Ossining Vacations from $488

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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.

The Latest Ossining vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $927, price is now $488 per person
$488
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
The room and grounds were very good

Reviewed on Sep 30, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $1,330, price is now $730 per person
$730
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,344 reviews)
The most inconvenient location ever. Streets dirty around the hotel. The room was so tiny and awkwardly set up. That half your bathroom was next to the bed. The only thing in its own room was a toilet even the mirror hung next to the bed over the bathroom sink And housekeeping did a terrible job though the room was clean when we first walked in. I would never stay there again and I would never stay in that area.

Reviewed on Oct 6, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,456, price is now $814 per person
$814
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,985 reviews)
Beautiful clean room, staff extremely friendly and knowledgeable.

Reviewed on Oct 8, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was $3,817, price is now $2,148 per person
$2,148
per person
Dec 12 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Very environmentally sensitive. Good location.

Reviewed on Oct 4, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $1,713, price is now $996 per person
$996
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Every staff person I interacted with was friendly and helpful. Loved the views and location. Wished there was more room to walk in the living room when the pull out sofa was open.

Reviewed on Sep 28, 2025

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Discover the most popular places to visit in Ossining

Lovely spot in Westchester, NY

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.

Teatown Lake Reservation

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

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

Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road, Ossining, NY
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $230 total per night from Nov 5 to Nov 6
$230 total
Nov 5 - Nov 6
Total with taxes and fees
8.4/10 Very Good! (34 reviews)
"We were there two nights. Primary purpose was to have a private family meeting. Doug Stone recommended Cafe 56. We conducted our meeting there at 3 pm after it closed. It was the perfect setting - comfortable, lots of light and private. We enjoyed our stay there and will recommend to others. Only ..."

Reviewed on Oct 8, 2025

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Oct 12 to Oct 13
$109 total
Oct 12 - Oct 13
Total with taxes and fees
6/10 (2,056 reviews)
"Clean, cozy, great location, very quiet."

Reviewed on Oct 3, 2025

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
$127 nightly
The price is $149 total per night from Oct 26 to Oct 27
$149 total
Oct 26 - Oct 27
Total with taxes and fees
8.2/10 Very Good! (2,297 reviews)
"Affordable and a pleasant stay. Hope you like purple."

Reviewed on Oct 7, 2025

Royal Regency Hotel
See all 1,236 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.

Ossining Essential Information

Language
English
Currency
U.S dollars
Closest Airport
LaGuardia Airport (LGA)
Population
25,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Franklin D. Roosevelt State Park, Paramount Hudson Valley Theater and Rockefeller Archive Center

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Frequently asked questions

How much does an Ossining vacation package cost?
You can snap up a vacation package to this popular destination from $488 on Expedia. However, how much your vacation to Ossining costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossining?
You can typically find reduced prices and greater availability in December, January and February. Browse our cheap Ossining vacation packages and you could land some great off-season deals.
How many days is enough for Ossining?
To get the most out of your Ossining vacation, we recommend booking for 6 days. Divide your time between visiting Louis Engel Waterfront Park, Teatown Lake Reservation and other must-see attractions, on top of exploring neighborhoods like Town of Mount Pleasant and Crotonville. If you've got some spare time, include a day trip in your Ossining vacation itinerary.
Is it worth booking a vacation package to Ossining?
Ossining is a good vacation destination with attractions like Sing Sing Correctional Facility among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, an Ossining vacation promises a good time for everyone.
How to find the best Ossining package deals?
Use Expedia's handy filters to find some tempting Ossining package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Ossining package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book an Ossining vacation as a package?
You can enjoy significant savings on your Ossining retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Ossining?
If you have your Ossining travel dates locked in, book as early as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Ossining vacation packages?
If you're anything like us, you love going away but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Ossining vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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