Ossining Vacations from $295

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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.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $660, price is now $295 per person
$295
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Room was great, clean, and staff was always willing to go above and beyond.

Reviewed on Dec 23, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $877, price is now $447 per person
$447
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Amazing room with door out to courtyard, excellent for walking the dog. Always a great stay when we are here. Excellent food at on-site restaurant, beds are so comfy. Everyone is so nice to the dog when we bring him. Great location.

Reviewed on Dec 23, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $654, price is now $344 per person
$344
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
Very clean and comfortable

Reviewed on Dec 24, 2025

New York Marriott Downtown

New York Marriott Downtown

4 out of 5
Manhattan
Save 100% on your flight
Price was $918, price is now $492 per person
$492
per person
Feb 26 - Mar 2
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
It was nice. The lobby was a quite small and a couple of the front desk people seemed a little aggravated with the amount of questions we asked.

Reviewed on Dec 22, 2025

Fouquet's New York

Fouquet's New York

5 out of 5
Manhattan
Price was $1,546, price is now $837 per person
$837
per person
Mar 2 - Mar 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (60 reviews)
Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time.

Reviewed on Oct 10, 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 Shady Lane Farm Road Ossining NY
$197 nightly
The price is $220 total per night from Jan 4 to Jan 5
$220 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8/10 Very Good! (102 reviews)
Great

Reviewed on Dec 20, 2025

Windrose On Hudson
Ramada by Wyndham Bronx

Ramada by Wyndham Bronx

3 out of 5
1000 Baychester Ave Bronx NY
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $154 total per night from Jan 11 to Jan 12
$154 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Good

Reviewed on Dec 20, 2025

Ramada by Wyndham Bronx
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $122 total per night from Jan 22 to Jan 23
$122 total
Jan 22 - Jan 23, 2026
Total with taxes and fees
8.2/10 Very Good! (2,433 reviews)
Clean room, great breakfast and great service.

Reviewed on Dec 22, 2025

Royal Regency Hotel
See all 1,312 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 $295 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.