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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 backyardWaterside
10.0 out of 10, Exceptional, (21 reviews)
The price is ¥35,539
¥70,458 total
includes taxes & fees
Nov 10 - Nov 11

2. Spacious 3BR Townhome | Garage + Near Downtown
Spacious 3BR Townhome | Garage + Near DowntownWest Side
9.2 out of 10, Wonderful, (9 reviews)
The price is ¥48,495
¥92,616 total
includes taxes & fees
Nov 11 - Nov 12

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)
The price is ¥27,813
¥53,539 total
includes taxes & fees
Nov 10 - Nov 11

4. 5BR Beach House, Game Room + Huge Backyard
5BR Beach House, Game Room + Huge BackyardCove - East Side - Shippan
10.0 out of 10, Exceptional, (27 reviews)
The price is ¥70,524
¥146,108 total
includes taxes & fees
Dec 6 - Dec 7

5. Stamford Home | Family, Work and Plenty of Parking
Stamford Home | Family, Work and Plenty of ParkingCove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
The price is ¥30,864
¥69,091 total
includes taxes & fees
Nov 10 - Nov 11

6. 5BR Beach House | Water Views + Sauna + Game Room
5BR Beach House | Water Views + Sauna + Game RoomCove - East Side - Shippan
9.4 out of 10, Exceptional, (32 reviews)
The price is ¥70,365
¥138,405 total
includes taxes & fees
Nov 15 - Nov 16

7. 5BR Beach Home | Walk to Cove Beach + Private Yard
5BR Beach Home | Walk to Cove Beach + Private YardCove - East Side - Shippan
9.6 out of 10, Exceptional, (27 reviews)
The price is ¥122,030
¥204,855 total
includes taxes & fees
Nov 27 - Nov 28

8. Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic ViewsGreenwich
10.0 out of 10, Exceptional, (2 reviews)
The price is ¥218,385
¥348,133 total
includes taxes & fees
Nov 10 - Nov 11

9. Captain's Cottage - Cold Spring Harbor Water Views
Captain's Cottage - Cold Spring Harbor Water ViewsCold Spring Harbor
10.0 out of 10, Exceptional, (89 reviews)
The price is ¥38,828
¥83,835 total
includes taxes & fees
Nov 16 - Nov 17

10. Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Nice Cozy Room By Empire City Casino And Cross County Shopping CenterSoutheast Yonkers
8.0 out of 10, Very good, (20 reviews)
The price is ¥14,976
¥19,876 total
includes taxes & fees
Nov 10 - Nov 11

11. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Charming suite with patio, heating, WiFi, free parking in welcoming New RochelleNew Rochelle
10.0 out of 10, Exceptional, (14 reviews)
The price is ¥20,254
¥49,630 total
includes taxes & fees
Nov 16 - Nov 17

12. Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Ultra-Modern Studio | Near Hospital & NYCIM | WiFiHuntington
10.0 out of 10, Exceptional, (5 reviews)
The price is ¥36,133
¥64,460 total
includes taxes & fees
Nov 28 - Nov 29

13. Spacious Retreat with Game Room and Fire Pit
Spacious Retreat with Game Room and Fire PitWest Norwalk
9.4 out of 10, Exceptional, (3 reviews)
The price is ¥46,783
¥105,314 total
includes taxes & fees
Nov 10 - Nov 11

14. 3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQCranbury
8.8 out of 10, Excellent, (8 reviews)
The price is ¥46,752
¥92,434 total
includes taxes & fees
Nov 10 - Nov 11

15. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport BorderHistoric District
10.0 out of 10, Exceptional, (16 reviews)
The price is ¥38,653
¥95,649 total
includes taxes & fees
Nov 10 - Nov 11

16. Mansion in Greenwich with private lake and river
Mansion in Greenwich with private lake and riverGreenwich
9.8 out of 10, Exceptional, (6 reviews)
The price is ¥625,996
¥831,030 total
includes taxes & fees
Nov 14 - Nov 15

17. Gilded Age Luxury Surrounded by Nature
Gilded Age Luxury Surrounded by NatureCranbury
The price is ¥54,676
¥87,481 total
includes taxes & fees
Nov 19 - Nov 20

18. Huntington Village 4BR Walkable Sleeps 8
Huntington Village 4BR Walkable Sleeps 8Huntington
10.0 out of 10, Exceptional, (5 reviews)
The price is ¥70,524
¥125,841 total
includes taxes & fees
Nov 10 - Nov 11

19. Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington VillageHuntington
9.2 out of 10, Wonderful, (12 reviews)
The price is ¥68,463
¥95,785 total
includes taxes & fees
Nov 16 - Nov 17

20. Stareway to Heaven Su
Stareway to Heaven SuFairfield Beach
10.0 out of 10, Exceptional, (25 reviews)
The price is ¥122,822
¥166,562 total
includes taxes & fees
Nov 24 - Nov 25
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.
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.













































































































































