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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Old Greenwich vacation 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, (20 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is AED 579
AED 1,194 total
includes taxes & fees
13 Oct - 14 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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
9.4 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.
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
Open concept kitchen

3. 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 AED 1,910
AED 3,921 total
includes taxes & fees
14 Oct - 15 Oct
5BR Beach House, Game Room + Huge Backyard
A campfire with a wooden table and benches by a lake.

4. 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 AED 628
AED 1,281 total
includes taxes & fees
11 Oct - 12 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

5. 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.
5BR Beach Home | Walk to Cove Beach + Private Yard
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 AED 1,759
AED 3,511 total
includes taxes & fees
14 Oct - 15 Oct
5BR Beach House, Water Views, Steps to Beach, Backyard
A living room with a sofa set, a coffee table, and a television on a stand.

7. 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 AED 1,146
AED 2,229 total
includes taxes & fees
14 Oct - 15 Oct
Spacious Stamford Home | Family, Work, Parking
A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

8. 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, (87 reviews)
"Comfortable beds and close to good food"
United States
Stacey S.
The price is AED 1,230
AED 2,329 total
includes taxes & fees
20 Oct - 21 Oct
Captain's Cottage - Cold Spring Harbor Water Views
A modern kitchen with white cabinets, a marble island, and black bar stools.

9. 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 AED 1,488
AED 3,049 total
includes taxes & fees
9 Nov - 10 Nov
Spacious Retreat with Game Room and Fire Pit
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 AED 918
AED 1,679 total
includes taxes & fees
12 Oct - 13 Oct
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

11. 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 AED 5,091
AED 8,477 total
includes taxes & fees
12 Oct - 13 Oct
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
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)
The price is AED 347
AED 495 total
includes taxes & fees
12 Oct - 13 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
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 AED 1,039
AED 2,482 total
includes taxes & fees
9 Nov - 10 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
An outdoor patio with a fire pit, green chairs, and a table.

14. 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, (11 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is AED 547
AED 1,298 total
includes taxes & fees
20 Oct - 21 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
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, (4 reviews)
"Beautiful, clean home with plenty of space for a large family to fit comfortably. Close to plenty of restaurants and a beautiful park. The host was quick to respond to all our questions. Highly recommend booking this place."
United States
Corinne J.
The price is AED 2,068
AED 3,592 total
includes taxes & fees
9 Nov - 10 Nov
Huntington Village 4BR Walkable Sleeps 8
A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

16. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is AED 859
AED 1,580 total
includes taxes & fees
12 Oct - 13 Oct
Gilded Age Luxury Surrounded by Nature
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
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 AED 1,818
AED 3,054 total
includes taxes & fees
10 Oct - 11 Oct
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
A modern kitchen with granite countertops, stainless steel appliances, and white cabinetry.

18. 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 AED 1,488
AED 2,207 total
includes taxes & fees
15 Oct - 16 Oct
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

19. 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 AED 1,330
AED 2,035 total
includes taxes & fees
10 Oct - 11 Oct
Luxury 3 BR Near NYC with Easy Parking
A room with a wooden door, a small table with a vase, and a chair.

20. 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 AED 1,961
AED 3,253 total
includes taxes & fees
22 Oct - 23 Oct
Spacious 3b/3b Mediterranean in White Plains
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

J House Greenwich

J House Greenwich

10/10 Excellent
"Rooms were clean, check- in was easy Staff was excellent , breakfast was great Tony’s restaurant was over the top so was Tony!! Over all great experience Would definitely stay again"
Sarah 1-night trip
Posted less than an hour ago
J House Greenwich

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