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

Holiday Homes in Darien

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Our top choices for Darien holiday homes

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, Exceptional, (18 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is NZ$631
includes taxes & fees
15 Sept - 16 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

2. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is NZ$723
includes taxes & fees
28 Sept - 29 Sept
Gilded Age Luxury Surrounded by Nature

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, 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$1,147
includes taxes & fees
3 Sept - 4 Sept
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

4. 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$963
includes taxes & fees
3 Sept - 4 Sept
Spacious Stamford Home | Family, Work, Parking

5. 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)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
The price is NZ$682
includes taxes & fees
20 Sept - 21 Sept
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

6. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, Exceptional, (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 NZ$1,333
includes taxes & fees
24 Sept - 25 Sept
Spacious Retreat with Game Room and Fire Pit

7. 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 NZ$1,532
includes taxes & fees
3 Sept - 4 Sept
5BR Beach House, Game Room + Huge Backyard

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, Exceptional, (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 NZ$1,215
includes taxes & fees
3 Sept - 4 Sept
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

9. 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 NZ$1,640
includes taxes & fees
22 Sept - 23 Sept
5BR Beach House, Water Views, Game Room, Backyard

10. 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, (16 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is NZ$449
includes taxes & fees
3 Sept - 4 Sept
Centric property close to all the great things in the city

11. 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 NZ$258
includes taxes & fees
29 Sept - 30 Sept
Business or Weekend escape

12. The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace

The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace
Cove - East Side - Shippan
9.0 out of 10, Wonderful, (10 reviews)
"Beautiful place, very clean. Great Host!"
United States
Alejandro A.
The price is NZ$1,799
includes taxes & fees
7 Sept - 8 Sept
The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace

13. Elite room stay

Elite room stay
Bridgeport
The price is NZ$568
includes taxes & fees
3 Sept - 4 Sept
Elite room stay

14. 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, (84 reviews)
"A beautiful home and you cannot beat the views and location!"
United States
Daniel M.
The price is NZ$877
includes taxes & fees
9 Sept - 10 Sept
Captain's Cottage - Cold Spring Harbor Water Views

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, (39 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is NZ$1,000
includes taxes & fees
21 Sept - 22 Sept
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

16. 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$765
includes taxes & fees
8 Sept - 9 Sept
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

17. 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, (18 reviews)
"Convenient to everything. Lovely place to stay."
United States
Tami S.
The price is NZ$1,046
includes taxes & fees
30 Sept - 1 Oct
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

18. Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability

Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability
New Canaan
10.0 out of 10, Exceptional, (43 reviews)
"Unique home with beautiful grounds and classically designed interior. Perfect for relaxing and enjoying with family/friends."
United States
David
The price is NZ$3,906
includes taxes & fees
7 Sept - 8 Sept
Private French Country Estate-New Canaan CT-Pool-Film Set- Aug&Sept availability

19. 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, Exceptional, (9 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is NZ$584
includes taxes & fees
7 Sept - 8 Sept
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

20. 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 NZ$1,254
includes taxes & fees
7 Sept - 8 Sept
4 Mi to Beach & Dtwn! Charming Fairfield Home
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

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Darien Holiday Homes information

Number of reviews
Accommodation
270 Holiday Homes
Lowest Price
NZ$2,077
Highest Price
NZ$2,532