Ossining Holidays
Photo by Linda Zanetti
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Top Flight + Hotel Deals in Ossining
Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Times Square
Manhattan
Save 100% on your flight
Price was €1,660, price is now €1,089 per person
€1,089
per person
23 Dec - 28 Dec
found 6 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,957 reviews)
La habitación un poco pequeña pero limpia lo único que el hotel es muy caro para lo que esperamos cuando llegamos y el elevador realmente da miedo porque suena mucho y va demasiado rápido piensas que te vas a cer de ahí en fuera no fue tal mal y estaba muy céntrico de todo
Reviewed on 13 Oct 2025
NobleDEN Hotel
Manhattan
Price was €2,678, price is now €1,616 per person
€1,616
per person
20 Nov - 24 Nov
found 7 hours ago
Return direct flight included
Warsaw (WAW) to New York (JFK)
9.8/10 Exceptional! (1,344 reviews)
This is my go to hotel! Do yourself a favor and get the balcony room!
Reviewed on 13 Oct 2025
Omni Berkshire Place
Manhattan
Save 100% on your flight
Price was €2,077, price is now €1,283 per person
€1,283
per person
23 Dec - 28 Dec
found 6 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (1,985 reviews)
The staff go out of their way to make you feel at home
Reviewed on 11 Oct 2025
Hotel 32 32
Manhattan
Save 100% on your flight
Price was €1,706, price is now €1,146 per person
€1,146
per person
23 Dec - 28 Dec
found 6 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8/10 Very Good! (2,177 reviews)
being in the room itself is very relaxing, could fix a few things maintenance wise but overall a great stay.
Reviewed on 14 Oct 2025
Top hotels in Ossining
Windrose On Hudson
1 Shady Lane Farm Road, Ossining, NY
Fully refundableReserve now, pay when you stay
The price is €198 per night from 5 Nov to 6 Nov
€198
5 Nov - 6 Nov
includes taxes & fees
8.4/10 Very Good! (34 reviews)
"We were there two nights. Primary purpose was to have a private family meeting. Doug Stone recommended Cafe 56. We conducted our meeting there at 3 pm after it closed. It was the perfect setting - comfortable, lots of light and private. We enjoyed our stay there and will recommend to others. Only ..."
Reviewed on 8 Oct 2025
Armoni Inn & Suites
329 Route 303, Orangeburg, NY
Fully refundableReserve now, pay when you stay
6/10 (2,105 reviews)
Nice hotel with big rooms
"We're staying in the hotel for one night with our friends. We're going to say that it is long time we didn't see so good hotel for so low price. Recommended."
Reviewed on 12 Oct 2025
Royal Regency Hotel
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is €137 per night from 26 Oct to 27 Oct
€137
26 Oct - 27 Oct
includes taxes & fees
8.2/10 Very Good! (2,303 reviews)
"I thought everything was great but in the evening it was so loud noisy and loud I thought it was supposed to be from like 10:00 p.m. till like 8:00 a.m. is supposed to be quiet but I don't know what was going on on the second floor but it was crazy yelling and screaming and I couldn't sleep at all ..."
Reviewed on 8 Oct 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
Sing Sing Correctional Facility
After visiting Sing Sing Correctional Facility, make a plan to see the other sights and activities in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
Sing Sing Prison Museum
You can spend time studying the exhibits at Sing Sing Prison Museum in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
Hudson Hills Golf Course
Enjoy a round of golf in Ossining at Hudson Hills Golf Course. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
