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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 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, (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.
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 1,914
AED 3,925 total
includes taxes & fees
14 Oct - 15 Oct
5BR Beach House, Game Room + Huge Backyard
A modern living room with a white sofa, a glass coffee table, and a piano.

4. 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 AED 1,212
AED 2,347 total
includes taxes & fees
28 Oct - 29 Oct
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
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.
The price is AED 1,050
AED 2,634 total
includes taxes & fees
14 Oct - 15 Oct
5BR Beach Home | Walk to Cove Beach + Private Yard
A living room with a sofa set, a coffee table, and a television on a stand.

6. 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 1,164
AED 2,254 total
includes taxes & fees
14 Oct - 15 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.

7. 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)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is AED 1,634
AED 3,359 total
includes taxes & fees
14 Oct - 15 Oct
5BR Beach House, Water Views, Steps to Beach, Backyard
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, (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 4,889
AED 8,146 total
includes taxes & fees
17 Oct - 18 Oct
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

9. 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 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 lakeside view with boats docked, surrounded by autumn-colored trees and houses.

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, (87 reviews)
"Comfortable beds and close to good food"
United States
Stacey S.
The price is AED 1,249
AED 2,350 total
includes taxes & fees
20 Oct - 21 Oct
Captain's Cottage - Cold Spring Harbor Water Views
An outdoor patio with a fire pit, green chairs, and a table.

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, (11 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is AED 544
AED 1,302 total
includes taxes & fees
13 Oct - 14 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.

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 AED 918
AED 1,679 total
includes taxes & fees
12 Oct - 13 Oct
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A modern kitchen with white cabinets, a marble island, and black bar stools.

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 AED 1,399
AED 2,962 total
includes taxes & fees
28 Oct - 29 Oct
Spacious Retreat with Game Room and Fire Pit
A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

14. 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 modern living room with a fireplace, a television, and a dining area with chairs and a table.

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, (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 1,205
AED 2,683 total
includes taxes & fees
5 Nov - 6 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A house with a white exterior, a brown roof, and a balcony. It is located on stilts over water, surrounded by dense green trees.

16. Waterfront Studio Beach Cottage Wow Sunsets Walk to Village Shops Winery Brewery

Waterfront Studio Beach Cottage Wow Sunsets Walk to Village Shops Winery Brewery
Northport
9.2 out of 10, Wonderful, (22 reviews)
"Great host and property!"
United States
Anonymous traveler
The price is AED 3,295
AED 5,355 total
includes taxes & fees
12 Oct - 13 Oct
Waterfront Studio Beach Cottage Wow Sunsets Walk to Village Shops Winery Brewery
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.

17. 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 1,712
AED 3,168 total
includes taxes & fees
19 Oct - 20 Oct
Huntington Village 4BR Walkable Sleeps 8
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 1,421
AED 2,119 total
includes taxes & fees
14 Oct - 15 Oct
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
A room with a wooden door, a small table with a vase, and a chair.

19. 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
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 AED 1,818
AED 3,054 total
includes taxes & fees
9 Oct - 10 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

Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"This is a budget hotel done right. Incredibly helpful staff (thank you Tangi!), clean and comfortable room and ample parking. I would stay here again without hesitation."
Mary 1-night trip
Posted less than an hour ago
Amsterdam Hotel

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