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.
Seven Beach Lane
CA $1,295
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (29 reviews)
Property was extremely conveniently located to Main Street. The pool was clean with plenty of towels. Staff was pleasant. Great overall experience.
Reviewed on Aug 11, 2026
Ready to book your vacation to Ossining?
Ossining Hotel Deals
Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
CA $230
CA $256 total
Aug 20 - Aug 21
includes taxes & fees
8.6/10 Excellent! (220 reviews)
"Clean"
Reviewed on Aug 14, 2026
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
CA $221
CA $287 total
Aug 23 - Aug 24
includes taxes & fees
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
CA $152
CA $186 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (2,816 reviews)
"3rd Floor usually has a bad sewer smell ..."
Reviewed on Aug 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.
Stay near popular Ossining attractions
Travelers Rest
After visiting Travelers Rest, make a plan to see the other sights and activities in Ossining. Amble around the area's parks or visit its monuments.
Photo by louann ohora
Teatown Lake Reservation
Explore the great outdoors at Teatown Lake Reservation, a lovely green space in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
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.
Thomas J. Watson Research Center
Learn about the local history of Ossining with a stop at Thomas J. Watson Research Center. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.
Ossining Public Library
Learn about the local history of Ossining when you spend time at Ossining Public Library. Amble around the area's parks or visit its monuments.
Sing Sing Prison Museum
You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
Kitchawan Preserve
Explore the great outdoors at Kitchawan Preserve, a lovely green space in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
Depot Square
Explore the great outdoors at Depot Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this family-friendly area.
Frequently asked questions
How much does an Ossining vacation package cost?
You can snap up a vacation package to this top destination from CA $945 on Expedia. However, how much your vacation to Ossining costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Ossining?
The off-season is the best time to visit Ossining if you're trying to save. Another tip for getting cheap Ossining vacation packages? Avoid visiting during public holidays and any major events.
How many days is enough for Ossining?
Allow around 5 days for your Ossining vacation to really immerse yourself in everything that makes this place unique. Stroll around key areas, including Town of Clarkstown and Town of Mount Pleasant. Then make a beeline for major sights like Thomas J. Watson Research Centre and Rockwood Hall Park. With a well-planned itinerary, you can keep busy with room for some rest time too. Want to go beyond Ossining? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Ossining?
Ossining has everything you need for an unforgettable escape. Get your Ossining vacation off to a flying start by visiting popular attractions like Louis Engel Waterfront Park.
How to find the best Ossining package deals?
Start your search for an Ossining package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Ossining package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Ossining adventure off to a flying start.
Is it cheaper to book an Ossining vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Ossining vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Ossining?
Secure incredible discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Ossining break.
How to plan a trip to Ossining?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Ossining.
- Plan your budget wisely: Besides the price of your accommodations, you should consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that could arise during your trip to Ossining.
- Decide your trip length: Consider how long you want to spend exploring Ossining. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Ossining vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
