Ossining Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Linda Zanetti
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to ₩9,995 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Ossining Hotel Deals

Armoni Inn & Suites
Armoni Inn & Suites
3.5 out of 5
329 Route 303, Orangeburg, NY
Fully refundableReserve now, pay when you stay
The price is ₩110,172 per night from Jul 4 to Jul 5
₩110,172
per night
Jul 4 - Jul 5
6/10 (1,237 reviews)
"Very quiet"

Reviewed on Jun 13, 2024

Armoni Inn & Suites
Baymont by Wyndham White Plains - Elmsford
Baymont by Wyndham White Plains - Elmsford
2.5 out of 5
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is ₩197,358 per night from Jun 23 to Jun 24
₩197,358
per night
Jun 23 - Jun 24
8.2/10 Very Good! (1,034 reviews)
"Had a great stay! Staff is friendly and the breakfast is great!"

Reviewed on Jun 13, 2024

Baymont by Wyndham White Plains - Elmsford
Royal Regency Hotel
Royal Regency Hotel
3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is ₩386,170 per night from Jun 21 to Jun 22
₩386,170
per night
Jun 21 - Jun 22
8/10 Very Good! (1,474 reviews)
"Is a great and beautiful place ❤️"

Reviewed on Jun 12, 2024

Royal Regency Hotel
See all 1,003 properties in Ossining
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.

Frequently asked questions

How much does an Ossining vacation package cost?
Customize your Ossining package from just . Pick from any combination of flights, hotels and rental cars to create the trip of your dreams. Remember to add on one or two experiences!
How do I get a cheap travel package to Ossining?
Combine your flights and hotels, add extras such as activities, and save with an Ossining vacation package. You won’t just pick up superb discounts on your adventure — you’ll have plenty of choice within your reach too. When you book with Expedia, you can choose from more than 550 partner airlines and 1,000,000 properties all over the world. Your next grand adventure starts right here, right now!
Where should I stay in Ossining?
A trip to Ossining isn’t complete without seeing Van Cortlandt Manor, Sing Sing Correctional Facility and Croton Point Park. Spend your evenings close to these popular sights and make sightseeing a breeze.
What are the top hotels in Ossining?
Neighbor’s House - Welcome is one of Ossining’s leading hotels. Book a room here and you can slumber peacefully knowing you’re in capable hands.
How far in advance should I book my Ossining vacation?
It depends on the airline, but it’s usually possible to compare international flights on Expedia nearly a year in advance. While it’s advisable to book ahead of time, lucky customers will occasionally score a cheaper ticket just weeks before departure dates.
What does an Expedia Ossining travel package include?
It comes down to what you’re looking for. If you’re traveling by yourself, you might decide to combine flights and hotels. Taking the whole family to Ossining? A travel package including rental cars, flights and hotels might suit you better. Expedia gives you the flexibility to tailor your travel package.
What should I know before booking an Ossining travel package?
We already have low prices. However, you’ll snap up even more bargains when you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll get transparent pricing and a terrific range of choice.
Can I choose my airline with an Ossining Expedia vacation package?
Yes, and with more than 550 airlines to pick from globally, you have loads of choice. Have a look through the available options and find out which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Ossining vacation package?
Your situation can change in the blink of an eye, so yes. You may be able to cancel and rebook your Ossining vacation package for free within 24 hours of booking. For older bookings, you can still make the necessary changes, but your car rental company, hotel or airline may impose a charge. Need more information? Have a look at our Customer Service Portal. We’re here to help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Ossining

Image for Teatown Lake Reservation

Teatown Lake Reservation

Explore the great outdoors at Teatown Lake Reservation, a lovely green space in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Teatown Lake Reservation
Image for Sing Sing Correctional Facility

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.

Sing Sing Correctional Facility
Image for Thomas J. Watson Research Center

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 quaint area, or check out its top-notch restaurants.

Thomas J. Watson Research Center

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.