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 ₩267,361 per night from Mar 1 to Mar 2
₩267,361
₩297,775 total
Mar 1 - Mar 2
includes taxes & fees
8.2/10 Very Good! (109 reviews)
Staff were very pleasant.

Reviewed on Jan 26, 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 ₩177,650 per night from Feb 22 to Feb 23
₩177,650
₩203,188 total
Feb 22 - Feb 23
includes taxes & fees
8.2/10 Very Good! (1,539 reviews)
Great

Reviewed on Feb 7, 2026

Baymont by Wyndham White Plains - Elmsford
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
The price is ₩231,413 per night from Mar 9 to Mar 10
₩231,413
₩312,490 total
Mar 9 - Mar 10
includes taxes & fees
8.6/10 Excellent! (1,277 reviews)
Checks all the boxes!

Reviewed on Feb 8, 2026

Sonesta White Plains Downtown
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

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 quaint 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.