Ossining Holidays from £1,287
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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.
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Ossining Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | LaGuardia Airport (LGA) |
Population | 25,400 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Bear Mountain State Park, Franklin D. Roosevelt State Park and Paramount Hudson Valley Theatre |
Top hotels in Ossining
Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
£177
28 Sept - 29 Sept
includes taxes & fees
8.6/10 Excellent! (245 reviews)
"The room was very basic and feels like a dorm room. The bed was very firm and uncomfortable. Did not feel like a queen size. A little small for two people. Room is set up for one person so not enough towels and pillows. Be prepared for lots of noisy late night interruptions by fellow guests. Walls ..."
Reviewed on 20 Sept 2026
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
£160
27 Sept - 28 Sept
includes taxes & fees
Armoni Inn & Suites
329 Route 303 Orangeburg NY
6.2/10 (2,267 reviews)
"Nothing worked. Complete overhaul needed."
Reviewed on 7 Sept 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
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.
Photo by louann ohora
Teatown Lake Reservation
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.
Sing Sing Prison Museum
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.
Hudson Hills Golf Course
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.
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.
Ossining Historical Society
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.
Louis Engel Waterfront Park
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.
Merchants Square
9.0/10 (2 reviews)
Explore the great outdoors at Merchants Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this quaint area.
Frequently asked questions
How much does an Ossining travel package cost?
Get your credit card ready, because a trip to Ossining starts from only £1,287. 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.
What are the top hotels in Ossining?
Make a reservation at Baymont by Wyndham White Plains - Elmsford. It's one of this neighbourhood's most popular properties. Another highly rated option in Ossining is Courtyard by Marriott Yonkers Westchester County.
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. Flight-inclusive packages are ATOL protected.
