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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, (22 reviews)
The price is ¥35,815
¥71,006 total
includes taxes & fees
Nov 17 - Nov 18

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 ¥43,920
¥87,161 total
includes taxes & fees
Nov 16 - Nov 17

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 ¥27,406
¥53,237 total
includes taxes & fees
Nov 18 - Nov 19

4. 5BR Beach Home w/ Fireplaces, Fire Pit & Game Room
5BR Beach Home w/ Fireplaces, Fire Pit & Game RoomCove - East Side - Shippan
10.0 out of 10, Exceptional, (27 reviews)
The price is ¥74,744
¥159,116 total
includes taxes & fees
Nov 19 - Nov 20

5. Spacious 3BR | Family + Work | Ample Parking
Spacious 3BR | Family + Work | Ample ParkingCove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
The price is ¥37,212
¥76,972 total
includes taxes & fees
Nov 16 - Nov 17

6. 5BR Water View Home, Sauna, Game Room, Fire Pit
5BR Water View Home, Sauna, Game Room, Fire PitCove - East Side - Shippan
9.4 out of 10, Exceptional, (32 reviews)
The price is ¥89,917
¥168,411 total
includes taxes & fees
Dec 2 - Dec 3

7. Coastal 5BR: Billiards, Ping Pong, Fire Pit, Yard
Coastal 5BR: Billiards, Ping Pong, Fire Pit, YardCove - East Side - Shippan
9.6 out of 10, Exceptional, (27 reviews)
The price is ¥79,056
¥154,845 total
includes taxes & fees
Nov 16 - Nov 17

8. Private Single Fam, walk 2 train/ Theater- Dogs OK
Private Single Fam, walk 2 train/ Theater- Dogs OKGreenwich
The price is ¥37,104
¥122,863 total
includes taxes & fees
Dec 6 - Dec 7

9. 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 ¥223,275
¥354,828 total
includes taxes & fees
Nov 18 - Nov 19

10. 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 ¥32,741
¥76,093 total
includes taxes & fees
Nov 17 - Nov 18

11. 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 ¥12,649
¥17,154 total
includes taxes & fees
Nov 16 - Nov 17

12. 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 ¥20,411
¥46,180 total
includes taxes & fees
Nov 16 - Nov 17

13. Spacious Retreat with Game Room and Fire Pit
Spacious Retreat with Game Room and Fire PitWest Norwalk
8.6 out of 10, Excellent, (4 reviews)
The price is ¥56,489
¥120,391 total
includes taxes & fees
Nov 18 - Nov 19

14. 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 ¥36,414
¥64,961 total
includes taxes & fees
Dec 1 - Dec 2

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 ¥41,828
¥102,253 total
includes taxes & fees
Nov 17 - Nov 18

16. Gilded Age Luxury Surrounded by Nature
Gilded Age Luxury Surrounded by NatureCranbury
The price is ¥35,631
¥64,654 total
includes taxes & fees
Nov 18 - Nov 19

17. 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 ¥47,114
¥93,470 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 ¥71,071
¥126,818 total
includes taxes & fees
Nov 19 - Nov 20

19. Stareway to Heaven in Fairfield
Stareway to Heaven in FairfieldFairfield Beach
The price is ¥114,382
¥172,680 total
includes taxes & fees
Nov 24 - Nov 25

20. Stareway to Heaven Su
Stareway to Heaven SuFairfield Beach
10.0 out of 10, Exceptional, (25 reviews)
The price is ¥98,541
¥140,864 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.









































































































































