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 refundable
The price is 5.434.239 ₫ per night from 5 Nov to 6 Nov
5.434.239 ₫
6.052.382 ₫ total
5 Nov - 6 Nov
includes taxes & fees
8.8/10 Excellent! (22 reviews)
"The only downfall to this hotel is the walking distance you have to do from where you park then the walk uphill to the hotel. I have breathing issues,. Thank goodness they have a sitting area once you get in to rest.before going onto your room. A suggestion maybe have a valet."
Reviewed on 25 Sept 2025
Armoni Inn & Suites
329 Route 303, Orangeburg, NY
Fully refundableReserve now, pay when you stay
6/10 (2,049 reviews)
"Good I like it"
Reviewed on 29 Sept 2025
Royal Regency Hotel
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is 3.440.893 ₫ per night from 26 Oct to 27 Oct
3.440.893 ₫
4.183.487 ₫ total
26 Oct - 27 Oct
includes taxes & fees
8.2/10 Very Good! (2,311 reviews)
"It’s a very convenient hotel"
Reviewed on 30 Sept 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 quaint 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 quaint 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.
