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
The price is ₩260,916 per night from May 11 to May 12
₩260,916
₩290,596 total
May 11 - May 12
includes taxes & fees
8.4/10 Very Good! (133 reviews)
Phone in room did not work. One extra pillow granted would have liked still another. Beautiful facility and grounds very very tasteful throughout.

Reviewed on May 1, 2026

Windrose On Hudson
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
The price is ₩221,469 per night from May 20 to May 21
₩221,469
₩289,695 total
May 20 - May 21
includes taxes & fees
8.2/10 Very Good! (1,066 reviews)
Access to our room was difficult. There was a paved path from the parking lot to exterior wooden steps up to the outside door. It took several tries to get the keycard reader to work. Once inside, there was another flight of stairs to get to our floor. When we got to our room, the card key did not ...

Reviewed on May 7, 2026

Tarrytown House Estate
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
The price is ₩290,833 per night from May 21 to May 22
₩290,833
₩381,117 total
May 21 - May 22
includes taxes & fees
8.8/10 Excellent! (1,315 reviews)
Lobby restaurant was great

Reviewed on May 8, 2026

Sonesta White Plains Downtown
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

Kitchawan Preserve

Explore the great outdoors at Kitchawan Preserve, a lovely green space in Ossining. Amble around this quaint 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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