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.
2 bedroom luxury Empire State VIEW
Manhattan
Price was CA $5,745, price is now CA $2,879 per person
CA $2,879
per person
Jul 12 - Jul 15
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!
Reviewed on Mar 19, 2026
Ossining Hotel Deals
Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
The price is CA $228 per night from Jun 21 to Jun 22
CA $228
CA $254 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (156 reviews)
"Absolutely loved this property…. so peaceful and beautiful and inviting. Every day we found a new nook or cranny to sit and relax. The coffee bar off the lobby was a nice surprise. Would have been even nicer if there been a mini fridge in the room but looking forward to returning again in the near ..."
Reviewed on May 26, 2026
Armoni Inn & Suites
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from May 28 to May 29
CA $98
CA $109 total
May 28 - May 29
includes taxes & fees
6/10 (2,210 reviews)
"Room wasn’t clean and furniture dirty bathroom was very dirty I took pics of the door and the sink I was so tired I couldn’t go back the the front desk"
Reviewed on May 25, 2026
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Jun 10 to Jun 11
CA $178
CA $204 total
Jun 10 - Jun 11
includes taxes & fees
8.4/10 Very Good! (1,705 reviews)
"My stay was pleasant the breakfast was a bonus very clean and well stocked. The room was very nice and clean . The pool was a plus also thank you"
Reviewed on May 26, 2026
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.
