Ossining Vacations from $350

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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 Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $696, price is now $350 per person
$350
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug 12, 2025

Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $742, price is now $361 per person
$361
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
8.4/10 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

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,216, price is now $1,202 per person
$1,202
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug 21, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,233, price is now $674 per person
$674
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,296 reviews)
I would definitely stay at this hotel again. Rooms were great! Location was convenient to everything, but also not in an area where the sidewalks were super crowded all the time. The staff and service were absolutely superb. HIghly recommend!

Reviewed on Aug 25, 2025

Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was $700, price is now $384 per person
$384
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,466 reviews)
Property is exceptional with amazing city views. A definte must. Access to nyc/wtc via path train is really close

Reviewed on Aug 24, 2025

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Discover the most popular places to visit in Ossining

Lovely spot in Westchester, NY

Teatown Lake Reservation

Explore the great outdoors at Teatown Lake Reservation, a lovely green space in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Teatown Lake Reservation

Sing Sing Correctional Facility

After visiting Sing Sing Correctional Facility, make a plan to see the other sights and activities in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Sing Sing Correctional Facility

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

Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Old Albany Post Rd, Ossining, NY
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $244 total per night from Aug 28 to Aug 29
$244 total
Aug 28 - Aug 29
Total with taxes and 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

Windrose On Hudson
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
$127 nightly
The price is $145 total per night from Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (1,128 reviews)
Good hotel but rude guests
"The staff were very nice and helpful. The room could do with a refresh but was clean and comfortable. The noise from the roads outside was loud making sleep harder. The dog barking on one side and the constant arguing on the other side didn't help. More soundproofing would be nice. Breakfast and ..."

Reviewed on Aug 22, 2025

Hampton Inn White Plains/Tarrytown
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $127 total per night from Sep 7 to Sep 8
$127 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (2,216 reviews)
"Room was nice and clean. It’s in residential area right front of private homes. Was bet noisy. Overall I was satisfied. Staff was friendly."

Reviewed on Aug 22, 2025

Royal Regency Hotel
See all 1,214 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.

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Frequently asked questions

How much does an Ossining vacation package cost?
You can snap up a vacation package to this popular destination from $350 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?
You can typically find reduced prices and greater availability in December, January and February. Browse our cheap Ossining vacation packages and you could land some great off-season deals.
How many days is enough for Ossining?
To get the most out of your Ossining vacation, we recommend booking for 6 days. Divide your time between visiting Louis Engel Waterfront Park, Teatown Lake Reservation and other must-see attractions, on top of exploring neighborhoods like Town of Mount Pleasant and Crotonville. If you've got some spare time, include a day trip in your Ossining vacation itinerary.
Is it worth booking a vacation package to Ossining?
Ossining is a good vacation destination with attractions like Sing Sing Correctional Facility among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, an Ossining vacation promises a good time for everyone.
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.
Does Expedia offer Book Now, Pay Later Ossining vacation packages?
If you're anything like us, you love going away but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Ossining vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.