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.
Hampton Inn Madison Square Garden Area Hotel

Hampton Inn Madison Square Garden Area Hotel

3 out of 5
Manhattan
Price was CA $1,290, price is now CA $859 per person
CA $859
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.2/10 Very good! (1,515 reviews)
The hotel was good overall and budget friendly. However, limited options for breakfast especially for vegetarians.

Reviewed on Jul 10, 2026

5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Manhattan
Price was CA $7,559, price is now CA $4,508 per person
CA $4,508
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.4/10 Very good! (5 reviews)

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was CA $1,528, price is now CA $955 per person
CA $955
per person
Sep 11 - Sep 14
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very good! (1,710 reviews)
They don't have enough air-conditioning. The room was HOT and not in a good way.

Reviewed on Jul 12, 2026

Pestana CR7 Times Square

Pestana CR7 Times Square

4 out of 5
Manhattan
Price was CA $1,784, price is now CA $1,123 per person
CA $1,123
per person
Aug 19 - Aug 25
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,011 reviews)
Nice hotel

Reviewed on Jul 11, 2026

Hotel AKA NoMad

Hotel AKA NoMad

4 out of 5
Manhattan
Price was CA $1,521, price is now CA $1,016 per person
CA $1,016
per person
Oct 2 - Oct 5
found 18 hours ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
.

Reviewed on Jul 6, 2026

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Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
The price is CA $292 per night from Jul 14 to Jul 15
CA $292
CA $325 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (187 reviews)
"Beautiful location and good property for YOUNG, ATHLETIC folks able to navigate the hills and distances between venues. Not so good for those with disabilities or just tired old knees, hips and hearts! Doors very heavy and w/o automated openers, shower floors very slippery, only two USB outlets in ..."

Reviewed on Jul 8, 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 $118 per night from Jul 23 to Jul 24
CA $118
CA $131 total
Jul 23 - Jul 24
includes taxes & fees
6/10 (2,292 reviews)
"Smelly rooms- had humidity smell throughout. Not clean towels"

Reviewed on Jul 12, 2026

Armoni Inn & Suites
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
The price is CA $263 per night from Jul 16 to Jul 17
CA $263
CA $348 total
Jul 16 - Jul 17
includes taxes & fees
8.8/10 Excellent! (1,329 reviews)
"Staff at the dining area are sweet and nice. The younger white man who booked my room, helped me to get Uber to the convention hall was fine. Two middle aged Latina women, ( day time) are unhelpful, stupid, and unfriendly. They also don't understand English. Should be replaced or moved to other jobs. ..."

Reviewed on Jul 11, 2026

Sonesta White Plains Downtown
See all 1,327 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 $859 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.