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Holiday Homes in Westport

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Our top choices for Westport holiday homes

1. 3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ

3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
Cranbury
8.8 out of 10, Excellent, (8 reviews)
"Great spot for our family. "
United States
Kevin I.
The price is €532
includes taxes & fees
19 Nov - 20 Nov
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ

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, (16 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 €610
includes taxes & fees
15 Nov - 16 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

3. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is €366
includes taxes & fees
18 Nov - 19 Nov
Gilded Age Luxury Surrounded by Nature

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, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is €488
includes taxes & fees
12 Nov - 13 Nov
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

5. 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)
"Beautiful home, clean and exactly as described.We loved our stay and plan on returning.The host was wonderful to work with.An overall excellent experience."
United States
Tara C.
The price is €488
includes taxes & fees
12 Nov - 13 Nov
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

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
6.8 out of 10, (18 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is €231
includes taxes & fees
22 Nov - 23 Nov
Centric property close to all the great things in the city

7. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is €132
includes taxes & fees
12 Nov - 13 Nov
Business or Weekend escape

8. Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is €1,109
includes taxes & fees
24 Nov - 25 Nov
Stareway to Heaven in Fairfield

9. Elite room stay

Elite room stay
Bridgeport
The price is €296
includes taxes & fees
13 Nov - 14 Nov
Elite room stay

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
9.6 out of 10, Exceptional, (22 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 €691
includes taxes & fees
15 Nov - 16 Nov
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

11. 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 €701
includes taxes & fees
18 Nov - 19 Nov
Spacious Retreat with Game Room and Fire Pit

12. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
6.0 out of 10, (2 reviews)
"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 €796
includes taxes & fees
12 Nov - 13 Nov
4 Mi to Beach & Dtwn! Charming Fairfield Home

13. Stamford Home | Family, Work and Plenty of Parking

Stamford Home | Family, Work and Plenty of 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 €411
includes taxes & fees
16 Nov - 17 Nov
Stamford Home | Family, Work and Plenty of Parking

14. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (22 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is €391
includes taxes & fees
16 Nov - 17 Nov
Gem by the water+ firepit and all fenced backyard

15. Renovated Beachside Retreat

Renovated Beachside Retreat
Milford
10.0 out of 10, Exceptional, (1 review)
"Terrific place to stay in Milford. Quaint & quiet neighborhood, close to beach and beautiful park near by to walk at (Walnut Beach Park). House was very well kept and stocked with everything you would need. Host communication was thorough and prompt. Would absolutely stay here again."
United States
Michelle D.
Renovated Beachside Retreat

16. 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, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is €293
includes taxes & fees
12 Nov - 13 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

17. 5BR Beach House | Water Views + Sauna + Game Room

5BR Beach House | Water Views + Sauna + Game Room
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (32 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 €789
includes taxes & fees
15 Nov - 16 Nov
5BR Beach House | Water Views + Sauna + Game Room

18. 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 €1,102
includes taxes & fees
18 Nov - 19 Nov
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

19. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is €953
includes taxes & fees
12 Nov - 13 Nov
Beechmont - Perfect for Family Retreat!

20. Spacious 3BR Townhome | Garage + Near Downtown

Spacious 3BR Townhome | Garage + Near Downtown
West Side
9.2 out of 10, Wonderful, (9 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 €467
includes taxes & fees
15 Nov - 16 Nov
Spacious 3BR Townhome | Garage + Near Downtown
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

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Westport Holiday Homes information

Number of reviews
284
Accommodation
274 Holiday Homes
Lowest Price
€132
Highest Price
€1,109