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 ₩275,955 per night from Mar 6 to Mar 7
₩275,955
₩307,344 total
Mar 6 - Mar 7
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 ₩195,495 per night from Mar 8 to Mar 9
₩195,495
₩223,597 total
Mar 8 - Mar 9
includes taxes & fees
8.2/10 Very Good! (1,589 reviews)
Safe, quiet, clean and predictable. If you are looking for a place to stay with no drama, comfortable beds, and easy parking then this is a really good spot! I I appreciate how easy it is to access MSK. My only advice is if you’re not feeling well make sure you don’t get a room by the vending machine ...

Reviewed on Mar 4, 2026

Baymont by Wyndham White Plains - Elmsford
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
The price is ₩171,557 per night from Mar 8 to Mar 9
₩171,557
₩202,034 total
Mar 8 - Mar 9
includes taxes & fees
7.2/10 Good! (475 reviews)
Internet was super fast, room was in a good condition, AC /Heater worked fine .

Reviewed on Mar 4, 2026

LIV Hotel Bronx - Newly Built
See all 1,333 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.