Ossining Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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.
Luxury 3BR Family Home Game Room Parking
Bryn Mawr
Price was CA $4,709, price is now CA $2,668 per person
CA $2,668
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9/10 Wonderful! (2 reviews)
Beautiful layout. Property had everything that was needed for an awesome stay.
Reviewed on Feb 27, 2026
The Towers at Lotte New York Palace
Manhattan
Price was CA $3,614, price is now CA $2,075 per person
CA $2,075
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (659 reviews)
Great location. Great views in the Towers.
Reviewed on Mar 17, 2026
WestHouse New York
Manhattan
Price was CA $2,956, price is now CA $1,779 per person
CA $1,779
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,003 reviews)
Great staff, amazing lunch and breakfast
Reviewed on Apr 9, 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 May 3 to May 4
CA $228
CA $254 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (123 reviews)
We decided stay at this hotel, because it is only option was. In general all good. Big parking lot, polite staff. But, room doesn't have fridge, and for my request slippers, they said, they don't have it. There are the reasons why I little bit disappointed.
Reviewed on Apr 5, 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 $179 per night from Apr 12 to Apr 13
CA $179
CA $205 total
Apr 12 - Apr 13
includes taxes & fees
8.2/10 Very Good! (1,644 reviews)
Bed was comfortable
Reviewed on Apr 10, 2026
LIV Hotel Bronx - Newly Built
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Apr 13 to Apr 14
CA $192
CA $225 total
Apr 13 - Apr 14
includes taxes & fees
8.2/10 Very Good! (466 reviews)
The room was disgusting. The booking said smoke free but the hallway smelled of smoke and there was an ashtray in the room. Went down to ask for a clean room and was downsized to a queen bed. The internet is horrible. I will be reaching out as this is the worse experience I’ve had via hotels.com
Reviewed on Apr 10, 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.
