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Compare 285 Vacation Homes in Old Greenwich with updated reviews, rates, and availability.

Lower Lvl Private 2BR/1BA Family/Pet Friendly
Exterior
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (114)
"Peaceful, lovely neighborhood. Easy access to country drives. Quick drive to Stamford station. Helpful host. "
Lower Lvl Private 2BR/1BA Family/Pet Friendly
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Living room
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
9.0 out of 10, Wonderful, (18)
"Great space. Clean sheets and towels. Wonderful shower. Great balcony I highly recommend!"
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
1-bedroom vacation home 12 minutes from Bronx Zoo
Room
1-bedroom vacation home 12 minutes from Bronx Zoo
9.8 out of 10, Exceptional, (22)
"We stayed for several days because the price was 1/4 the price of staying in the city. The apartment was clean and private. Parking was free and we ran in the neighborhood each morning. Everyone we met was very nice. "
1-bedroom vacation home 12 minutes from Bronx Zoo
Charming New York Escape Near Central Park!
Jericho Vacation Rental | 3BR | 2BA | 1,500 Sq Ft | Stairs Required for Access
Charming New York Escape Near Central Park!
7.2 out of 10, Good, (5)
"Got dropped off at the H-Mart from the airport and did my shopping and then walked over, as the host mentioned it was within walking distance and they were right! Super convenient. Well laid out, thoughtful instructions, everything was super easy. Ideal location for a couple of adults to stay to attend a convention. Also, there are workspaces in both of the bedrooms, which was a nice touch. "
Charming New York Escape Near Central Park!
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
Private kitchen
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
9.4 out of 10, Exceptional, (8)
"Great place for a group of friends to use as homebase for some shows at the Capitol Theater. "
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
Exterior
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
10.0 out of 10, Exceptional, (34)
"Our stay at Gersende's property was delightful. We had seven friends together for a wedding and this house and property served as a much appreciated comfortable and peaceful retreat. The pool was lovely, the kitchen was well-stocked and functional and the homes quirks and charm grew on us a little more each day. We walked to GrayBarns Mercantile every morning for coffee and it was a quick drive from the grocery as well as the PJ Glass House. Gersende was kind, easy to reach and incredibly...
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
Peaceful 5 Bed NY Villa - 30 min from NYC
Living area
Peaceful 5 Bed NY Villa - 30 min from NYC
9.0 out of 10, Wonderful, (6)
"Spacious and cozy home. Would love to come back in the summer to enjoy the yard. Perfect for families."
Peaceful 5 Bed NY Villa - 30 min from NYC
Stylish Beach Home near Stamford Downtown/Beach
Cozy backyard with fire pit and BBQ grill
Stylish Beach Home near Stamford Downtown/Beach
10.0 out of 10, Exceptional, (19)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
The price is AED 1,271
AED 2,956 total
includes taxes & fees
22 Nov - 23 Nov
Stylish Beach Home near Stamford Downtown/Beach
Romance Vacation Sweet Home
Living area
Romance Vacation Sweet Home
9.4 out of 10, Exceptional, (11)
"The house was immaculate and communication was outstanding! Will stay there every time we come to Long Island!"
Romance Vacation Sweet Home
Glen Cove Home: Walk to Boardwalk + Dining!
Glen Cove Vacation Rental | 3BR | 2BA | 1,500 Sq Ft | 2 Steps to Enter
Glen Cove Home: Walk to Boardwalk + Dining!
9.0 out of 10, Wonderful, (10)
"We had a good time staying at this and the adjoining property. "
Glen Cove Home: Walk to Boardwalk + Dining!
Family-Friendly, Near-NYC Norwalk Retreat
Cozy living room filled with art and entertainment
Family-Friendly, Near-NYC Norwalk Retreat
2.0 star property
10.0 out of 10, Exceptional, (2)
"Met all of our expectations, made a very enjoyable stay with 2 little ones. Host was accommodating and went above and beyond to support our needs. "
The price is AED 883
AED 2,166 total
includes taxes & fees
9 Dec - 10 Dec
Family-Friendly, Near-NYC Norwalk Retreat
Beautiful Hampton Long Island Family Getaway with Pool.
Property grounds
Beautiful Hampton Long Island Family Getaway with Pool.
7.6 out of 10, Good, (5)
"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 3,489
AED 5,978 total
includes taxes & fees
22 Nov - 23 Nov
Beautiful Hampton Long Island Family Getaway with Pool.
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
Private kitchen
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
2.0 star property
8.0 out of 10, Very Good, (2)
"The apartment is on the second floor on a dead end st. It is very clean and spacious with new appliances. Host are lovely couple. I only wish that the second bedroom had a full length mirror or any mirror. The master bedroom has 2 and the other had none. Had to keep going into the other room to use mirror. Had trouble using the TV, finally I had to mirror cast/share screen from my cell phone to the tv in order to watch anything. Overall it was a lovely and will go again. "
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
Captain's Cottage - Cold Spring Harbor Water Views
View Cold Spring Harbor in the Fall
Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (52)
"The captain cottage was exactly what Mom and I wanted! Beautiful views of the bay,super easy five minute walk to the main street of Cold Spring Harbor, adorable house with everything you need, and Kim was on top of it every time we neededhelp. Thank you so much for hosting us and cannot wait to be back!"
The price is AED 735
AED 1,554 total
includes taxes & fees
3 Dec - 4 Dec
Captain's Cottage - Cold Spring Harbor Water Views
Luxury 3Bed Private Apartment Near Manhattan
Living area
Luxury 3Bed Private Apartment Near Manhattan
9.0 out of 10, Wonderful, (10)
"everything was very good but street parking not sasy"
The price is AED 1,084
AED 1,822 total
includes taxes & fees
24 Nov - 25 Nov
Luxury 3Bed Private Apartment Near Manhattan
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Adorable Cottage with Water Views, Across the street from Prime & other eateries
9.8 out of 10, Exceptional, (60)
"We enjoyed our short stay at the cottage! The thoughtful amenities were appreciated (especially ALL your coffee needs except dairy, toiletries, filtered water ready in the fridge), and there were probably more we didn’t take advantage of…we were only there for 3 days and didn’t cook in the house but noticed the pantry was stocked with spices and cooking essentials. The beds and bedding were very comfortable. The outdoor area was lovely and well maintained but we didn’t use it much because of...
Adorable Cottage with Water Views, Across the street from Prime & other eateries
2 mini-bedrooms apartment with antique bathtub.
Private kitchen
2 mini-bedrooms apartment with antique bathtub.
10.0 out of 10, Exceptional, (18)
"Conveniently located to small downtown area & train into NYC. "
2 mini-bedrooms apartment with antique bathtub.
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Modern mid century guest house. Built in 1955 inside of old court
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
10.0 out of 10, Exceptional, (23)
"The property is absolutely stunning, very peaceful and Zen! Olga is fantastic very caring and attentive to detail. This was the perfect anniversary getaway and I can’t wait to go back."
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
LUXE 3BD/2BA 29 min>NYC w/Parking & deck
Living area
LUXE 3BD/2BA 29 min>NYC w/Parking & deck
10.0 out of 10, Exceptional, (13)
"The listing is accurate, perfect location to walk to train, restaurants and so much more! We were delighted to stay there and we look forward to staying in the future!! Thanks Dan"
LUXE 3BD/2BA 29 min>NYC w/Parking & deck
A 1BR close to White Plains Train Station
Living area
A 1BR close to White Plains Train Station
9.8 out of 10, Exceptional, (8)
"Very nice place. Great furnishings, bed, shower,parking, communications,quite."
A 1BR close to White Plains Train Station
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
Property amenity
Stamford Suites
2.5 star property
6.8 out of 10, (766)
"All is well"
The price is AED 528
AED 591 total
includes taxes & fees
27 Nov - 28 Nov
Stamford Suites
DUNE Fairfield Beach
Room
DUNE Fairfield Beach
3.0 star property
8.8 out of 10, Excellent, (42)
"The property is generally old, but it was a nice renovation. Of the room. "
The price is AED 1,235
AED 1,580 total
includes taxes & fees
30 Nov - 1 Dec
DUNE Fairfield Beach
Waterfront Retreat Center for Health & Wellness
Exterior
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (54)
"This is my second state at the New Dawn house and it was just as wonderful as last year. I can't think of a better place for a large gathering in the Bronx area. "
Waterfront Retreat Center for Health & Wellness
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.