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Vacation Homes in Old Greenwich

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (65)
"Great home to stay. Beautiful area to explore!"
The price is AED 1,175
AED 2,287 total
includes taxes & fees
10 Aug - 11 Aug
Captain's Cottage - Cold Spring Harbor Water Views

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

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 AED 547
AED 1,077 total
includes taxes & fees
7 Aug - 8 Aug
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Stylish Stay in City’s Best Spot- The Perfect Stay

3.0 out of 10, (2)
"I arrived in New York on 6-22-25 I requested the check in information in which the host refused to give. She stated the cleaner hadn't showed up to clean the property so she gave me another address. Well this place had multiple stairs and was located on the 2nd floor which couldn't accommodate the group I was with. When I informed the host she gave me another address which was smaller with one bathroom. Smaller than the original one booked. After explaining that this wouldn't work the host...
Stylish Stay in City’s Best Spot- The Perfect Stay

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Secluded Luxury Home – Peaceful, Comfortable, and Fully Private.

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is AED 1,308
AED 2,566 total
includes taxes & fees
3 Sep - 4 Sep
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Quaint duplex with private yard. Walk to beach, dining, & shopping!

10.0 out of 10, Exceptional, (44)
"Needed a place to stay with our dog while visiting our granddaughters in a nearby town."
Quaint duplex with private yard. Walk to beach, dining, & shopping!

Spacious 4-bedroom house in charming Rye with AC

The price is AED 735
AED 1,668 total
includes taxes & fees
7 Aug - 8 Aug
Spacious 4-bedroom house in charming Rye with AC

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

Luxury NY Home 3BR with Easy Parking

3.0 star property
3.0 out of 10, (4)
"I was fooled by the pictures. Upon check-in, they require to zelle cleaing fee. When I finally got inside, I found absolutely nothing lux about this property, no comfort and hospitality. The broken floor welcome me, all 4 beds are broken, only 2 TVs, moldy restroom, zero confort. They left 4 towels for 6 people for 6 nights. I had to request more towels. I had to scoop water fromthe shower to flush in the toilet because water would not drain. Half roll toilet paper was left. If you take...
Luxury NY Home 3BR with Easy Parking

St Julian's Place - Large updated Apt @ 40 Min NYC

10.0 out of 10, Exceptional, (35)
"This is the 3rd time we've stayed here. The apartment looks great and is convenient for us to visit family. We always enjoy staying here."
St Julian's Place - Large updated Apt @ 40 Min NYC

Main Street Westport, walk to shops, dining, downtown

9.0 out of 10, Wonderful, (2)
"Beautiful home, great location, communicative hosts…A"
Main Street Westport, walk to shops, dining, downtown

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

2.0 star property
9.8 out of 10, Exceptional, (12)
"Great location, quite dead end. Excellent value, we had a very comfortable stay.Walking distance to the station for Metro North into NYC. Great deli just around the corner. Responsive hosts, will gladly use again!! "
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

Lovely Basement with 2 Bedrooms and Kitchen

10.0 out of 10, Exceptional, (16)
"We enjoyed our stay so much we’ve already booked a second stay!"
Lovely Basement with 2 Bedrooms and Kitchen

La Casita Bonita near NYC

5.0 out of 10, (2)
"Convenient location to upstate snd downtown NYC. All the rooms were good size. Appreciate the welcoming outside space both out front and in the back area. Plan to come back later this year."
La Casita Bonita near NYC

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
The price is AED 2,200
AED 2,825 total
includes taxes & fees
7 Aug - 8 Aug
3BR Prime Luxury near NYC w Arcade Room

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

The price is AED 478
AED 734 total
includes taxes & fees
2 Sep - 3 Sep
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 3-bedrooms in a private house w/AC and WiFi 30min drive to Midtown NYC

8.0 out of 10, Very Good, (2)
"Good location and good host"
Charming 3-bedrooms in a private house w/AC and WiFi 30min drive to Midtown NYC

Charming Long Island Family Getaway with Pool. An hour from Hamptons

7.6 out of 10, Good, (7)
"Had a great time here. The house was clean and well maintained. The host communicated with us often and overall it was a great stay!"
The price is AED 2,200
AED 4,788 total
includes taxes & fees
6 Sep - 7 Sep
Charming Long Island Family Getaway with Pool. An hour from Hamptons
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 Old Greenwich Hotel Reviews