes & fees
5 Oct - 6 Oct
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.

11. 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 AU$808
includes taxes & fees
27 Sept - 28 Sept
Spacious Stamford Home | Family, Work, Parking
A modern kitchen with white cabinets, a marble island, and black bar stools.

12. 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 AU$1,243
includes taxes & fees
14 Oct - 15 Oct
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.

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 AU$1,333
includes taxes & fees
20 Oct - 21 Oct
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A bedroom with two beds, a wooden dresser, and a mirror.

14. Cozy 1-bedroom house in welcoming Bridgeport

Cozy 1-bedroom house in welcoming Bridgeport
Bridgeport
The price is AU$668
includes taxes & fees
27 Sept - 28 Sept
Cozy 1-bedroom house in welcoming Bridgeport
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 AU$1,762
includes taxes & fees
28 Sept - 29 Sept
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

16. 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)
"Great stay!"
United States
Kyra S.
The price is AU$1,310
includes taxes & fees
28 Sept - 29 Sept
5BR Beach House, Game Room + Huge Backyard
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

17. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is AU$1,015
includes taxes & fees
27 Sept - 28 Sept
Renovated Retreat with Heated Pool
A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

18. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is AU$2,133
includes taxes & fees
27 Sept - 28 Sept
Beechmont - Perfect for Family Retreat!
A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

19. 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 AU$717
includes taxes & fees
28 Sept - 29 Sept
Captain's Cottage - Cold Spring Harbor Water Views
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 AU$1,336
includes taxes & fees
14 Oct - 15 Oct
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

Amsterdam Hotel

Amsterdam Hotel

8/10 Good
"Great value for the area. Room decor is dated but in good condition. Very nice microwave, refrigerator and coffee maker area. Very large rooms."
Michael P 1-night trip
Posted 12 hours ago
Amsterdam Hotel

Find out more about Westport

Westport Holiday Homes information

Number of reviews
355
Accommodation
279 Holiday Homes
Lowest Price
AU$220
Highest Price
AU$2,133