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Our top choices for Old Greenwich vacation homes

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 1,640 total
includes taxes & fees
3 Nov - 4 Nov
Gem by the water+ firepit and all fenced backyard

2. 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 1,033
AED 2,042 total
includes taxes & fees
3 Nov - 4 Nov
Spacious 3BR Townhome | Garage + Near Downtown

3. 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 628
AED 1,226 total
includes taxes & fees
3 Nov - 4 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

4. 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.
Stamford Home | Family, Work and Plenty of Parking

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

5BR Beach House, Game Room + Huge Backyard
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (26 reviews)
"Very spacious and nicely decorated"
United States
Linda M.
The price is AED 2,810
AED 5,067 total
includes taxes & fees
3 Nov - 4 Nov
5BR Beach House, Game Room + Huge Backyard

6. 5BR Beach House, Water Views, Steps to Beach, Backyard

5BR Beach House, Water Views, Steps to Beach, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (32 reviews)
"The property was amazing. The house was clean, beautiful, and well equipped. Plenty of space yet still cozy. Host was very communicative and gracious, had a pleasant experience and will definitely be back!"
United States
Maxx V.
The price is AED 2,369
AED 4,242 total
includes taxes & fees
11 Nov - 12 Nov
5BR Beach House, Water Views, Steps to Beach, Backyard

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 5,510
AED 8,621 total
includes taxes & fees
3 Nov - 4 Nov
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

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 1,084
AED 2,182 total
includes taxes & fees
8 Nov - 9 Nov
Captain's Cottage - Cold Spring Harbor Water Views

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
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is AED 347
AED 461 total
includes taxes & fees
3 Nov - 4 Nov
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

10. 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, (12 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

11. 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 1,494 total
includes taxes & fees
3 Nov - 4 Nov
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

12. 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 1,308
AED 2,767 total
includes taxes & fees
18 Nov - 19 Nov
Spacious Retreat with Game Room and Fire Pit

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 1,021
AED 2,427 total
includes taxes & fees
9 Nov - 10 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

14. 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.
Mansion in Greenwich with private lake and river

15. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is AED 1,267
AED 2,020 total
includes taxes & fees
3 Nov - 4 Nov
Gilded Age Luxury Surrounded by Nature

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 1,983
AED 3,349 total
includes taxes & fees
16 Nov - 17 Nov
Huntington Village 4BR Walkable Sleeps 8

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 1,587
AED 2,220 total
includes taxes & fees
9 Nov - 10 Nov
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

18. Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.

Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.
Hicksville
9.6 out of 10, Exceptional, (4 reviews)
"My family and I absolutely loved this home! It had everything we needed and plenty of room for everyone! We def recommend this home"
United States
Erin D.
The price is AED 2,743
AED 4,637 total
includes taxes & fees
3 Nov - 4 Nov
Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.

19. 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 2,098
AED 3,640 total
includes taxes & fees
8 Nov - 9 Nov
The Victorian Blue 25min to NYC

20. Spacious 4-bedroom house in charming Hicksville with AC

Spacious 4-bedroom house in charming Hicksville with AC
Downtown Hicksville
10.0 out of 10, Exceptional, (4 reviews)
"Perfect place for our family stay, and the listing was exactly as advertised."
United States
Kevin D.
The price is AED 2,624
AED 4,491 total
includes taxes & fees
3 Nov - 4 Nov
Spacious 4-bedroom house in charming Hicksville with AC
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

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