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 ₩249,241 per night from Jun 21 to Jun 22
₩249,241
₩277,615 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (152 reviews)
"Beautiful property"

Reviewed on May 25, 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 ₩107,478 per night from May 27 to May 28
₩107,478
₩119,692 total
May 27 - May 28
includes taxes & fees
6/10 (2,215 reviews)
"Room wasn’t clean and furniture dirty bathroom was very dirty I took pics of the door and the sink I was so tired I couldn’t go back the the front desk"

Reviewed on May 25, 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 ₩210,724 per night from Jun 2 to Jun 3
₩210,724
₩241,016 total
Jun 2 - Jun 3
includes taxes & fees
8.4/10 Very Good! (1,700 reviews)
"Nice location and very clean."

Reviewed on May 26, 2026

Baymont by Wyndham White Plains - Elmsford
See all 1,362 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

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

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

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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.