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Compare 373 Vacation Homes in Old Greenwich with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (7)
"House is even cooler than the pictures give it credit for. Beautiful and funky. We really enjoyed our stay!!"
Historic Connecticut Home w/ Grill & Spacious Yard

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (58)
"Everything was awesome! Would definitely stay here again! "
The price is SAR 1,050
SAR 2,143 total
includes taxes & fees
12 May - 13 May
Captain's Cottage - Cold Spring Harbor Water Views

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (28)
"Its was perfect, quiet and spacious great little get away."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

9.6 out of 10, Exceptional, (11)
"Location was great! Having a car with off street parking, walk to station and well lit. Very clean, hot hot water (which I loved!) and plenty in the kitchen! Thank you!"
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

Luxury 3Bed Private Apartment Near Manhattan

9.2 out of 10, Wonderful, (12)
"Host was very accommodating and easy to communicate with!"
The price is SAR 1,219
SAR 2,295 total
includes taxes & fees
29 Apr - 30 Apr
Luxury 3Bed Private Apartment Near Manhattan

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"Dierdre's home was a perfect spot for our family Thanksgiving. Well located, well stocked, and very well cared for!"
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

Charming 3-bedroom house in Bronx with AC, WiFi

10.0 out of 10, Exceptional, (1)
"Mrs Helen was awesome. Loved her hospitality and she’s only next-door if you need her for anything."
Charming 3-bedroom house in Bronx with AC, WiFi

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"We were a family of 4 adults and 2 toddlers staying over Thanksgiving. We really didn’t need all the space but we certainly enjoyed it. There’s a huge well stocked kitchen, kids’ play areas on both the main floor and basement, and the property is massive and gorgeous. Great stay!"
Over Sized Colonial on Private Road.

Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

9.4 out of 10, Exceptional, (10)
"Perfect residential home to stay at"
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"We had a great time and it was a very spacious and clean location "
The price is SAR 1,759
SAR 3,454 total
includes taxes & fees
28 Apr - 29 Apr
New Beach Home near Stamford Downtown/Shippan

Charming 2-bedroom house with AC, WiFi in marvelous Nyack

2.0 star property
Charming 2-bedroom house with AC, WiFi in marvelous Nyack

Glen Cove Home: Walk to Boardwalk + Dining!

9.0 out of 10, Wonderful, (14)
"We enjoyed staying here for a long weekend while touring maritime colleges in the area. This nice quiet neighborhood was restful at the end of each day and convenient to everywhere we needed to be. The nearby brewery on the harbor was a great spot for lunch."
Glen Cove Home: Walk to Boardwalk + Dining!

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"Had a great time! My favorite part was sitting on the back deck w coffee in the morning. There were so many birds and the tall hedges that protected the privacy was so charming. The host was so nice and left out fruit and snacks. Loved staying there!"
Westport Gem - walk to shops, dining, town center, pet-friendly

Spacious Gorgeous Getaway perfect for family reunion or business

9.8 out of 10, Exceptional, (6)
"House was perfect for the group. We had everything we needed and plenty of room for us. Owner was great with communications before and during our stay"
Spacious Gorgeous Getaway perfect for family reunion or business

Cozy and beautiful house

10.0 out of 10, Exceptional, (21)
"Property owner was great at communicating and the house was perfect!"
Cozy and beautiful house

Charming Mamaroneck Home ~ 22 Mi to Manhattan

7.8 out of 10, Good, (12)
"Clean and easy check in--Great Location!"
Charming Mamaroneck Home ~ 22 Mi to Manhattan

Ossining Vacation Rental Near River, Trails & MTA!

8.4 out of 10, Very Good, (7)
"This was our Christmas gathering place for family from 4 states. Beautiful home and location. "
Ossining Vacation Rental Near River, Trails & MTA!

Breathtaking Waterfront house

9.4 out of 10, Exceptional, (3)
"Fun property, kitchen needs a little organizing, And instructions for tv and remotes would be helpful"
Breathtaking Waterfront house

Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

10.0 out of 10, Exceptional, (12)
"Clean, cozy and would stay again."
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.
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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Other property types in Old Greenwich

Stamford Suites

3.0 star property
5.8 out of 10, (28)
"Convenience. Full kitchen and spacious rooms"
The price is SAR 705
SAR 811 total
includes taxes & fees
27 Apr - 28 Apr
Stamford Suites

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (52)
"Absolutely perfect location for visiting Fairfield University! Everything about it exceeded our expectations."
The price is SAR 1,659
SAR 2,114 total
includes taxes & fees
2 May - 3 May
DUNE Fairfield Beach

Global Luxury Suites White Plains

3.5 star property
6.6 out of 10, (30)
"Nice view from the apartment and great for business trip. "
Global Luxury Suites White Plains
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.