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Your Ossining Holiday
Experience the energy and excitement of Ossining with a tailor-made Ossining holiday 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 holiday to Ossining now.
Discover the most popular places to visit in Ossining
Travelers Rest
This historic former stagecoach stop serves exceptional American and German cuisine in elegant, fireplace-lit dining rooms. Stroll through the landscaped gardens with waterfalls before your memorable meal.
This 1,000-acre nature preserve features diverse ecosystems along scenic trails. Explore the floating boardwalk across the lake for wildlife viewing and see the island's native wildflower collection.
Step inside America's most infamous prison at the Sing Sing Prison Museum, opening in 2025 for its 200th anniversary. Explore artefacts and stories illuminating incarceration and rehabilitation in America.
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.
Louis Engel Waterfront Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
This intimate museum preserves Ossining's heritage through artefacts connected to Sing Sing Prison and local history. Schedule a personalised appointment for the most enriching exploration of this community treasure.
Nestled in Ossining's rolling terrain, this Mark Mungeam-designed course challenges players with strategic bunkers and undulating fairways. Enjoy Hudson River Valley views while navigating the thoughtful 18 holes.
Nelson Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this quaint area or visit its top-notch restaurants.
"Second stay. Furniture etc a little worn since last stay, which was shortly after it opened.
Everything was clean. Bed comfortable. We did not eat in the restaurant. Would stay again."
"The price & location were good, approx 10 mins outside of Sleepy Hollow where we were visiting. I have stayed at many HI Express’s and the front desk staff here was the least friendly of any I have stayed at. A simple Hello or Have a good night goes a long way. The staff in the breakfast buffet were very friendly. Our room was clean but in a very odd location-it was the first room outside the lobby. It was noisy in the morning when people were having their breakfast. I would not recommend this...
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.
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.
Get your credit card ready, because a trip to Ossining starts from only £1,799. When you bundle your hotels, flights and car rentals into a travel package, you'll land the biggest bargains.
If I'm not able to travel, can I cancel my Ossining travel package?
Yes, you can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Ossining travel package. You may be able to cancel or change your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Ossining?
Booking a flight and hotel together with Expedia won't just save precious time — it'll save you cash too. An Ossining travel package makes it a breeze to create the ideal trip. With more than 550 airlines throughout the world to pick from, finding convenient flights that suit your busy schedule won't be a challenge. Not only that, we've got over 1,000,000 properties globally to choose from. Talk about choice! No matter who you are, Expedia puts the world within your reach.
Does Expedia offer Book Now, Pay Later Ossining holidays?
Good news! We do. Expedia has partnered with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your trip. Be sure to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:
Pay monthly holidays: If paying bite-sized amounts each month works for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams come true.
Pay in instalments holidays: If you'd like to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan from Klarna.
Where should I stay in Ossining?
You'll want to stay where the action is. Many travellers favor hotels in the vicinity of popular sights, such as Van Cortlandt Manor, Thomas J. Watson Research Centre and Sing Sing Correctional Facility.
How far in advance should I book my Ossining holiday?
It all depends on the air carrier, but you can generally compare international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers occasionally score a cheaper seat only weeks before the date of departure.
What does an Expedia Ossining travel package include?
Rental cars, flights and hotels, or any combination of the three — it's your pick! Whether you're headed to Ossining with the entire family or travelling solo, there's a package to fit your style and budget. Once you've made your booking, why not add on some tours and experiences?
What should I know before booking an Ossining travel package?
When you book your hotels, flights and car rentals together, you'll enjoy great discounts. Whether you're organising an island getaway in a villa or want to stay in a cosy apartment in the city, Expedia can help make it happen.
Can I choose my airline with an Ossining Expedia travel package?
You can, and with more than 550 airlines to select from around the world, you have plenty of choice. Take a look at the available options and see which airline suits your needs and budget.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.