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

Search Holiday Homes in Darien

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Darien holiday homes

An outdoor seating area with a round table, a chair, and a hanging light fixture.

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)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is £334
includes taxes & fees
2 Nov - 3 Nov
Gem by the water+ firepit and all fenced backyard
A living room with a sofa, armchair, ottoman, and coffee table.

2. 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 £375
includes taxes & fees
3 Nov - 4 Nov
Stamford Home | Family, Work and Plenty of Parking
A modern kitchen with white cabinets, a marble island, and black bar stools.

3. 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 £582
includes taxes & fees
18 Nov - 19 Nov
Spacious Retreat with Game Room and Fire Pit
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

4. 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 £263
includes taxes & fees
3 Nov - 4 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Open concept kitchen

5. 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.
The price is £1,343
includes taxes & fees
24 Nov - 25 Nov
5BR Beach House, Game Room + Huge Backyard
A modern living room with a white sofa, a glass coffee table, and a piano.

6. 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 £426
includes taxes & fees
2 Nov - 3 Nov
Spacious 3BR Townhome | Garage + Near Downtown
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.

7. 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, (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 £792
includes taxes & fees
1 Nov - 2 Nov
5BR Beach House, Water Views, Steps to Beach, Backyard
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

8. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.6 out of 10, Exceptional, (27 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
The price is £893
includes taxes & fees
6 Nov - 7 Nov
5BR Beach Home | Walk to Cove Beach + Private Yard
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

9. 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 £501
includes taxes & fees
9 Nov - 10 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

10. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is £427
includes taxes & fees
2 Nov - 3 Nov
Gilded Age Luxury Surrounded by Nature
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, (2 reviews)
"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 £1,795
includes taxes & fees
1 Nov - 2 Nov
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A modern kitchen with a marble island, bar stools, and a built-in oven.

12. 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 £310
includes taxes & fees
30 Nov - 1 Dec
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

13. 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 £410
includes taxes & fees
3 Nov - 4 Nov
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A swimming pool at night with blue lighting.

14. 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 £117
includes taxes & fees
5 Nov - 6 Nov
Business or Weekend escape
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

15. 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 £203
includes taxes & fees
3 Nov - 4 Nov
Centric property close to all the great things in the city
A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

16. 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, (88 reviews)
"Comfortable beds and close to good food"
United States
Stacey S.
The price is £483
includes taxes & fees
8 Nov - 9 Nov
Captain's Cottage - Cold Spring Harbor Water Views
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

17. Elite room stay

Elite room stay
Bridgeport
The price is £260
includes taxes & fees
31 Oct - 1 Nov
Elite room stay
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, (30 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 £647
includes taxes & fees
1 Nov - 2 Nov
Stay at Black Rock Harbor
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

19. 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 £460
includes taxes & fees
9 Nov - 10 Nov
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.

20. 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, (21 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 £587
includes taxes & fees
3 Nov - 4 Nov
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Darien Hotel Reviews

Ethan Allen Hotel

Ethan Allen Hotel

10/10 Excellent
"Clean staff is always pleasant parking is convenient"
Maksida 1-night trip
Posted 3 hours ago
Ethan Allen Hotel

Find out more about Darien

Darien Holiday Homes information

Number of reviews
387
Accommodation
205 Holiday Homes
Lowest Price
£117
Highest Price
£1,795