Two wooden benches facing a calm body of water under a clear sky.

Holiday Homes in Darien

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Darien holiday homes

A bedroom with a bed, bedside tables, a mirror, a wardrobe, and a painting on the wall.

1. 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, (21 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is NZ$813
includes taxes & fees
19 Oct - 20 Oct
Gem by the water+ firepit and all fenced backyard
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

2. 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, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is NZ$647
includes taxes & fees
15 Nov - 16 Nov
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.

3. 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$1,061
includes taxes & fees
27 Oct - 28 Oct
Spacious Stamford Home | Family, Work, Parking
A modern kitchen with white cabinets, a marble island, and black bar stools.

4. 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$1,310
includes taxes & fees
5 Nov - 6 Nov
Spacious Retreat with Game Room and Fire Pit
A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

5. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is NZ$996
includes taxes & fees
19 Oct - 20 Oct
Gilded Age Luxury Surrounded by Nature
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.

6. 5BR Beach House, Water Views, Steps to Beach, Backyard

5BR Beach House, Water Views, Steps to Beach, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 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 NZ$1,764
includes taxes & fees
20 Oct - 21 Oct
5BR Beach House, Water Views, Steps to Beach, Backyard
A modern living room with a white sofa, a glass coffee table, and a piano.

7. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.2 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 NZ$1,227
includes taxes & fees
27 Oct - 28 Oct
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

8. 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$1,159
includes taxes & fees
9 Nov - 10 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Open concept kitchen

9. 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)
"Very spacious and nicely decorated"
United States
Linda M.
5BR Beach House, Game Room + Huge Backyard
A swimming pool at night with blue lighting.

10. 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 NZ$269
includes taxes & fees
18 Oct - 19 Oct
Business or Weekend escape
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

11. 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$415
includes taxes & fees
18 Oct - 19 Oct
Centric property close to all the great things in the city
A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

12. 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, (87 reviews)
"Comfortable beds and close to good food"
United States
Stacey S.
The price is NZ$909
includes taxes & fees
27 Oct - 28 Oct
Captain's Cottage - Cold Spring Harbor Water Views
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

13. 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 NZ$4,223
includes taxes & fees
19 Oct - 20 Oct
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

14. Elite room stay

Elite room stay
Bridgeport
The price is NZ$600
includes taxes & fees
18 Oct - 19 Oct
Elite room stay
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

15. 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 NZ$1,012
includes taxes & fees
21 Oct - 22 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.

16. 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$1,065
includes taxes & fees
16 Nov - 17 Nov
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A modern kitchen with a marble island, bar stools, and a built-in oven.

17. Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is NZ$798
includes taxes & fees
9 Nov - 10 Nov
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A white room with a round table, two benches, and a window with a view of houses.

18. Stay at Black Rock Harbor

Stay at Black Rock Harbor
Black Rock Historic District
10.0 out of 10, Exceptional, (29 reviews)
"This house was perfect for our family. Will definitely use again when we're visiting family in the area."
United States
Laura L.
The price is NZ$1,630
includes taxes & fees
1 Nov - 2 Nov
Stay at Black Rock Harbor
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

19. 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$1,374
includes taxes & fees
20 Oct - 21 Oct
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
An outdoor patio with a fire pit, green chairs, and a table.

20. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
10.0 out of 10, Exceptional, (12 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is NZ$605
includes taxes & fees
27 Oct - 28 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
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 Darien Hotel Reviews

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"All around great safe place to stay"
Susan 6-night trip
Posted 10 hours ago
Norwalk Inn & Conference Center

Find out more about Darien

Darien Holiday Homes information

Number of reviews
407
Accommodation
235 Holiday Homes
Lowest Price
NZ$269
Highest Price
NZ$4,223