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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Ossining cottages

Exterior

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is £362
includes taxes & fees
14 Apr - 15 Apr
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Property grounds

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, (134 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is £203
includes taxes & fees
13 Apr - 14 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
House (3 Bedrooms) | Interior

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is £416
includes taxes & fees
15 Apr - 16 Apr
Updated Home w/ Patio Half Mile to West Point
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

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

10/10 Excellent
"Clean room"
Robert 2-night trip
Posted 2 hours ago
Baymont by Wyndham White Plains - Elmsford

Find out more about Ossining

Ossining Cottages information

Number of reviews
157
Accommodation
49 Cottages
Lowest Price
£203
Highest Price
£416

Frequently asked questions

Why book your cottage in Ossining with Expedia?
We think that holidays should be a walk in the park, so if you're chasing cottages in Ossining at an affordable price, Expedia can help. Stick to the budget and go for a wallet-friendly option surrounded by wilderness, or splurge on an upmarket cottage to spoil your favourite people.
How can I find cheap cottages in Ossining?
Expedia is here to help you look for cheap cottages in Ossining. To book the perfect stay in just a few clicks, try out the filter tool to refine your search results by budget, amenities and star rating.
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.