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.
Loews Regency New York Hotel
Manhattan
Save 100% on your flight
Price was €2,266, price is now €1,385 per person
€1,385
per person
19 Jan - 24 Jan
found 22 hours ago
Return flight included
Dublin (DUB) to New York (NYC)
9/10 Wonderful! (1,002 reviews)
helpful staff, nice rooms, location
Reviewed on 24 Nov 2025
The Fifth Avenue Hotel
Manhattan
Save 100% on your flight
Price was €2,747, price is now €1,581 per person
€1,581
per person
19 Jan - 24 Jan
found 22 hours ago
Return flight included
Dublin (DUB) to New York (NYC)
9.6/10 Exceptional! (159 reviews)
What an incredibly beautiful place this hotel is! Staff cannot do enough and made ourspecial anniversary stay truly perfect..the hotel is beautifully decorated and immaculate throughout.
Cannot recommend this enough
Reviewed on 17 Nov 2025
1 Hotel Central Park
Manhattan
Save 100% on your flight
Price was €2,459, price is now €1,504 per person
€1,504
per person
19 Jan - 24 Jan
found 22 hours ago
Return flight included
Dublin (DUB) to New York (NYC)
9/10 Wonderful! (1,001 reviews)
Small hotel with small rooms, but the decor was very nice.
Reviewed on 28 Nov 2025
The Langham, New York, Fifth Avenue
Manhattan
Save 100% on your flight
Price was €2,434, price is now €1,600 per person
€1,600
per person
19 Jan - 24 Jan
found 22 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.4/10 Exceptional! (1,001 reviews)
Clean spacious room. Courteous staff. Noise issue quickly resolved to our satisfaction.
Reviewed on 24 Nov 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 €147 per night from 1 Dec to 2 Dec
€147
1 Dec - 2 Dec
includes taxes & fees
7.8/10 Good! (89 reviews)
Clean large room.
Reviewed on 23 Nov 2025
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
The price is €125 per night from 30 Nov to 1 Dec
€125
30 Nov - 1 Dec
includes taxes & fees
8.2/10 Very Good! (1,466 reviews)
Good facilities, clean large room, friendly helpful staff
Reviewed on 26 Nov 2025
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
The price is €109 per night from 1 Dec to 2 Dec
€109
1 Dec - 2 Dec
includes taxes & fees
8.2/10 Very Good! (2,395 reviews)
it was great
Reviewed on 26 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
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 family-friendly 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 quaint area's riverfront and enjoy its top-notch restaurants.
Nelson Park
Nelson Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this quaint area or visit 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.
