Ossining Vacations from ₩725,851

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The Latest Ossining Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip flight included
Oklahoma City (OKC) to New York (JFK)
8.8/10 Excellent! (1,653 reviews)
Close walk to Grand Central Terminal, which you may know is one of the best ways to travel NYC is the subway. Couple blocks down from a tasy $1.50 pizza spot, perfect for the late night snack after a long day of walking the city. We had the apartment style room for a family of 4 and it was very spacious. I can't review the roof top bar/ restaurant cause we always missed the hours. My only complaint is the shower, and its lack of keeping water inside the shower pan. Maybe all that is needed are linger shower curtains, otherwise dont run the water too hard so that you don't get too much water out of the shower. Other than that, this hotel fulfulles our. requirements.

Reviewed on Jul 14, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip flight included
Oklahoma City (OKC) to New York (JFK)
8.8/10 Excellent! (6,073 reviews)
Old fashioned window air conditioning was a good thing because the noise from the unit drowned out the noise of the street. Uncomfortable beds. The only thing good about the hotel is location. It is clean enough that I would stay again just because of the location. If the hotel were nicer it would not be affordable.

Reviewed on Jul 17, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip flight included
Oklahoma City (OKC) to New York (JFK)
9/10 Wonderful! (2,098 reviews)
We were immediately impressed upon first entering this hotel by the decor, the beautiful fragrance in the air and the very attentive and friendly front desk staff. Our room and balcony were well appointed and comfortable and we thoroughly enjoyed our two night stay here!

Reviewed on Jul 14, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip flight included
Oklahoma City (OKC) to New York (JFK)
9.8/10 Exceptional! (1,232 reviews)
I’ve returned from a 5 days mother/son trip to NYC with my 14 yrs old..The experience was fantastic and staying at NobleDen made it even more special…Property was clean and quiet and the area was very safe even for late night walks…we will definitely be back ..

Reviewed on Jul 14, 2025

Arlo SoHo

Arlo SoHo

4 out of 5
Manhattan
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip flight included
Oklahoma City (OKC) to New York (JFK)
8.8/10 Excellent! (1,785 reviews)
I loved the location - walk to Subway and the convenience of restaurant / dining options on site We enjoyed breakfast at restaurant and had drinks at roof top Room was clean Complimentary water cans - perfect on a hot day The staff went beyond - with a basket upon arrival and room decorated - we were celebrating our anniversary - complimentary breakfast We were able to walk to TriBeCa- where we had dinner - really loved the location

Reviewed on Jul 10, 2025

Find the Best Ossining Vacation Packages

Ossining Hotel Deals

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 ₩156,155 per night from Jul 27 to Jul 28
₩156,155
₩190,812 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (2,157 reviews)
"My stay are always wonderful the workers are awesome and welcoming will always stay here"

Reviewed on Jul 15, 2025

Royal Regency Hotel
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 ₩209,998 per night from Jul 27 to Jul 28
₩209,998
₩240,185 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,379 reviews)
"Always a pleasant and comfortable stay."

Reviewed on Jul 16, 2025

Baymont by Wyndham White Plains - Elmsford
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 ₩189,955 per night from Jul 27 to Jul 28
₩189,955
₩217,263 total
Jul 27 - Jul 28
includes taxes & fees
7.8/10 Good! (1,062 reviews)
Not the best, but acceptable.
"Check-in and out was super easy. Room initially had an odor that reduced during our stay. Bathroom not super clean. Decided not to use the shower."

Reviewed on Jul 13, 2025

Hampton Inn White Plains/Tarrytown
See all 1,202 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.

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 quaint area's riverfront and enjoy its top-notch restaurants.

Sing Sing Prison Museum

Kitchawan Preserve

Explore the great outdoors at Kitchawan Preserve, a lovely green space in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Kitchawan Preserve

Frequently asked questions

How much does an Ossining vacation package cost?
You can snap up a vacation package to this popular destination from ₩725,851 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.

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