Ossining Vacations

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Find the Best Ossining Vacation Packages

Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
The price is ₩248,091 per night from Mar 1 to Mar 2
₩248,091
₩276,302 total
Mar 1 - Mar 2
includes taxes & fees
8.2/10 Very Good! (114 reviews)
Absolutely

Reviewed on Feb 21, 2026

Windrose On Hudson
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
The price is ₩195,223 per night from Mar 8 to Mar 9
₩195,223
₩223,287 total
Mar 8 - Mar 9
includes taxes & fees
8.2/10 Very Good! (1,574 reviews)
The staff was nice. My room was neat and clean. My problem with the place was the Wi-Fi. My stay was business related and I could not access my work laptop due to the firewall on my work computer not allowing me access due to safety concerns over WiFi access. This limited my ability to perform work. ...

Reviewed on Feb 21, 2026

Baymont by Wyndham White Plains - Elmsford
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is ₩152,798 per night from Mar 22 to Mar 23
₩152,798
₩177,817 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (1,078 reviews)
Clean comfortable room

Reviewed on Feb 23, 2026

DoubleTree by Hilton Hotel Nanuet
See all 1,324 properties in Ossining
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.

Discover the most popular places to visit in Ossining

Sing Sing Prison Museum

You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Sing Sing Prison Museum

Thomas J. Watson Research Center

Learn about the local history of Ossining with a stop at Thomas J. Watson Research Center. Stroll along the riverfront in this quaint area, or check out its top-notch restaurants.

Thomas J. Watson Research Center

Kitchawan Preserve

Explore the great outdoors at Kitchawan Preserve, a lovely green space in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Kitchawan Preserve

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.