Ossining Vacations from ₩1,539,926

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The Latest Ossining Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ₩2,417,496, price is now ₩1,539,926 per person
₩1,539,926
per person
Jun 25 - Jun 27
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,411 reviews)
I was placed in a handicap accessible room, which I wasn't aware of nor was I told until I checked in to the room. the water pressure in the shower was abysmal and the TV turned on by itself in the morning. also the curtain rod to close the darkening curtains broke, so it was bright from the midtown / Times Square lights all night.

Reviewed on Apr 7, 2026

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Save 100% on your flight
Price was ₩4,598,238, price is now ₩2,443,264 per person
₩2,443,264
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,003 reviews)
The staff was very friendly and the amenities were fantastic.

Reviewed on Mar 30, 2026

Staypineapple, An Artful Hotel, Midtown

Staypineapple, An Artful Hotel, Midtown

3 out of 5
Manhattan
Save 100% on your flight
Price was ₩3,825,006, price is now ₩2,598,100 per person
₩2,598,100
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (1,217 reviews)
The Hotel was beautifully decorated. The staff were extremely kind attentive. Only down fall was the Hot water was broken that weekend.

Reviewed on Apr 6, 2026

Westgate New York Grand Central

Westgate New York Grand Central

4 out of 5
Manhattan
Save 100% on your flight
Price was ₩3,662,090, price is now ₩2,521,663 per person
₩2,521,663
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,172 reviews)
Amazing staff. Rooms are runned down

Reviewed on Apr 7, 2026

The Algonquin Hotel Times Square, Autograph Collection

The Algonquin Hotel Times Square, Autograph Collection

4 out of 5
Manhattan
Save 100% on your flight
Price was ₩3,530,274, price is now ₩2,595,949 per person
₩2,595,949
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,000 reviews)
Great location Friendly staff A sense of nyc in times gone by

Reviewed on Feb 7, 2026

Find the Best Ossining Vacation Packages

Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
The price is ₩248,721 per night from May 3 to May 4
₩248,721
₩277,036 total
May 3 - May 4
includes taxes & fees
8.2/10 Very Good! (122 reviews)
We decided stay at this hotel, because it is only option was. In general all good. Big parking lot, polite staff. But, room doesn't have fridge, and for my request slippers, they said, they don't have it. There are the reasons why I little bit disappointed.

Reviewed on Apr 5, 2026

Windrose On Hudson
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 ₩190,241 per night from Apr 15 to Apr 16
₩190,241
₩217,586 total
Apr 15 - Apr 16
includes taxes & fees
8.2/10 Very Good! (1,636 reviews)
Not a good experience

Reviewed on Apr 7, 2026

Baymont by Wyndham White Plains - Elmsford
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
The price is ₩187,913 per night from Apr 9 to Apr 10
₩187,913
₩220,887 total
Apr 9 - Apr 10
includes taxes & fees
7.4/10 Good! (557 reviews)
Check in and check out is easy.

Reviewed on Apr 7, 2026

LIV Hotel Bronx - Newly Built
See all 1,340 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 family-friendly 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

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

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