Ossining Vacations from $785

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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.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,397, price is now $785 per person
$785
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,768 reviews)

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $2,345, price is now $1,292 per person
$1,292
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (1,725 reviews)

Vintedge Residences

Vintedge Residences

2 out of 5
Save 100% on your flight
Price was $1,605, price is now $894 per person
$894
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
No reviews

The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was $1,824, price is now $1,078 per person
$1,078
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)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,982, price is now $1,764 per person
$1,764
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,007 reviews)
This hotel is something out of the world beautiful

Reviewed on Jul 29, 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 Aug 2 to Aug 3
$220 total
Aug 2 - Aug 3
Total with taxes and fees
8.6/10 Excellent! (205 reviews)
"Awful. I have traveled on five continents for work and pleasure. This may be the worst hotel I have ever stayed in. It is desperately in need of a deep clean and renovation. I have still not - three days after checking out- received the refund of the $50 I was charged for “incidentals” when I arrived, ..."

Reviewed on Jul 30, 2026

Windrose On Hudson
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $196 total per night from Aug 2 to Aug 3
$196 total
Aug 2 - Aug 3
Total with taxes and fees
8.2/10 Very Good! (1,207 reviews)
"This hotel looked so cute in the pictures. We got there at 8:30 at night, stopping overnight on our drive from Boston. The hotel smelled so musty, our room was so far away with so many turns and 3 floors of steps. Room was old, bug crawling down the wall. We didn't even stay. I just wasn't comfortable ..."

Reviewed on Jul 29, 2026

Tarrytown House Estate
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
$127 nightly
The price is $145 total per night from Aug 23 to Aug 24
$145 total
Aug 23 - Aug 24
Total with taxes and fees
8.4/10 Very Good! (1,782 reviews)
"Nice and clean. The AC worked perfectly and was quiet. Great water pressure in the shower. The breakfast was pretty good. I would be happy to come back next year."

Reviewed on Jul 29, 2026

Baymont by Wyndham White Plains - Elmsford
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 $785 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.