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 ₩247,315 per night from Mar 3 to Mar 4
₩247,315
₩275,447 total
Mar 3 - Mar 4
includes taxes & fees
8.4/10 Very Good! (116 reviews)
Amazing staff, from front desk Nelson to the cleaning crew, everyone was amazing! Nice facilities, awesome gym, loved our stay

Reviewed on Feb 27, 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 ₩193,388 per night from Mar 30 to Mar 31
₩193,388
₩221,188 total
Mar 30 - Mar 31
includes taxes & fees
8.2/10 Very Good! (1,581 reviews)
Very nice and clean great staff

Reviewed on Mar 1, 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 ₩152,320 per night from Mar 22 to Mar 23
₩152,320
₩177,263 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (1,072 reviews)
Everyone was nice. The room was bigger than expected. The room wasn’t warm enough and would blow cold air instead of hot. I didn’t complain or ask for another room because I was honestly too exhausted to complain or move. Outside of that it was lovely and we would stay again. Maybe just not in the ...

Reviewed on Mar 1, 2026

DoubleTree by Hilton Hotel Nanuet
See all 1,326 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.