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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Darien holiday homes

A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

1. 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, 19, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is €332
includes taxes & fees
20 Sept - 21 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A bedroom with two beds, a nightstand with a lamp, a framed picture on the wall, and a window with curtains.

2. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is €379
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.

3. 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, 15, (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 €592
includes taxes & fees
16 Sept - 17 Sept
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A campfire with a wooden table and benches by a 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, 42, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is €299
includes taxes & fees
4 Oct - 5 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern kitchen with white cabinets, a marble island, and black bar stools.

5. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, 2, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
The price is €663
includes taxes & fees
16 Sept - 17 Sept
Spacious Retreat with Game Room and Fire Pit
A living room with a sofa set, a coffee table, and a television on a stand.

6. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, 9, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is €493
includes taxes & fees
15 Sept - 16 Sept
Spacious Stamford Home | Family, Work, Parking
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, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, 31, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is €757
includes taxes & fees
21 Sept - 22 Sept
5BR Beach House, Water Views, Game Room, Backyard
A kitchen counter with a bottle of olive oil, a utensil holder with 'What's Cookin?' text, a knife block, and a kettle.

8. 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, 8, (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 €719
includes taxes & fees
22 Sept - 23 Sept
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

9. 5BR Beach House, Game Room + Huge Backyard

5BR Beach House, Game Room + Huge Backyard
Cove - East Side - Shippan
10.0 out of 10, 26, (26 reviews)
"Great stay!"
United States
Kyra S.
The price is €986
includes taxes & fees
16 Sept - 17 Sept
5BR Beach House, Game Room + Huge Backyard
A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

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

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, 84, (84 reviews)
"A beautiful home and you cannot beat the views and location!"
United States
Daniel M.
The price is €399
includes taxes & fees
21 Sept - 22 Sept
Captain's Cottage - Cold Spring Harbor Water Views
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, (17 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is €233
includes taxes & fees
15 Sept - 16 Sept
Centric property close to all the great things in the city
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

12. 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, 18, (18 reviews)
"Place was very clean . Communication between owner and us was excellent."
United States
gail s.
The price is €499
includes taxes & fees
16 Sept - 17 Sept
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A swimming pool at night with blue lighting.

13. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, 59, (59 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is €135
includes taxes & fees
12 Oct - 13 Oct
Business or Weekend escape
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 €295
includes taxes & fees
15 Sept - 16 Sept
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, 39, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is €558
includes taxes & fees
5 Oct - 6 Oct
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern kitchen with a marble island, bar stools, and a built-in oven.

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

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, 5, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is €400
includes taxes & fees
20 Sept - 21 Sept
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
An outdoor patio with a fire pit, green chairs, and a table.

17. 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
9.8 out of 10, 10, (10 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is €313
includes taxes & fees
7 Oct - 8 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A wooden deck with chairs and a kayak, leading to a beach with a view of the ocean.

18. Shore to Shore Coastal Retreat at Asharoken

Shore to Shore Coastal Retreat at Asharoken
Northport
The price is €976
includes taxes & fees
21 Sept - 22 Sept
Shore to Shore Coastal Retreat at Asharoken
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

19. Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, 1, (1 review)
"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...
United States
James D.
The price is €473
includes taxes & fees
15 Sept - 16 Sept
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

20. NYC-Area Escape Near River, Trails & MTA!

NYC-Area Escape Near River, Trails & MTA!
Ossining
8.2 out of 10, 19, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
The price is €717
includes taxes & fees
15 Sept - 16 Sept
NYC-Area Escape Near River, Trails & MTA!
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

Amsterdam Hotel

Amsterdam Hotel

8/10 Good
"Vending machine not much , lady at front desk nice . Breakfast was ok nothing to Write home about . Parking turns suck . Room nice ."
Gene 3-night trip
Posted 1 hour ago
Amsterdam Hotel

Find out more about Darien

Darien Holiday Homes information

Number of reviews
353
Accommodation
270 Holiday Homes
Lowest Price
€135
Highest Price
€986