
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.

Outsite Chelsea
Manhattan
Save 100% on your flight
per person
3 Oct - 8 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (8 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.
Reviewed on 25 Jun 2025

The Knickerbocker Hotel
Manhattan
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per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,535 reviews)
Staff friendly and helpful. Especially Paola and Marcelo. Hotel is in nice location, clean and rooms are big.
Reviewed on 22 Jul 2025


Interfaith 21
Manhattan
Save 100% on your flight
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (19 reviews)
During my stay in NYC I couldn’t have stayed at a better place. Even though guests share the bathroom, it was not a big deal and the staff were very nice and helpful. I will definitely stay there again.
Reviewed on 19 Jul 2025

Arthouse Hotel New York City
Manhattan
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per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,487 reviews)
Lovely hotel in an amazing neighborhood. So convenient and quiet. Room was clean and very comfortable.
Reviewed on 3 Aug 2025
Top hotels in Ossining

Windrose On Hudson
1 Old Albany Post Rd, Ossining, NY
The price is €239 per night from 17 Aug to 18 Aug
€239
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (7 reviews)
"Very unique property. It's a big onsite property like a campus - and they have carved out a hotel area. Very new, well kept buildings and grounds. The location is actually on a long hiking trail with beautiful views. The room wasn't huge but very clean and beautiful floor to ceiling windows. Staff ..."
Reviewed on 30 Jul 2025

Armoni Inn & Suites
329 Route 303, Orangeburg, NY
The price is €69 per night from 2 Sept to 3 Sept
€69
2 Sept - 3 Sept
includes taxes & fees
6/10 (1,980 reviews)
"Good"
Reviewed on 20 Jul 2025

Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is €142 per night from 10 Aug to 11 Aug
€142
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (1,383 reviews)
Visit stay
"For me it was close to the hospital and the staff at the hotel was friendly and gave me a good suggestions for places to eat."
Reviewed on 29 Jul 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.
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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.