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

Holiday Homes in Old Greenwich

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Old Greenwich holiday homes

A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

1. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (18 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is AU$539
includes taxes & fees
20 Sept - 21 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A campfire with a wooden table and benches by a lake.

2. 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, (42 reviews)
"This is a beautiful property. Great location. And the hosts are very nice and very great in communicating everything. Loved staying there"
United States
Martina F.
The price is AU$554
includes taxes & fees
20 Sept - 21 Sept
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A living room with a piano, a white sofa, a coffee table, and a lamp.

3. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.4 out of 10, Exceptional, (8 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 AU$1,075
includes taxes & fees
8 Sept - 9 Sept
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

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, (26 reviews)
"Great stay!"
United States
Kyra S.
The price is AU$1,278
includes taxes & fees
7 Sept - 8 Sept
5BR Beach House, Game Room + Huge Backyard
A living room with a sofa set, a coffee table, and a television on a stand.

5. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, 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 AU$812
includes taxes & fees
9 Sept - 10 Sept
Spacious Stamford Home | Family, Work, Parking
A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

6. 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, (84 reviews)
"A beautiful home and you cannot beat the views and location!"
United States
Daniel M.
The price is AU$756
includes taxes & fees
9 Sept - 10 Sept
Captain's Cottage - Cold Spring Harbor Water Views
A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

7. 5BR Beach House, Water Views, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is AU$1,327
includes taxes & fees
22 Sept - 23 Sept
5BR Beach House, Water Views, Game Room, Backyard
A modern living room with a large window offering a cityscape view, a blue sofa, a small side table, and a flat-screen TV.

8. The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace

The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace
Cove - East Side - Shippan
9.0 out of 10, Wonderful, (10 reviews)
"Beautiful place, very clean. Great Host!"
United States
Alejandro A.
The price is AU$1,448
includes taxes & fees
7 Sept - 8 Sept
The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace
An outdoor patio with a fire pit, green chairs, and a table.

9. 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
9.8 out of 10, Exceptional, (9 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is AU$477
includes taxes & fees
5 Oct - 6 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A modern kitchen with a marble island, bar stools, and a built-in oven.

10. 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 AU$616
includes taxes & fees
9 Sept - 10 Sept
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A living room with a sofa, a glass coffee table, a fireplace, and a television.

11. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is AU$582
includes taxes & fees
29 Sept - 30 Sept
Gilded Age Luxury Surrounded by Nature
A modern kitchen with white cabinets, a marble island, and black bar stools.

12. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
10.0 out of 10, Exceptional, (2 reviews)
"A great location. We were less than 15 minutes from everything we did. House was a super layout for our large group."
United States
Mark F.
The price is AU$1,080
includes taxes & fees
9 Sept - 10 Sept
Spacious Retreat with Game Room and Fire Pit
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

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, (15 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 AU$1,016
includes taxes & fees
30 Sept - 1 Oct
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

14. 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, (1 review)
"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 AU$4,025
includes taxes & fees
21 Sept - 22 Sept
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

15. 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 AU$190
includes taxes & fees
15 Sept - 16 Sept
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

16. Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is AU$519
includes taxes & fees
7 Sept - 8 Sept
Luxury 3 BR Near NYC with Easy Parking
A room with two beds, white curtains, a ceiling light, and a window with a view.

17. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
The price is AU$760
includes taxes & fees
6 Sept - 7 Sept
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
A modern living room with a white sofa, a glass coffee table, and a marble-patterned rug.

18. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
4.6 out of 10, (11 reviews)
"Don’t stay here. Not as listed. "
United States
Kenyon
The price is AU$595
includes taxes & fees
7 Sept - 8 Sept
Modern Luxury Home w GameRoom & Parking
A wooden deck with chairs and a kayak, leading to a beach with a view of the ocean.

19. Shore to Shore Coastal Retreat at Asharoken

Shore to Shore Coastal Retreat at Asharoken
Northport
The price is AU$1,559
includes taxes & fees
8 Sept - 9 Sept
Shore to Shore Coastal Retreat at Asharoken
A modern kitchen with granite countertops, stainless steel appliances, and white cabinetry.

20. 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 location & thoughtful amenities."
United States
Joshua
The price is AU$934
includes taxes & fees
5 Oct - 6 Oct
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
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

Tarrytown House Estate

Tarrytown House Estate

8/10 Good
"Room was spacious and clean but no microwave in my room."
Michael 1-night trip
Posted 8 hours ago
Tarrytown House Estate

Find out more about Old Greenwich

Old Greenwich Holiday Homes information

Number of reviews
268
Accommodation
285 Holiday Homes
Lowest Price
AU$190
Highest Price
AU$4,025