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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, (22 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is ¥35,815
¥71,006 total
includes taxes & fees
Nov 17 - Nov 18
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 ¥43,920
¥87,161 total
includes taxes & fees
Nov 16 - Nov 17
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 ¥27,406
¥53,237 total
includes taxes & fees
Nov 18 - Nov 19
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

4. 5BR Beach Home w/ Fireplaces, Fire Pit & Game Room

5BR Beach Home w/ Fireplaces, Fire Pit & Game Room
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (27 reviews)
"Very spacious and nicely decorated"
United States
Linda M.
The price is ¥74,744
¥159,116 total
includes taxes & fees
Nov 19 - Nov 20
5BR Beach Home w/ Fireplaces, Fire Pit & Game Room

5. Spacious 3BR | Family + Work | Ample Parking

Spacious 3BR | Family + Work | Ample Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"Great location - very spacious and strong AC! host was very communicative and easy to deal with."
United States
Cari B.
The price is ¥37,212
¥76,972 total
includes taxes & fees
Nov 16 - Nov 17
Spacious 3BR | Family + Work | Ample Parking

6. 5BR Water View Home, Sauna, Game Room, Fire Pit

5BR Water View Home, Sauna, Game Room, Fire Pit
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 ¥89,917
¥168,411 total
includes taxes & fees
Dec 2 - Dec 3
5BR Water View Home, Sauna, Game Room, Fire Pit

7. Coastal 5BR: Billiards, Ping Pong, Fire Pit, Yard

Coastal 5BR: Billiards, Ping Pong, Fire Pit, 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 ¥79,056
¥154,845 total
includes taxes & fees
Nov 16 - Nov 17
Coastal 5BR: Billiards, Ping Pong, Fire Pit, Yard

8. Private Single Fam, walk 2 train/ Theater- Dogs OK

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

9. 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 ¥223,275
¥354,828 total
includes taxes & fees
Nov 18 - Nov 19
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

10. 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 ¥32,741
¥76,093 total
includes taxes & fees
Nov 17 - Nov 18
Captain's Cottage - Cold Spring Harbor Water Views

11. 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 ¥12,649
¥17,154 total
includes taxes & fees
Nov 16 - Nov 17
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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, (14 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is ¥20,411
¥46,180 total
includes taxes & fees
Nov 16 - Nov 17
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

13. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
8.6 out of 10, Excellent, (4 reviews)
"We had a wonderful stay."
United States
Linda S.
The price is ¥56,489
¥120,391 total
includes taxes & fees
Nov 18 - Nov 19
Spacious Retreat with Game Room and Fire Pit

14. 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 ¥36,414
¥64,961 total
includes taxes & fees
Dec 1 - Dec 2
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

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 ¥41,828
¥102,253 total
includes taxes & fees
Nov 17 - Nov 18
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

16. Gilded Age Luxury Surrounded by Nature

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

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, BBQ
Cranbury
8.8 out of 10, Excellent, (8 reviews)
"Great spot for our family. "
United States
Kevin I.
The price is ¥47,114
¥93,470 total
includes taxes & fees
Nov 19 - Nov 20
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ

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 ¥71,071
¥126,818 total
includes taxes & fees
Nov 19 - Nov 20
Huntington Village 4BR Walkable Sleeps 8

19. Stareway to Heaven in Fairfield

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

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 ¥98,541
¥140,864 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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