Ossining Vacations from $497

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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.
Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (816 reviews)
The lobby had no AC. Makes it bad when coming in from a heatwave. Elevator very slow or didn't even come to my floor (6)

Reviewed on Jul 31, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Nice views.. but food at restaurant left a lot to be desired. Also staff presentation was terrible. They need uniforms and a dress code. Booty shorts, wrinkled clothing... its all a part of the experience and everyone looked like they got up out of bed and came to work. Take pride. Its managements fault ..

Reviewed on Jul 30, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (532 reviews)
We stayed here for an overnight for a girls trip with my 8yr old daughter, we had the best time. We will be back!

Reviewed on Jul 30, 2025

Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7/10 Good! (2,169 reviews)
staff is super nice. neighborhood is kinda loud but welcome to new york LOL. air conditioning is nice plus as well :)

Reviewed on Jul 30, 2025

Empire Hotel

Empire Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (5,628 reviews)
Pros: A nice hotel away from the crowds. Great location, comfortable room. Con: they charge a “residence fee” per night which is not included in the price they show online. I know lots of hotels in NYC are doing this, like charging “resort fees”. Such dishonest baloney. Makes it impossible to budget hotel costs.

Reviewed on Aug 1, 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 family-friendly 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

2 out of 5
1 Old Albany Post Rd, Ossining, NY
$229 nightly
The price is $255 total per night from Aug 3 to Aug 4
$255 total
Aug 3 - Aug 4
Total includes taxes and fees
7.2/10 Good! (5 reviews)
"I regret I didn’t take pictures, but the scenery was beautiful"

Reviewed on Jun 24, 2025

Windrose On Hudson
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
$148 nightly
The price is $169 total per night from Aug 24 to Aug 25
$169 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,392 reviews)
Visit stay
"For me it was close to the hospital and the staff at the hotel was friendly and gave me a good suggestions for places to eat."

Reviewed on Jul 29, 2025

Baymont by Wyndham White Plains - Elmsford
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $157 total per night from Aug 10 to Aug 11
$157 total
Aug 10 - Aug 11
Total includes taxes and fees
7.8/10 Good! (1,082 reviews)
"."

Reviewed on Jul 29, 2025

Hampton Inn White Plains/Tarrytown
See all 1,205 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.

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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 $497 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.