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 ₩255,828 per night from May 24 to May 25
₩255,828
₩284,919 total
May 24 - May 25
includes taxes & fees
8.4/10 Very Good! (137 reviews)
Staff was phenomenal and very accomodating.

Reviewed on May 11, 2026

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is ₩105,906 per night from May 17 to May 18
₩105,906
₩117,941 total
May 17 - May 18
includes taxes & fees
6/10 (2,192 reviews)
No microwave in rooms

Reviewed on May 14, 2026

Armoni Inn & Suites
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 ₩219,260 per night from May 17 to May 18
₩219,260
₩250,779 total
May 17 - May 18
includes taxes & fees
8.4/10 Very Good! (1,682 reviews)
I appreciated the clean room and the breakfast.

Reviewed on May 13, 2026

Baymont by Wyndham White Plains - Elmsford
See all 1,347 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

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

Sing Sing Prison Museum

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

Sing Sing Prison Museum

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.