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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Old Greenwich vacation homes

A bedroom with a bed, bedside tables, a mirror, a wardrobe, and a painting on the wall.

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 AED 824
AED 1,714 total
includes taxes & fees
20 Oct - 21 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.
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 AED 698
AED 1,361 total
includes taxes & fees
15 Nov - 16 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A living room with a sofa set, a coffee table, and a television on a stand.

4. 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 1,073
AED 2,133 total
includes taxes & fees
1 Nov - 2 Nov
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.

5. 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 1,840
AED 3,611 total
includes taxes & fees
1 Nov - 2 Nov
5BR Beach House, Water Views, Steps to Beach, Backyard
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, (87 reviews)
"Comfortable beds and close to good food"
United States
Stacey S.
The price is AED 863
AED 1,897 total
includes taxes & fees
27 Oct - 28 Oct
Captain's Cottage - Cold Spring Harbor Water Views
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

7. 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 AED 5,510
AED 8,940 total
includes taxes & fees
20 Oct - 21 Oct
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

8. 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
19 Oct - 20 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A modern kitchen with a marble island, bar stools, and a built-in oven.

9. 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
19 Oct - 20 Oct
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A modern kitchen with white cabinets, a marble island, and black bar stools.

10. 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 1,260
AED 2,754 total
includes taxes & fees
18 Nov - 19 Nov
Spacious Retreat with Game Room and Fire Pit
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, (12 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is AED 540
AED 1,290 total
includes taxes & fees
9 Nov - 10 Nov
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.

12. 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 999
AED 2,429 total
includes taxes & fees
9 Nov - 10 Nov
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A bedroom with a wooden staircase, two beds, a nightstand, and a wall-mounted lamp.

13. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
The price is AED 1,267
AED 2,072 total
includes taxes & fees
19 Oct - 20 Oct
Gilded Age Luxury Surrounded by Nature
A modern outdoor patio with a seating area, a central table, and a large umbrella.

14. 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 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 AED 1,877
AED 3,345 total
includes taxes & fees
17 Nov - 18 Nov
Huntington Village 4BR Walkable Sleeps 8
A room with a wooden door, a small table with a vase, and a chair.

16. 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 modern kitchen with granite countertops, stainless steel appliances, and white cabinetry.

17. 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 1,763
AED 2,535 total
includes taxes & fees
16 Nov - 17 Nov
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.

18. 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
25 Oct - 26 Oct
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
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
2.0 out of 10, (1 review)
"This is a scam and at the same time others guest’s was there for same booking but we can’t get any feed the property support and we returned from the property and kids suffered a lot!!!"
United States
Md Asadul
The price is AED 1,330
AED 2,035 total
includes taxes & fees
19 Oct - 20 Oct
Luxury 3 BR Near NYC with Easy Parking
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

20. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
Ossining
8.2 out of 10, Very good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
The price is AED 804
AED 2,900 total
includes taxes & fees
21 Oct - 22 Oct
Snow Days & City Escapes: Spacious Ossining Home
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

Hilltop Inn & Suites

Hilltop Inn & Suites

8/10 Good
"I had a place to sleep after I party for my birthday and it was at a reasonable price"
Raven 1-night trip
Posted less than an hour ago
Hilltop Inn & Suites

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