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 ₩267,999 per night from Mar 4 to Mar 5
₩267,999
₩298,484 total
Mar 4 - Mar 5
includes taxes & fees
8.2/10 Very Good! (112 reviews)
We loved it

Reviewed on Feb 16, 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 ₩182,986 per night from Feb 25 to Feb 26
₩182,986
₩209,290 total
Feb 25 - Feb 26
includes taxes & fees
8.2/10 Very Good! (1,566 reviews)
Clean, comfortable bed and great breakfast!!

Reviewed on Feb 18, 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
Fully refundableReserve now, pay when you stay
The price is ₩245,826 per night from Mar 1 to Mar 2
₩245,826
₩329,370 total
Mar 1 - Mar 2
includes taxes & fees
8.8/10 Excellent! (1,304 reviews)
The pros: our room was lovely with a large bathroom and great lighting, with very comfortable beds and plenty of pillows. Everything was very clean, too. We needed a few things sent up during our stay [extra water bottles, a bandaid] and the staff was VERY helpful and quick- upon checking in the ...

Reviewed on Feb 18, 2026

Sonesta White Plains Downtown
See all 1,323 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.