Ossining Vacations from $363

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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.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was $630, price is now $363 per person
$363
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,144 reviews)
AC was on the fritz and bathroom fan didn’t work. These two made for a humid night on the 12th floor. The location was perfect for our Central Park exploration.

Reviewed on Jun 15, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was $4,035, price is now $1,527 per person
$1,527
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,721, price is now $828 per person
$828
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,593 reviews)
It's a good place to stay, relax after a fun sightseeing in NYC. I had a good night sleep. Highly recommended!

Reviewed on Jun 16, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,615, price is now $1,470 per person
$1,470
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (679 reviews)
Fantastic location, beautiful rooms, immaculate condition and the most amazing views

Reviewed on Jun 8, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was $820, price is now $474 per person
$474
per person
Jul 25 - Jul 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,435 reviews)
The location was great. Times square at the corner.... No mini fridge though or ice machine.... Vintage style aesthetics. Shops next door and across street.

Reviewed on Jun 15, 2026

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Discover the most popular places to visit in Ossining

Teatown Lake Reservation

Teatown Lake Reservation

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

Sing Sing Correctional Facility

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

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
$202 nightly
The price is $224 total per night from Jun 28 to Jun 29
$224 total
Jun 28 - Jun 29
Total with taxes and fees
8.4/10 Very Good! (170 reviews)
"Well, it’s almost as if on the weekend the hotel doesn’t know it’s a hotel but the rooms are spotless. The property is the most beautiful property I’ve ever seen, but it’s very arbitrary if they want to serve food that day or not or even if the bar is open and signage is just terrible but other than ..."

Reviewed on Jun 15, 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
$144 nightly
The price is $164 total per night from Jun 28 to Jun 29
$164 total
Jun 28 - Jun 29
Total with taxes and fees
8.4/10 Very Good! (1,729 reviews)
"The room smelled musty. The walls were thin so I heard a lot hallway noise and noise from neighboring rooms."

Reviewed on Jun 14, 2026

Baymont by Wyndham White Plains - Elmsford
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
$163 nightly
The price is $186 total per night from Jun 28 to Jun 29
$186 total
Jun 28 - Jun 29
Total with taxes and fees
8.2/10 Very Good! (1,127 reviews)
"I found a mysterious yellow pill on the floor of our hotel room, where my two babies were staying with me and my husband. The hotel knew that I was traveling with babies, as I called 5x to make sure we were all set with their crib beds and early check in. I am extremely disappointed that our safety ..."

Reviewed on Jun 15, 2026

Tarrytown House Estate
See all 1,338 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 $363 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.