Ossining Vacations from ₩1,231,723
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Ossining Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel 32 32
Manhattan
Save 100% on your flight
Price was ₩1,839,695, price is now ₩1,231,723 per person
₩1,231,723
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
8/10 Very Good! (2,397 reviews)
Clean and convenient
Reviewed on May 2, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
Save 100% on your flight
Price was ₩2,567,351, price is now ₩1,359,102 per person
₩1,359,102
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,468 reviews)
The room was spacious and clean with comfortable bed. Check-in and check-out was fast and easy. The location is short walk to Times Square and Theater District which was important because transportation is really expensive. I enjoyed my stay.
Reviewed on May 3, 2026
Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
Price was ₩2,370,854, price is now ₩1,276,930 per person
₩1,276,930
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,979 reviews)
Excellent position. Very clean. Very good breakfast. Would recommend.
Reviewed on Apr 30, 2026
OYO Times Square
Manhattan
Save 100% on your flight
Price was ₩1,913,562, price is now ₩1,272,238 per person
₩1,272,238
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
7/10 Good! (1,855 reviews)
Great location if you want to be near Times Square. Rooms are good size with basic amenities but no refrigerator. The bed is not sturdy, creaks when you move. If you just need a place to stay near Broadway and TimeSquare this is a great alternative.
Reviewed on May 2, 2026
Find the Best Ossining Vacation Packages
Ossining Hotel Deals
Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
The price is ₩242,595 per night from May 24 to May 25
₩242,595
₩270,212 total
May 24 - May 25
includes taxes & fees
8.4/10 Very Good! (133 reviews)
Phone in room did not work. One extra pillow granted would have liked still another. Beautiful facility and grounds very very tasteful throughout.
Reviewed on May 1, 2026
Armoni Inn & Suites
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is ₩104,612 per night from May 5 to May 6
₩104,612
₩116,500 total
May 5 - May 6
includes taxes & fees
6/10 (2,193 reviews)
Not bad… you get what you pay for….we slept we washed.
Reviewed on May 3, 2026
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
The price is ₩172,147 per night from May 10 to May 11
₩172,147
₩210,061 total
May 10 - May 11
includes taxes & fees
8.4/10 Very Good! (2,610 reviews)
Always clean, great service and amazing breakfast!
Reviewed on May 4, 2026
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.
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.
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.
Explore a world of travel with Expedia
- Budget Rental Cars in John F. Kennedy Intl.
- Rental cars John F. Kennedy Intl. airport
- Car rentals near Taipei Gallery and Theater
- Car rentals near Town of Washington
- Car rentals near NYC-All Airports
- Car rentals near New York County
- Car rentals near Flushing Chinatown
- Car rentals near LIFE The Place To Be
- Car rentals near New York
- Alamo Rent A Car Rental Cars in John F. Kennedy Intl.
- Car rentals near Koreatown
- Car rentals near Central Park South
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
