Ossining Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 $5,423, price is now CA $2,625 per person
CA $2,625
per person
Jun 24 - Jun 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
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
Dream Hotel Bronx
South Side
Price was CA $2,007, price is now CA $1,042 per person
CA $1,042
per person
Jul 9 - Jul 14
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
7.2/10 Good! (92 reviews)
Second visit was better then the first one.
Reviewed on Apr 23, 2026
JW Marriott Essex House New York
Manhattan
Price was CA $1,698, price is now CA $1,103 per person
CA $1,103
per person
Aug 7 - Aug 10
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
Didn’t use anything from the bar. Really nice towels - thick and fluffy.
Reviewed on May 13, 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 $226 per night from May 24 to May 25
CA $226
CA $252 total
May 24 - May 25
includes taxes & fees
8.4/10 Very Good! (137 reviews)
Staff was phenomenal and very accomodating.
Reviewed on May 11, 2026
Armoni Inn & Suites
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is CA $89 per night from May 19 to May 20
CA $89
CA $99 total
May 19 - May 20
includes taxes & fees
6/10 (2,197 reviews)
Staff was good but not worth it’s too old no proper amenities or food available, hair dryer not working, it smells like burning
Reviewed on May 16, 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 $186 per night from May 31 to Jun 1
CA $186
CA $213 total
May 31 - Jun 1
includes taxes & fees
8.4/10 Very Good! (1,683 reviews)
I appreciated the clean room and the breakfast.
Reviewed on May 13, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
