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.
Kixby

Kixby

4 out of 5
Manhattan
Price was CA $2,290, price is now CA $1,490 per person
CA $1,490
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,933 reviews)
Held a private event with music blaring and bass till 11:30pm. Room right above it. Their team legitimately didn’t care because they booked for a private event. People book hotels to sleep - I had to be up and working an event at 6:30 the next day. To allow music till that time is greedy- get a decent music ending time in order and respect your guests.

Reviewed on Jun 30, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,180, price is now CA $2,473 per person
CA $2,473
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Nicely designed hotel with beautiful views. Staff was very nice but service was generally slow.

Reviewed on Jun 28, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $3,412, price is now CA $2,209 per person
CA $2,209
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,632 reviews)
Room was excellent, hotel was lovely and location was perfect for exploring the city. Especially enjoyed happy hour in the lounge.

Reviewed on Jun 30, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $3,530, price is now CA $2,287 per person
CA $2,287
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,099 reviews)
Excellent service snd breakfast

Reviewed on Jun 30, 2026

The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Price was CA $2,681, price is now CA $1,792 per person
CA $1,792
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (695 reviews)
Amazing! Loved my stay there. The hotel was a 10/10.

Reviewed on Jun 29, 2026

Ready to book your vacation to Ossining?

 

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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
The price is CA $280 per night from Jul 1 to Jul 2
CA $280
CA $312 total
Jul 1 - Jul 2
includes taxes & fees
8.6/10 Excellent! (177 reviews)
"GREAT STAFF GREAT LOCATION GREAT ROOMS, OVERALL GREAT EXPERIENCE"

Reviewed on Jun 30, 2026

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
The price is CA $121 per night from Jul 20 to Jul 21
CA $121
CA $135 total
Jul 20 - Jul 21
includes taxes & fees
6/10 (2,270 reviews)
"Hay muchas cosas que no están en functionamiento como la pisina el gym y la labanderia no estaban funcionando yo ise una reservation por 4 días y lo ise porque decia que tenía picsina y por mis niños que queria bañarse hay lo hise"

Reviewed on Jun 29, 2026

Armoni Inn & Suites
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
The price is CA $171 per night from Jul 6 to Jul 7
CA $171
CA $196 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very good! (1,534 reviews)
"Clean room"

Reviewed on Jun 30, 2026

Hampton Inn White Plains/Tarrytown
See all 1,340 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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Stay near popular Ossining attractions

A dam with a reservoir, surrounded by autumn foliage and hills.

Travelers Rest

After visiting Travelers Rest, make a plan to see the other sights and activities in Ossining. Amble around the area's parks or visit its monuments.
See properties

Frequently asked questions

How much does an Ossining vacation package cost?
You can snap up a vacation package to this top destination from CA $1,490 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.

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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.