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Browse Select Darien Vacation Homes

Charming 3-bedroom modern family retreat!

10.0 out of 10, Exceptional, (1)
"Spacious, clean and host was very responsive to any questions we had ! "
The price is CA $415
CA $630 total
includes taxes & fees
Sep 2 - Sep 3
Charming 3-bedroom modern family retreat!

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
"We stayed with family at this lovely home for my son’s graduation and Mother’s Day. The home is even nicer than the pictures- everything is top notch. It’s one block from a nice beach with lovely views from many of the rooms. We would love to come back and stay! "
Stareway to Heaven Su

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.8 out of 10, Exceptional, (6)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield

⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC

4.0 star property
10.0 out of 10, Exceptional, (7)
"This place was perfect for our family members - 7 adults. Everyone had their own bed and there were plenty of pillows and towels for all. It was quite clean and decorated nicely. The kitchen was well stocked with anything we might need and more. Thank you to the excellent hosts!"
⭐️❤️Historic Town ⭐️ Bridge View ⭐️ Walk Everywhere ⭐️ Quick Train to NYC

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (36)
"Short trip. great place to stay . Very cozy . Family loved it "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Business or Weekend escape

9.2 out of 10, Wonderful, (45)
"Very nice owner with great communication. "
The price is CA $118
CA $203 total
includes taxes & fees
Sep 14 - Sep 15
Business or Weekend escape

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (63)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Lovely little home in Stamford."
The price is CA $242
CA $493 total
includes taxes & fees
Sep 1 - Sep 2
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (33)
"House was very clean and maintained. We needed to check in a day later and the host was very accommodating. Overall a great place to stay! "
Cheerful 4 bedrooms residential house.

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (66)
"Great home to stay. Beautiful area to explore!"
The price is CA $491
CA $923 total
includes taxes & fees
Sep 8 - Sep 9
Captain's Cottage - Cold Spring Harbor Water Views

Charming New York Escape Near Central Park!

7.2 out of 10, Good, (15)
"Great area, good air conditioning equipment and tv's etc. The basement has the 2nd washroom, water didn't work except for the shower so hopefully that gets fixed soon. WiFi password on the modem was old so I had to contact to obtain the actual password, hopefully that also gets updated. Some of the towels had stains on them which is not a problem to me since I brought my own, but my brother was using it so that was a little disappointing too. Otherwise I'd say it was a great stay for the price...
Charming New York Escape Near Central Park!

Spacious 4-bedroom house in charming Rye with AC

The price is CA $277
CA $628 total
includes taxes & fees
Aug 25 - Aug 26
Spacious 4-bedroom house in charming Rye with AC

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is CA $226
CA $435 total
includes taxes & fees
Sep 16 - Sep 17
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

10.0 out of 10, Exceptional, (10)
"Super enjoyable."
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (3)
"Check in was super simple and easy. Kitchen area was so clean and neat. Overall stay was a wonderful experience. "
Soothing Carriage House with Hot Tub in charming Stratford

Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!

9.8 out of 10, Exceptional, (10)
"Very nice place close to the beach and nice restaurant. The host was very nice and did a very good banana cake."
Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (28)
"This property was perfect for our needs! Checking in and out was simple and easy. The house is spacious and backyard is gorgeous! "
Lakeside luxury: beautiful, relaxing 4 bedroom home

Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

2.0 star property
9.8 out of 10, Exceptional, (12)
"Clean and spacious apartment in a quiet neighborhood."
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

Family Friendly, Modern and Spacious 5-bedroom house in marvelous Westport, CT!

10.0 out of 10, Exceptional, (1)
"Excellent, high end, clean family home that deliveries a comfortable stay. A wonderful new build house, quite street, excellent communication from the owner and quality furnishings and fittings throughout the property. My daughters loved the playroom, their bedrooms and the trampoline! "
Family Friendly, Modern and Spacious 5-bedroom house in marvelous Westport, CT!
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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