Ossining Vacations from $561

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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.
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $976, price is now $561 per person
$561
per person
Sep 17 - Sep 20
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (1,710 reviews)
.

Reviewed on Jul 10, 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,014, price is now $577 per person
$577
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
We were very pleasantly surprised by how cool the hotel was! Entering, you realize that it is very stylish from the lobby area to the rooms. The room we rented was a large studio with a queen bed and a pull-out sofa. You could smell how clean it was upon entering the room. It is bare bones but that's exactly what we needed. It was so interesting that the shower was right there in the room and you could see that someone was in there but you couldn't see them. It worked great. The front desk staff recommended a local restaurant for us and it was amazing! No complaints whatsoever. I would highly recommend the hotel for anyone staying in the area.

Reviewed on Jul 9, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,684, price is now $1,534 per person
$1,534
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 2026

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $2,924, price is now $1,686 per person
$1,686
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
3/10 (4 reviews)

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,072, price is now $619 per person
$619
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (3,239 reviews)
Very convenient location and very attentive staff. Thanks for another great stay!

Reviewed on Jul 10, 2026

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Stay near popular Ossining attractions

A dam with a reservoir, surrounded by autumn foliage and hills.

Travelers Rest

This historic former stagecoach stop serves exceptional American and German cuisine in elegant, fireplace-lit dining rooms. Stroll through the landscaped gardens with waterfalls before your memorable meal.
See properties

Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
$197 nightly
The price is $220 total per night from Jul 12 to Jul 13
$220 total
Jul 12 - Jul 13
Total with taxes and fees
8.6/10 Excellent! (186 reviews)
"Beautiful location and good property for YOUNG, ATHLETIC folks able to navigate the hills and distances between venues. Not so good for those with disabilities or just tired old knees, hips and hearts! Doors very heavy and w/o automated openers, shower floors very slippery, only two USB outlets in ..."

Reviewed on Jul 8, 2026

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Jul 26 to Jul 27
$90 total
Jul 26 - Jul 27
Total with taxes and fees
6/10 (2,289 reviews)
"There are bed bugs in my room I woke up with something biting me in the middle of the night and I had bumps all over my legs and on my back. I also saw a small bug that might have been a bed bug crawling on my sheets. They need an exterminator pronto or else they're going to start losing customers. ..."

Reviewed on Jul 9, 2026

Armoni Inn & Suites
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $223 total per night from Aug 2 to Aug 3
$223 total
Aug 2 - Aug 3
Total with taxes and fees
8.8/10 Excellent! (1,326 reviews)
"I enjoyed my stay down to the pool but is far from the main museums"

Reviewed on Jul 9, 2026

Sonesta White Plains Downtown
See all 1,327 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.

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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Frequently asked questions

How much does an Ossining vacation package cost?
You can snap up a vacation package to this popular destination from $561 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.

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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.