Ossining Vacations from $748

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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
Price was $1,194, price is now $748 per person
$748
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The lifts take too long. Breakfast is a disaster. The bar is poor. Location ok. Luggage staff great.

Reviewed on Nov 15, 2026

Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Price was $2,024, price is now $1,187 per person
$1,187
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
8/10 Very Good! (1,000 reviews)
Completely caught off guard by this property: The Expedia photos looked great, the lobby was fine but the actual room was shabby and sub-par. The room and bathroom had the bare minimum amenities, smelled of stale cigarette smoke and was generally below expectations. Probably ok for a budget vacationer but I’m making a note to avoid this for a work stay.

Reviewed on Nov 11, 2026

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,808, price is now $1,651 per person
$1,651
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was $1,219, price is now $759 per person
$759
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was $2,091, price is now $1,309 per person
$1,309
per person
Jan 17 - Jan 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

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Stay near popular Ossining attractions

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.
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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
$164 nightly
The price is $183 total per night from Nov 22 to Nov 23
$183 total
Nov 22 - Nov 23
Total with taxes and fees
8.6/10 Excellent! (286 reviews)
"awesome"

Reviewed on Nov 15, 2026

Windrose On Hudson
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $150 total per night from Nov 18 to Nov 19
$150 total
Nov 18 - Nov 19
Total with taxes and fees
7.2/10 Good! (1,263 reviews)
"The room appeared to be clean but smell of cigarette smoke was strong"

Reviewed on Nov 14, 2026

LIV Hotel Bronx - Newly Built
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $227 total per night from Nov 19 to Nov 20
$227 total
Nov 19 - Nov 20
Total with taxes and fees
8.2/10 Very Good! (1,437 reviews)
"While the room was clean and the grounds nice to walk around, unfortunately the surrounding amenities were noticeable run down and needed some maintenance. The pool area and sauna have seen better days. The pool towels hadn't been dried properly and were all damp."

Reviewed on Nov 14, 2026

Tarrytown House Estate
See all 1,224 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 $748 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.