A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Ossining cottages

A wooden deck with a railing overlooking a body of water and trees.

1. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is NZ$698
includes taxes & fees
17 Nov - 18 Nov
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A house with a view of a bridge and mountains.

2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (150 reviews)
"We had a great stay!!"
United States
Jasmine
The price is NZ$551
includes taxes & fees
7 Dec - 8 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A deck with wicker furniture overlooking a river.

3. Historic, private riverfront cottage in peaceful Greenwich

Historic, private riverfront cottage in peaceful Greenwich
Greenwich
The price is NZ$649
includes taxes & fees
17 Nov - 18 Nov
Historic, private riverfront cottage in peaceful Greenwich
A wooden house with a stone pathway leading to a wooden deck.

4. Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is NZ$2,671
includes taxes & fees
16 Nov - 17 Nov
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
A wooden deck with a railing overlooking a well-maintained lawn and trees.

5. Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
9.8 out of 10, Exceptional, (11 reviews)
"Beautiful setting, and plenty of room for a family of four. Accommodations were very clean and spacious. Thank you for hosting us!"
United States
Susan K.
The price is NZ$1,206
includes taxes & fees
29 Nov - 30 Nov
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
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 Ossining Hotel Reviews

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

10/10 Excellent
"It was very nice to stay there I slept like a baby till next time"
Jean 1-night trip
Posted 2 hours ago
LIV Hotel Bronx - Newly Built

Find out more about Ossining

Ossining Cottages information

Number of reviews
204
Accommodation
46 Cottages
Lowest Price
NZ$551
Highest Price
NZ$2,671

Frequently asked questions

What is there to do in Ossining near my cottage?
Ossining has enough experiences to keep you going for weeks, beginning with Sing Sing Correctional Facility. Thomas J. Watson Research Centre, Louis Engel Waterfront Park and Ossining Historical Society are other awesome attractions. If you're lingering longer, Sing Sing Prison Museum and Teatown Lake Reservation will cap off your itinerary nicely.