Ossining Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,722, price is now CA $1,010 per person
CA $1,010
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,713, price is now CA $1,630 per person
CA $1,630
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

LGA AIRPORT

LGA AIRPORT

2 out of 5
Queens
Price was CA $2,247, price is now CA $1,416 per person
CA $1,416
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
10/10 Exceptional! (2 reviews)
The best airbnb Ive stayed at in New York with the best price for our family of 6. The place was so clean, amenities looked brand new. It had a homey feel to it, my kids didnt want to leave. We will definently be booking again in the future.

Reviewed on Dec 24, 2025

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,122, price is now CA $1,343 per person
CA $1,343
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,522, price is now CA $1,605 per person
CA $1,605
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The bar cafe in the lobby was amazing! Quick check in, clean property and very spacious rooms for this price point in NYC

Reviewed on Nov 13, 2026

Ready to book your vacation to Ossining?

 

Choose your dates

Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
The price is CA $216 per night from Dec 13 to Dec 14
CA $216
CA $240 total
Dec 13 - Dec 14
includes taxes & fees
Windrose On Hudson
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
The price is CA $180 per night from Nov 30 to Dec 1
CA $180
CA $211 total
Nov 30 - Dec 1
includes taxes & fees
LIV Hotel Bronx - Newly Built
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
The price is CA $267 per night from Dec 8 to Dec 9
CA $267
CA $342 total
Dec 8 - Dec 9
includes taxes & fees
Tarrytown House Estate
See all 1,224 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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Ossining attractions

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 $1,010 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.