Ossining Vacations from $679
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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.
The Latest Ossining vacation packages
Price found within the past 48 hours. Click for updated prices.
The Towers at Lotte New York Palace
Manhattan
Save 100% on your flight
Price was $6,111, price is now $3,463 per person
$3,463
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (689 reviews)
Beautiful hotel. Great experience.
Reviewed on Jul 30, 2026
The Wall Street Hotel
Manhattan
Price was $1,971, price is now $1,145 per person
$1,145
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (719 reviews)
Very nice hotel. The staff were all super friendly and helpful. Would definitely stay here again.
Reviewed on Aug 2, 2026
Stay near popular Ossining attractions
Ossining Hotel Deals
Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
$206 nightly
The price is $230 total per night from Aug 9 to Aug 10
$230 total
Aug 9 - Aug 10
Total with taxes and fees
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $205 total per night from Aug 16 to Aug 17
$205 total
Aug 16 - Aug 17
Total with taxes and fees
8.2/10 Very Good! (1,197 reviews)
"Had a midweek break from the city for two days and wish I could say wife and I would return. Bathroom absolutely disgusting with hairs in shower. Just 2 towels , 1 hand towel and 1 washcloth for 2 people. NO BATHMAT. Asked housekeeping for extra towels and told they were low on supply. SMH....... ..."
Reviewed on Aug 2, 2026
Baymont by Wyndham White Plains - Elmsford
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $142 total per night from Aug 30 to Aug 31
$142 total
Aug 30 - Aug 31
Total with taxes and fees
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.
Find the Best Ossining Vacation Packages
Ossining Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | LaGuardia Airport (LGA) |
Population | 25,400 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Franklin D. Roosevelt State Park, Paramount Hudson Valley Theater and Rockefeller Archive Center |
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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.