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Holiday Homes in Old Greenwich

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Old Greenwich holiday homes

A patio with outdoor furniture, a grill, and potted plants.

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)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is €400
includes taxes & fees
25 Oct - 26 Oct
Gem by the water+ firepit and all fenced backyard
A modern living room with a white sofa, a glass coffee table, and a piano.

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

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.2 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 €558
includes taxes & fees
27 Oct - 28 Oct
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

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, (45 reviews)
"Nice stay"
United States
Christopher J.
The price is €335
includes taxes & fees
25 Oct - 26 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Open concept kitchen

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)
"Very spacious and nicely decorated"
United States
Linda M.
The price is €787
includes taxes & fees
27 Oct - 28 Oct
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 €453
includes taxes & fees
26 Oct - 27 Oct
Spacious Stamford Home | Family, Work, Parking
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.

6. 5BR Beach House, Water Views, Steps to Beach, Backyard

5BR Beach House, Water Views, Steps to Beach, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 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 €878
includes taxes & fees
1 Nov - 2 Nov
5BR Beach House, Water Views, Steps to Beach, Backyard
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

7. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 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 €605
includes taxes & fees
28 Oct - 29 Oct
5BR Beach Home | Walk to Cove Beach + Private Yard
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

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 €2,175
includes taxes & fees
3 Nov - 4 Nov
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

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, (88 reviews)
"Comfortable beds and close to good food"
United States
Stacey S.
The price is €439
includes taxes & fees
26 Oct - 27 Oct
Captain's Cottage - Cold Spring Harbor Water Views
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 €410
includes taxes & fees
22 Oct - 23 Oct
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A modern kitchen with white cabinets, a marble island, and black bar stools.

11. 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 €686
includes taxes & fees
18 Nov - 19 Nov
Spacious Retreat with Game Room and Fire Pit
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

12. 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 €124
includes taxes & fees
27 Oct - 28 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
An outdoor patio with a fire pit, green chairs, and a table.

13. 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, (12 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is €320
includes taxes & fees
27 Oct - 28 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

14. 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 €596
includes taxes & fees
9 Nov - 10 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A living room with a sofa, a coffee table, a wicker chair, a ceiling fan, and a large window with a view of a parked car outside.

15. 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 €731
includes taxes & fees
27 Oct - 28 Oct
Huntington Village 4BR Walkable Sleeps 8
A bedroom with a wooden staircase, two beds, a nightstand, and a wall-mounted lamp.

16. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is €501
includes taxes & fees
22 Oct - 23 Oct
Gilded Age Luxury Surrounded by Nature
A modern outdoor patio with a seating area, a central table, and a large umbrella.

17. 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.
Mansion in Greenwich with private lake and river
A room with a wooden door, a small table with a vase, and a chair.

18. Spacious 3b/3b Mediterranean in White Plains

Spacious 3b/3b Mediterranean in White Plains
White Plains
9.4 out of 10, Exceptional, (18 reviews)
"This was a wonderful property. It was very charming and had everything we could need. Great neighborhood, lots of room very comfortable. We would definitely stay there again. Great host response!"
United States
Nancy K.
The price is €782
includes taxes & fees
22 Oct - 23 Oct
Spacious 3b/3b Mediterranean in White Plains
A modern kitchen with granite countertops, stainless steel appliances, and white cabinetry.

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 €554
includes taxes & fees
28 Oct - 29 Oct
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
A room with two beds, white curtains, a ceiling light, and a window with a view.

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

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
2.0 out of 10, (1 review)
"This guy is a scammer, an hour before my checkin they finally sent me the "location" and claimed they needed more time to clean the property. Then at 5 pm and hour after they claimed their was a gas leak and I couldn't stay there. Only thing is the address they sent me wasn't real and I am convinced this listing is fake in and used to trick people into staying at their actual property in yonkers. DO NOT RENT FROM THEM!"
United States
Ethan G.
The price is €748
includes taxes & fees
22 Oct - 23 Oct
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
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

Sonesta White Plains Downtown

Sonesta White Plains Downtown

10/10 Excellent
"What a surprise! I was looking for something close to Westchester airport (10 mins) and did not expect this to be as great as it was."
Nicole 1-night trip
Posted 2 hours ago
Sonesta White Plains Downtown

Find out more about Old Greenwich

Old Greenwich Holiday Homes information

Number of reviews
327
Accommodation
230 Holiday Homes
Lowest Price
€124
Highest Price
€2,175