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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Old Greenwich vacation homes

An outdoor seating area with a round table, a chair, and a hanging light fixture.

1. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (21 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is AED 824
AED 1,633 total
includes taxes & fees
9 Nov - 10 Nov
Gem by the water+ firepit and all fenced backyard
A room with large windows overlooking a lake and greenery.

2. 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, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is AED 612
AED 1,203 total
includes taxes & fees
7 Nov - 8 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern living room with a white sofa, a glass coffee table, and a piano.

3. Spacious 3BR Townhome | Garage + Near Downtown

Spacious 3BR Townhome | Garage + Near Downtown
West Side
9.2 out of 10, Wonderful, (9 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 AED 1,050
AED 2,054 total
includes taxes & fees
11 Nov - 12 Nov
Spacious 3BR Townhome | Garage + Near Downtown
Open concept kitchen

4. 5BR Beach House, Game Room + Huge Backyard

5BR Beach House, Game Room + Huge Backyard
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (27 reviews)
"Very spacious and nicely decorated"
United States
Linda M.
5BR Beach House, Game Room + Huge Backyard
A living room with a sofa, armchair, ottoman, and coffee table.

5. Stamford Home | Family, Work and Plenty of Parking

Stamford Home | Family, Work and Plenty of 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 AED 764
AED 1,661 total
includes taxes & fees
9 Nov - 10 Nov
Stamford Home | Family, Work and Plenty of Parking
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

6. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.6 out of 10, Exceptional, (27 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 AED 3,162
AED 5,285 total
includes taxes & fees
27 Nov - 28 Nov
5BR Beach Home | Walk to Cove Beach + Private Yard
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

7. 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, (2 reviews)
"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 AED 5,061
AED 8,068 total
includes taxes & fees
9 Nov - 10 Nov
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A covered porch with wooden rocking chairs and a table, overlooking a body of water with boats and a bridge in the distance.

8. 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, (89 reviews)
"Comfortable beds and close to good food"
United States
Stacey S.
The price is AED 918
AED 1,968 total
includes taxes & fees
16 Nov - 17 Nov
Captain's Cottage - Cold Spring Harbor Water Views
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

9. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
8.0 out of 10, Very good, (20 reviews)
"Great location"
United States
Jordan S.
The price is AED 347
AED 426 total
includes taxes & fees
8 Nov - 9 Nov
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A modern kitchen with a marble island, bar stools, and a built-in oven.

10. 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 AED 837
AED 1,427 total
includes taxes & fees
8 Nov - 9 Nov
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A modern kitchen with white cabinets, a marble island, and black bar stools.

11. 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 AED 1,104
AED 2,467 total
includes taxes & fees
10 Nov - 11 Nov
Spacious Retreat with Game Room and Fire Pit
An outdoor patio with a fire pit, green chairs, and a table.

12. 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, (13 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is AED 486
AED 1,123 total
includes taxes & fees
11 Nov - 12 Nov
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

13. 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, (16 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 AED 893
AED 2,213 total
includes taxes & fees
9 Nov - 10 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

14. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is AED 1,267
AED 2,005 total
includes taxes & fees
8 Nov - 9 Nov
Gilded Age Luxury Surrounded by Nature
A modern outdoor patio with a seating area, a central table, and a large umbrella.

15. Mansion in Greenwich with private lake and river

Mansion in Greenwich with private lake and river
Greenwich
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful home. Exquisite decor and our kids enjoyed fishing right out back. Thoroughly enjoyed. "
United States
J.J. O.
The price is AED 14,508
AED 18,478 total
includes taxes & fees
14 Nov - 15 Nov
Mansion in Greenwich with private lake and river
A spacious living room with hardwood flooring, a beige sofa, a coffee table, and a dining area with a table and chairs.

16. Huntington Village 4BR Walkable Sleeps 8

Huntington Village 4BR Walkable Sleeps 8
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"The house was in an ideal location! Unfortunately, there was a nor easterner so walking was not an option but on a lovely day, it would be a perfect house to stay in and explore Huntington! The bedrooms were ideal."
United States
Susan
The price is AED 1,634
AED 2,917 total
includes taxes & fees
9 Nov - 10 Nov
Huntington Village 4BR Walkable Sleeps 8
A modern kitchen with granite countertops, stainless steel appliances, and white cabinetry.

17. Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
Huntington
9.2 out of 10, Wonderful, (12 reviews)
"Great place to stay"
United States
Michael D.
The price is AED 1,763
AED 2,438 total
includes taxes & fees
16 Nov - 17 Nov
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
A two-story house with a large front porch, a garage, and a well-maintained lawn.

18. The Victorian Blue 25min to NYC

The Victorian Blue 25min to NYC
North Side
9.8 out of 10, Exceptional, (9 reviews)
"Nice place very spacious and easy access to property. Clean and efficient"
United States
Sarah D.
The price is AED 3,409
AED 5,386 total
includes taxes & fees
7 Nov - 8 Nov
The Victorian Blue 25min to NYC
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

19. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AED 1,802
AED 3,748 total
includes taxes & fees
9 Nov - 10 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern living room with a large window, a sofa with patterned cushions, a wooden coffee table, and a painting on the wall.

20. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
United States
Karen O.
The price is AED 1,299
AED 2,844 total
includes taxes & fees
9 Nov - 10 Nov
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
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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Learn more about Old Greenwich

Spend sunny afternoons at Tod's Point Beach where locals gather for swimming and spectacular Long Island Sound views. Explore the charming village center with its independent shops, then head to nearby Greenwich Point Park for scenic coastal trails.

See all hotels in Old Greenwich
A calm lake with reflections of trees and a stone structure on the right.

Top reviews in Old Greenwich

A spacious atrium with a central bar, surrounded by seating areas and a circular water feature.
Hyatt Regency Greenwich

Hyatt Regency Greenwich

Hyatt Regency Greenwich
Old Greenwich

10/10 Excellent

Really nice rooms and beautiful lounge! Great food! Only issue I had was my tv didn't work (an engineer fixed it but within like 12 hours it wasn't working again) and when I went to the hot tub the jets weren't going so it was just like sitting in a hot bath. Still five stars because it's a great place for the price and the staff is all friendly and room service was delicious.
United States
Briana
Reviewed April 15, 2025
Hyatt Regency Greenwich

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