Ossining Vacations

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Find the Best Ossining Vacation Packages

Ossining Hotel Deals

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 NT$1,765 per night from Mar 22 to Mar 23
NT$1,765
NT$1,965 total
includes taxes & fees
Mar 22 - Mar 23
6/10 (1,861 reviews)
"👍"

Reviewed on 2025/2/21

Armoni Inn & Suites
Royal Regency Hotel
Royal Regency Hotel
3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is NT$3,027 per night from Mar 9 to Mar 10
NT$3,027
NT$4,186 total
includes taxes & fees
Mar 9 - Mar 10
8.2/10 Very Good! (1,999 reviews)
"Check in staff were wonderful and pleasant. Very good details about how parking, food, property etc."

Reviewed on 2025/2/22

Royal Regency Hotel
Hampton Inn & Suites Yonkers
Hampton Inn & Suites Yonkers
2.5 out of 5
160 Corporate Blvd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is NT$3,313 per night from Feb 27 to Feb 28
NT$3,313
NT$3,901 total
includes taxes & fees
Feb 27 - Feb 28
8/10 Very Good! (1,199 reviews)
"Property looks amazing and so do the rooms. The staff is very professional and welcoming. Highly recommend!!!"

Reviewed on 2025/2/19

Hampton Inn & Suites Yonkers
See all 1,106 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.

Frequently asked questions

How much does an Ossining vacation package cost?
You can snap up a vacation package to this popular destination 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?
The off-season is the best time to head to Ossining if you’re hoping to keep costs down. Another tip for scoring cheap Ossining vacation packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Ossining?
To fully enjoy your Ossining vacation, we recommend staying for 5 days. Divide your time between visiting Teatown Lake Reservation, Kitchawan Preserve and other top attractions, in addition to experiencing neighborhoods like Town of Mount Pleasant and Pleasantville. If you’ve got some time to spare, add a tour or day trip to your Ossining vacation itinerary.
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 top attractions like Louis Engel Waterfront Park.
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.
How to plan a trip to Ossining?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Ossining.
  2. Budget wisely: Besides the price of your accommodations, you’ll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Ossining.
  3. Set the duration of your trip: Start by listing all the attractions and activities you’d like to get to in Ossining. Then, estimate how long you’ll need at each, including any travel time.
  4. Bundle your accommodations and airfare: After you’ve settled on your dates and duration, lock in the ideal Ossining vacation package for you.

Discover the most popular places to visit in Ossining

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

Ossining Historical Society

You can spend an afternoon studying the exhibits at Ossining Historical Society during your trip to Ossining. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Ossining Historical Society

Sing Sing Prison Museum

You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

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