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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Ossining guest houses

An aerial view of a campus with multiple buildings, a central courtyard, and a lake in the background.

1. Near NYC! | Stylish Guestroom

Near NYC! | Stylish Guestroom
Ossining
The price is NZ$569
includes taxes & fees
15 Nov - 16 Nov
Near NYC! | Stylish Guestroom
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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Learn more about Ossining

Sing Sing Prison Museum offers a fascinating glimpse into America's most notorious correctional facility, with guided tours by former officers. Hike the scenic Old Croton Aqueduct Trail and then grab lunch at one of the diverse restaurants along the Hudson River waterfront.

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A wooden bridge over a lake with a sign reading "BERGMANN BOARDWALK".