
Ossining Vacation Packages
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Your Ossining Vacation
Experience the energy and excitement of Ossining with a tailor-made Ossining vacation package. From its rich history to its spectacular views and beyond, you'll never have a boring moment in this city. Eager to explore your surroundings? Tarrytown Music Hall, Van Cortlandt Manor and Sing Sing Correctional Facility are some of the leading places to visit during a trip to Ossining. Browse Expedia's extensive range of travel options and begin planning your perfect vacation to Ossining now.
Top Ossining Vacation Deals
Price found within the past 48 hours. Click for updated prices.

The Inn At Fox Hollow Hotel
Price was CA $882, price is now CA $560 per person
CA $560
per person
Oct 7 - Oct 9
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful
Reviewed on Aug. 12, 2025

1 Hotel Brooklyn Bridge
Price was CA $6,783, price is now CA $3,371 per person
CA $3,371
per person
Nov 9 - Nov 16
found 23 hours ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Rooms are so nice and spacious. Plenty of room to enjoy indoor time. Lots of outdoor options on and near the property. Highly recommend. Beautiful views of the bridges and the city.
Reviewed on Aug. 19, 2025

Courtyard New York Manhattan/ Midtown East
Manhattan
Price was CA $1,841, price is now CA $1,108 per person
CA $1,108
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,271 reviews)
Wonderful property, accesible to multiple subway stations. Walkable distance to plenty of sites and attractions. Great costumer service!
Reviewed on Aug. 20, 2025

Hotel St. James
Manhattan
Price was CA $1,301, price is now CA $812 per person
CA $812
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (6,194 reviews)
Absolutely fab hotel, really friendly staff, clean rooms with a very comfortable bed. Whilst it is not a modern hotel & it has no facilities such as bar it is just a few minutes walk from Times Square & is surrounded by restaurants.
I would recommend if your wanting a fab base in New York
Reviewed on Aug. 19, 2025
Ossining Hotel Deals

Windrose On Hudson
1 Old Albany Post Rd, Ossining, NY
Fully refundableReserve now, pay when you stay
The price is CA $228 per night from Aug 21 to Aug 22
CA $228
CA $254 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (9 reviews)
"Only one night so did not use the amenities. The refrigerator in the room died in the night so lost my leftovers. The room was clean and the staff was helpful. The shower function was strange. I would stay there again."
Reviewed on Aug. 12, 2025

Hampton Inn White Plains/Tarrytown
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Sep 1 to Sep 2
CA $176
CA $201 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,126 reviews)
"Pool not in service. Concrete around pool and walk to parking lot in poor shape. Excellent breakfast and well staffed"
Reviewed on Aug. 19, 2025

Royal Regency Hotel
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Sep 1 to Sep 2
CA $153
CA $188 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (2,216 reviews)
"Great Room. Hotel is close to the mall and the freeway. We definitely return."
Reviewed on Aug. 18, 2025
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.
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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.