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

Darien Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Darien vacation 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, Exceptional, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is CA $223
CA $465 total
includes taxes & fees
Sep 30 - Oct 1
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

2. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 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 CA $337
CA $937 total
includes taxes & fees
Sep 30 - Oct 1
5BR Beach Home | Walk to Cove Beach + Private Yard
A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

3. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is CA $281
CA $543 total
includes taxes & fees
Oct 12 - Oct 13
Gilded Age Luxury Surrounded by Nature
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, Exceptional, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is CA $230
CA $444 total
includes taxes & fees
Oct 7 - Oct 8
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.

5. 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 CA $377
CA $768 total
includes taxes & fees
Sep 30 - Oct 1
Spacious Stamford Home | Family, Work, Parking
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

6. 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 CA $421
CA $989 total
includes taxes & fees
Oct 28 - Oct 29
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A modern kitchen with white cabinets, a marble island, and black bar stools.

7. 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 CA $574
CA $1,199 total
includes taxes & fees
Oct 14 - Oct 15
Spacious Retreat with Game Room and Fire Pit
A modern living room with a white sofa, a glass coffee table, and a piano.

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 CA $473
CA $924 total
includes taxes & fees
Oct 27 - Oct 28
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
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.

9. 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)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is CA $668
CA $1,328 total
includes taxes & fees
Oct 14 - Oct 15
5BR Beach House, Water Views, Steps to Beach, Backyard
Open concept kitchen

10. 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 CA $527
CA $1,261 total
includes taxes & fees
Oct 6 - Oct 7
5BR Beach House, Game Room + Huge Backyard
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

11. 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, (40 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is CA $274
CA $784 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

12. 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 CA $223
CA $378 total
includes taxes & fees
Oct 4 - Oct 5
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.

13. 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 CA $290
CA $803 total
includes taxes & fees
Sep 30 - Oct 1
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
An outdoor patio with a fire pit, green chairs, and a table.

14. 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, (11 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is CA $208
CA $503 total
includes taxes & fees
Oct 20 - Oct 21
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

15. 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, (86 reviews)
"A beautiful home and you cannot beat the views and location!"
United States
Daniel M.
The price is CA $326
CA $719 total
includes taxes & fees
Oct 1 - Oct 2
Captain's Cottage - Cold Spring Harbor Water Views
A swimming pool at night with blue lighting.

16. 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 CA $128
CA $216 total
includes taxes & fees
Oct 4 - Oct 5
Business or Weekend escape
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 CA $293
CA $485 total
includes taxes & fees
Sep 30 - Oct 1
Elite room stay
A modern kitchen with a marble island, bar stools, and a built-in oven.

18. 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 CA $354
CA $645 total
includes taxes & fees
Sep 30 - Oct 1
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

19. 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 CA $2,835
CA $4,351 total
includes taxes & fees
Oct 7 - Oct 8
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A room with two beds, white curtains, a ceiling light, and a window with a view.

20. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
2.0 out of 10, (1 review)
"This guy is a scammer, an hour before my checkin they finally sent me the "location" and claimed they needed more time to clean the property. Then at 5 pm and hour after they claimed their was a gas leak and I couldn't stay there. Only thing is the address they sent me wasn't real and I am convinced this listing is fake in and used to trick people into staying at their actual property in yonkers. DO NOT RENT FROM THEM!"
United States
Ethan G.
The price is CA $383
CA $775 total
includes taxes & fees
Sep 30 - Oct 1
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
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

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

10/10 Excellent
"Everything was wonderful. I would definitely book again!"
Kareem 2-night trip
Posted 1 hour ago
Baymont by Wyndham White Plains - Elmsford

Find out more about Darien

Darien Vacation Homes information

Number of reviews
367
Accommodation
253 Vacation Homes
Lowest Price
CA $216
Highest Price
CA $4,351

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