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 ₩242,660 per night from Jan 4 to Jan 5
₩242,660
₩270,264 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8/10 Very Good! (102 reviews)
Great

Reviewed on Dec 20, 2025

Windrose On Hudson
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
The price is ₩142,959 per night from Jan 25 to Jan 26
₩142,959
₩175,556 total
Jan 25 - Jan 26, 2026
includes taxes & fees
8.2/10 Very Good! (2,433 reviews)
Clean room, great breakfast and great service.

Reviewed on Dec 22, 2025

Royal Regency Hotel
Ramada by Wyndham Bronx

Ramada by Wyndham Bronx

3 out of 5
1000 Baychester Ave Bronx NY
Fully refundableReserve now, pay when you stay
The price is ₩189,024 per night from Jan 11 to Jan 12
₩189,024
₩221,959 total
Jan 11 - Jan 12, 2026
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Good

Reviewed on Dec 20, 2025

Ramada by Wyndham Bronx
See all 1,312 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.