Book Holiday Homes in Ossining Station
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Featured Holiday Homes in Ossining Station

Foliage at Westchester Manor - Near Sleepy Hollow
Ossining NY
Located in Ossining, this vacation home is within a 5-minute drive of Sing Sing Prison Museum and Sing Sing Correctional Facility.

Neighbor's house - Welcome!
Ossining NY
Located in Ossining, this vacation home is within a 5-minute drive of Ossining Historical Society and Sing Sing Correctional Facility.
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View all propertiesLowest 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.
Top trending hotels in Ossining Station

West Gate Inn Nyack
26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 26 Dec to 27 Dec
AU$206
26 Dec - 27 Dec
includes taxes & fees
Located in Nyack, West Gate Inn Nyack is within a 5-minute drive of Edward Hopper House Art Center and Memorial Park.

Hotel Nyack, a JdV by Hyatt Hotel
400 High Avenue Nyack NY
Fully refundableReserve now, pay when you stay
The price is AU$244 per night from 21 Dec to 22 Dec
AU$244
21 Dec - 22 Dec
includes taxes & fees
Located in Nyack, Hotel Nyack, a JdV by Hyatt Hotel is in the historical district, a 2-minute drive from Palisades Center and 9 minutes from Tarrytown Music ...

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
20 Saw Mill River Rd. Hawthorne NY
Fully refundable
The price is AU$244 per night from 9 Jan to 10 Jan
AU$244
9 Jan - 10 Jan 2026
includes taxes & fees
Located in Hawthorne, Holiday Inn Express & Suites Hawthorne Elmsford North by IHG is within a 5-minute drive of Captain Lawrence Brewing Company and Westchester ...
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Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
The price is AU$297 per night from 4 Jan to 5 Jan
AU$297
4 Jan - 5 Jan 2026
includes taxes & fees
Located in Ossining, Windrose On Hudson is in a rural location, within a 5-minute drive of Old Croton Aqueduct State Park and Van Cortlandt Manor.
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See all available properties in Ossining Station
View all propertiesLowest 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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