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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 ¥35,539
¥70,458 total
includes taxes & fees
Nov 10 - Nov 11
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 ¥48,495
¥92,616 total
includes taxes & fees
Nov 11 - Nov 12
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 ¥27,813
¥53,539 total
includes taxes & fees
Nov 10 - Nov 11
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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.
The price is ¥70,524
¥146,108 total
includes taxes & fees
Dec 6 - Dec 7
5BR Beach House, Game Room + Huge Backyard

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 ¥30,864
¥69,091 total
includes taxes & fees
Nov 10 - Nov 11
Stamford Home | Family, Work and Plenty of Parking

6. 5BR Beach House | Water Views + Sauna + Game Room

5BR Beach House | Water Views + Sauna + Game Room
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 ¥70,365
¥138,405 total
includes taxes & fees
Nov 15 - Nov 16
5BR Beach House | Water Views + Sauna + Game Room

7. 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 ¥122,030
¥204,855 total
includes taxes & fees
Nov 27 - Nov 28
5BR Beach Home | Walk to Cove Beach + Private Yard

8. 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 ¥218,385
¥348,133 total
includes taxes & fees
Nov 10 - Nov 11
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

9. 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 ¥38,828
¥83,835 total
includes taxes & fees
Nov 16 - Nov 17
Captain's Cottage - Cold Spring Harbor Water Views

10. 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 ¥14,976
¥19,876 total
includes taxes & fees
Nov 10 - Nov 11
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

11. 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, (14 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is ¥20,254
¥49,630 total
includes taxes & fees
Nov 16 - Nov 17
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

12. 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 ¥36,133
¥64,460 total
includes taxes & fees
Nov 28 - Nov 29
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

13. 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 ¥46,783
¥105,314 total
includes taxes & fees
Nov 10 - Nov 11
Spacious Retreat with Game Room and Fire Pit

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, BBQ
Cranbury
8.8 out of 10, Excellent, (8 reviews)
"Great spot for our family. "
United States
Kevin I.
The price is ¥46,752
¥92,434 total
includes taxes & fees
Nov 10 - Nov 11
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ

15. 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 ¥38,653
¥95,649 total
includes taxes & fees
Nov 10 - Nov 11
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

16. 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 ¥625,996
¥831,030 total
includes taxes & fees
Nov 14 - Nov 15
Mansion in Greenwich with private lake and river

17. Gilded Age Luxury Surrounded by Nature

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

18. 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 ¥70,524
¥125,841 total
includes taxes & fees
Nov 10 - Nov 11
Huntington Village 4BR Walkable Sleeps 8

19. 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 ¥68,463
¥95,785 total
includes taxes & fees
Nov 16 - Nov 17
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

20. Stareway to Heaven Su

Stareway to Heaven Su
Fairfield Beach
10.0 out of 10, Exceptional, (25 reviews)
"Great property right on the beach!!!! Very clean and the perfect elevated stay for our weekend Would recommend this property again and again!!!"
United States
Amanda B.
The price is ¥122,822
¥166,562 total
includes taxes & fees
Nov 24 - Nov 25
Stareway to Heaven Su
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.

A calm lake with reflections of trees and a stone structure on the right.

Top reviews in Old Greenwich

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