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.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 12 - Jul. 15
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
Great location! Great service!

Reviewed on May 20, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 19 - Aug. 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New York (JFK)
9.2/10 Wonderful! (545 reviews)
the incredible location I had a wonderful experience, want to come back

Reviewed on May 28, 2024

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Jul. 12 - Jul. 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,004 reviews)
This place is perfect

Reviewed on Jun. 4, 2024

The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
Aug. 30 - Sep. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,005 reviews)
Staff amazing! Concierge amazing Daniella is always fantastic with customer service!

Reviewed on Jun. 4, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 8 - Aug. 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,007 reviews)
The location was perfect. Nearby sights, restaurants, and easy access to transportation. The Hotel was beautiful and service was great!

Reviewed on Jun. 4, 2024

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 CA $103 per night from Jun. 19 to Jun. 20
CA $103
CA $115 total
includes taxes & fees
Jun 19 - Jun 20
6/10 (1,193 reviews)
Great
"There was a very load noise coming from the bathroom pipes almost like jack hammering"

Reviewed on Jun. 3, 2024

Armoni Inn & Suites
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 CA $225 per night from Jun. 13 to Jun. 14
CA $225
CA $284 total
includes taxes & fees
Jun 13 - Jun 14
8/10 Very Good! (1,508 reviews)
"We were very impressed with this property as we needed a place to stay for one night. Our room was beautiful and very clean. Our one sticking point is that there is a restaurant under the hotel. The restaurant has live music on the weekends and the music was so loud it came up through our room on ..."

Reviewed on Jun. 3, 2024

Royal Regency Hotel
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Jun. 6 to Jun. 7
CA $136
CA $158 total
includes taxes & fees
Jun 6 - Jun 7
8.4/10 Very Good! (1,508 reviews)
SATISFIED REPEAT CUSTOMER.
"THIS IS MY GO TO HOTEL WHEN I WORK IN THE AREA WHICH IS ABOUT 7 0R 8 TIMES A YEAR. I HAVE BEEN USING THIS HOTEL ABOUT 10 YEARS AND LIKE IT VERY MUCH. IT IS CLEAN, QUIET& COMFORTABLE. THE DESK STAFF KNOWS ME SOMEWHAT SO IT'S NICE WHEN I ARRIVE TO BE ADDRESSED BY NAME. THE ENTIRE STAFF IS VERY FRIENDLY ..."

Reviewed on May 31, 2024

Amsterdam Hotel
See all 1,018 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

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Frequently asked questions

How much does an Ossining vacation package cost?
Customize your Ossining package from just CA $980. 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 quaint 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

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