A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Ossining cottages

House (5 Bedrooms) | Front of property

1. Nyc-area Escape Near River, Trails & Mta!

Nyc-area Escape Near River, Trails & Mta!
3.0 star property
Ossining
Nyc-area Escape Near River, Trails & Mta!
Property grounds

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, (145 reviews)
"We had a great stay!!"
United States
Jasmine
$269 nightly
The price is $318
Sep 22 - Sep 23
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

3. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$413 nightly
The price is $455
Sep 23 - Sep 24
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Property grounds

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, (13 reviews)
"Beautiful and restful"
United States
Lisa H.
$1,397 nightly
The price is $1,580
Sep 24 - Sep 25
Total with taxes and fees
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
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

Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"walking distance to downtown, nice staff, clean. great option for the price and location."
Karissa 1-night trip
Posted 2 hours ago
Amsterdam Hotel

Find out more about Ossining

Ossining Cottages information

Number of reviews
13,015
Accommodation
54 Cottages
Lowest Price
$112
Highest Price
$1,233

Frequently asked questions

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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 Center, 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.

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