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.
Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.8/10 Good! (1,511 reviews)
Great staff clean rooms soon. Guacamole was one of the best I had in a long time.

Reviewed on Aug. 7, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 23 - Oct 26
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Loved everything about it

Reviewed on Aug. 6, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (2,737 reviews)
Great place to stay and very convenient location.

Reviewed on Aug. 7, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (2,085 reviews)
I enjoyed my short stay at this hotel. It has a modern, boutique feel to it and the staff were friendly and helpful. Our double room was clean and the space was sufficient for 2 people. We did not receive the free bottle of wine that was supposed to come with VIP access.

Reviewed on Aug. 8, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.8/10 Exceptional! (1,271 reviews)
Amazing stay! Room was spotless and had everything I needed. I even forgot my phone adapter and reception was kind enough to lend me one. I would definitely recommend NobleDEN

Reviewed on Aug. 5, 2025

Ready to book your vacation to Ossining?

 

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Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

2 out of 5
1 Old Albany Post Rd, Ossining, NY
Fully refundableReserve now, pay when you stay
The price is CA $262 per night from Aug 10 to Aug 11
CA $262
CA $291 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (7 reviews)
"Staying the historic former GE Crottonville training center. The place is amazing. It wasn’t intended to be a hotel per se. It is way, way more than that. I think it is still looking for its footing as a hotel/corporate conference training center for public, so being able to stay here feels like ..."

Reviewed on Aug. 3, 2025

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
The price is CA $99 per night from Sep 2 to Sep 3
CA $99
CA $110 total
Sep 2 - Sep 3
includes taxes & fees
6/10 (1,983 reviews)
Nice last-minute booking
"It was your basic last minute motel booking nice enough to spend the night if you have to clean rooms despite the outside of appearance, but don’t make it your first pick restaurant closed bar closed, but on the high side pool is beautiful and open and open late."

Reviewed on Jul. 28, 2025

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 CA $203 per night from Aug 24 to Aug 25
CA $203
CA $232 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,392 reviews)
"The rooms were large & bright. Bathroom too- Had elevator. Nice breakfast area. Great value for the money no matter part of country that we choose a Baymont Hotel."

Reviewed on Aug. 4, 2025

Baymont by Wyndham White Plains - Elmsford
See all 1,211 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
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Frequently asked questions

How much does an Ossining vacation package cost?
You can snap up a vacation package to this top destination from CA $1,439 on Expedia. However, how much your vacation to Ossining costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Ossining?
The off-season is the best time to visit Ossining if you're trying to save. Another tip for getting cheap Ossining vacation packages? Avoid visiting during public holidays and any major events.
How many days is enough for Ossining?
Allow around 5 days for your Ossining vacation to really immerse yourself in everything that makes this place unique. Stroll around key areas, including Town of Clarkstown and Town of Mount Pleasant. Then make a beeline for major sights like Thomas J. Watson Research Centre and Rockwood Hall Park. With a well-planned itinerary, you can keep busy with room for some rest time too. Want to go beyond Ossining? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Ossining?
Ossining has everything you need for an unforgettable escape. Get your Ossining vacation off to a flying start by visiting popular attractions like Louis Engel Waterfront Park.
How to find the best Ossining package deals?
Start your search for an Ossining package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Ossining package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Ossining adventure off to a flying start.
Is it cheaper to book an Ossining vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Ossining vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Ossining?
Secure incredible discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Ossining break.
How to plan a trip to Ossining?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Ossining.
  2. Plan your budget wisely: Besides the price of your accommodations, you should consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that could arise during your trip to Ossining.
  3. Decide your trip length: Consider how long you want to spend exploring Ossining. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Ossining vacation package.

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