Ossining Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Linda Zanetti
Top hotels in Ossining
Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
The price is 3.856.761 ₫ per night from 30 Nov to 1 Dec
3.856.761 ₫
4.295.425 ₫ total
30 Nov - 1 Dec
includes taxes & fees
7.8/10 Good! (87 reviews)
Amazing facility, very beautiful and clean, well kept! The staff was kind and helpful, and the views from the room were great. Perfect place for large parties or just a weekend getaway. Highly recommend!
Reviewed on 18 Nov 2025
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
The price is 3.870.079 ₫ per night from 18 Dec to 19 Dec
3.870.079 ₫
5.300.831 ₫ total
18 Dec - 19 Dec
includes taxes & fees
8.6/10 Excellent! (1,122 reviews)
Lovely property, extremely attentive staff, with a shout out to the gentleman driving the courtesy van! A flawless (albeit too brief) stay.
Reviewed on 12 Nov 2025
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
The price is 2.728.467 ₫ per night from 1 Dec to 2 Dec
2.728.467 ₫
3.344.579 ₫ total
1 Dec - 2 Dec
includes taxes & fees
8.2/10 Very Good! (2,386 reviews)
Love it
Reviewed on 22 Nov 2025
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.
Popular places to visit
Teatown Lake Reservation
Explore the great outdoors at Teatown Lake Reservation, a lovely green space in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
Thomas J. Watson Research Center
Learn about the local history of Ossining when you take a trip to Thomas J. Watson Research Center. Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants.
Travelers Rest
After visiting Travelers Rest, make a plan to see the other sights and activities in Ossining. Amble around the area's parks or visit its monuments.
