
Ossining Vacation Packages
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Your Ossining Vacation
Experience the energy and excitement of Ossining with a tailor-made Ossining vacation package. From its rich history to its spectacular views and beyond, you'll never have a boring moment in this city. Eager to explore your surroundings? Tarrytown Music Hall, Van Cortlandt Manor and Sing Sing Correctional Facility are some of the leading places to visit during a trip to Ossining. Browse Expedia's extensive range of travel options and begin planning your perfect vacation to Ossining now.
Top Ossining Vacation Deals
Price found within the past 48 hours. Click for updated prices.




INNSiDE by Meliá New York Nomad
Manhattan
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (2,085 reviews)
I enjoyed my short stay at this hotel. It has a modern, boutique feel to it and the staff were friendly and helpful. Our double room was clean and the space was sufficient for 2 people. We did not receive the free bottle of wine that was supposed to come with VIP access.
Reviewed on Aug. 8, 2025

NobleDEN Hotel
Manhattan
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.8/10 Exceptional! (1,271 reviews)
Amazing stay! Room was spotless and had everything I needed. I even forgot my phone adapter and reception was kind enough to lend me one. I would definitely recommend NobleDEN
Reviewed on Aug. 5, 2025
Ossining Hotel Deals

Windrose On Hudson
1 Old Albany Post Rd, Ossining, NY
Fully refundableReserve now, pay when you stay
The price is CA $262 per night from Aug 10 to Aug 11
CA $262
CA $292 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (7 reviews)
"Staying the historic former GE Crottonville training center. The place is amazing. It wasn’t intended to be a hotel per se. It is way, way more than that. I think it is still looking for its footing as a hotel/corporate conference training center for public, so being able to stay here feels like ..."
Reviewed on Aug. 3, 2025

Armoni Inn & Suites
329 Route 303, Orangeburg, NY
The price is CA $99 per night from Sep 8 to Sep 9
CA $99
CA $110 total
Sep 8 - Sep 9
includes taxes & fees
6/10 (1,983 reviews)
Nice last-minute booking
"It was your basic last minute motel booking nice enough to spend the night if you have to clean rooms despite the outside of appearance, but don’t make it your first pick restaurant closed bar closed, but on the high side pool is beautiful and open and open late."
Reviewed on Jul. 28, 2025

Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Aug 17 to Aug 18
CA $198
CA $226 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (1,392 reviews)
"The rooms were large & bright. Bathroom too- Had elevator. Nice breakfast area. Great value for the money no matter part of country that we choose a Baymont Hotel."
Reviewed on Aug. 4, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.