Ossining Vacations from ￥326,257

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The Latest Ossining Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Park Lane New York

Park Lane New York

5 out of 5
Manhattan
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.6/10 Excellent! (1,401 reviews)
Love staying by central park!

Reviewed on Apr 9, 2025

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
per person
May 22 - May 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.8/10 Excellent! (1,007 reviews)
A great property I highly recommend getting a Central Park view room

Reviewed on Mar 31, 2025

The Gardens Sonesta ES Suites New York

The Gardens Sonesta ES Suites New York

3 out of 5
Manhattan
per person
May 14 - May 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
The staff was amazing and so accommodating! I was concerned we’d be too loud since we went for my friend’s bachelorette but there were no issues! Kryz (I hope I spelled it correctly) is so nice and funny. Was very kind and conversational when helping us with out luggage. The staff had great recommendations of local shops.

Reviewed on Apr 2, 2025

Soho Grand Hotel

Soho Grand Hotel

4.5 out of 5
Manhattan
per person
May 22 - May 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (1,097 reviews)
Great spot close to Subway, friendly staff cool bar.

Reviewed on Apr 9, 2025

Renaissance New York Times Square Hotel by Marriott

Renaissance New York Times Square Hotel by Marriott

4 out of 5
Manhattan
per person
May 22 - May 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.8/10 Excellent! (1,347 reviews)
2nd time staying at M Social & I loved it just as much as the first. Clean, modern, hip & chic. Family friendly as well. Walkable to anywhere really.

Reviewed on Apr 9, 2025

Find the Best Ossining Vacation Packages

Ossining Hotel Deals

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 ￥17,422 per night from Apr 17 to Apr 18
￥17,422
￥20,513 total
includes taxes & fees
Apr 17 - Apr 18
8/10 Very Good! (1,333 reviews)
"My daughter and I enjoyed our night day. Breakfast was pretty good. Staff and environment was excellent."

Reviewed on Apr 7, 2025

Hampton Inn & Suites Yonkers
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 ￥16,589 per night from Apr 20 to Apr 21
￥16,589
￥18,975 total
includes taxes & fees
Apr 20 - Apr 21
8.2/10 Very Good! (1,283 reviews)
Exceptional service
"The hotel experience was exceptional. The only thing i would suggest is a wider variety of breakfast food."

Reviewed on Apr 6, 2025

Baymont by Wyndham White Plains - Elmsford
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is ￥12,682 per night from Apr 17 to Apr 18
￥12,682
￥14,720 total
includes taxes & fees
Apr 17 - Apr 18
8.4/10 Very Good! (1,578 reviews)
"The staff was friendly and helpful, the hhotel is a bit outdated with decor and furniture from the 90s but this is shown on the site as well. The highway is close about 1 block away which can be great but bad with noises. But besides that not a bad place for a night."

Reviewed on Apr 6, 2025

Amsterdam Hotel
See all 1,154 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 from ￥326,257 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

Thomas J. Watson Research Center

Learn about the local history of Ossining with a stop at Thomas J. Watson Research Center. Stroll along the riverfront in this quaint area, or check out its top-notch restaurants.

Thomas J. Watson Research Center

Sing Sing Prison Museum

You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this family-friendly 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.