Ossining Vacations from $547

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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 $989, price is now $547 per person
$547
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,593 reviews)
Servicio y localización

Reviewed on Jun 17, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was $4,067, price is now $1,559 per person
$1,559
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 New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $995, price is now $553 per person
$553
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,063 reviews)
Good location, big breakfast buffet that was decent, loved happy hour at the bar. The hall way to the room seemed a little dirty or musty to us and the room was pretty decent but the shower drain seemed clogged as it drained slowly and it was kinda awkward taking a shower because the toilet and shower is surrounded by frosted glass and when your showering everyone in the room gets a shadow show of you showering. I guess that’s ok for couples but if you are there with a family or friends then it is different level. lol but all in all we enjoyed it and we would stay again

Reviewed on Jun 17, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,566, price is now $1,473 per person
$1,473
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.

Reviewed on Jun 6, 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 $2,612, price is now $1,520 per person
$1,520
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (680 reviews)
Fantastic location, beautiful rooms, immaculate condition and the most amazing views

Reviewed on Jun 8, 2026

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Stay near popular Ossining attractions

Rest stop area beside interstate highway where travelers rest and sight see Tioga Reservoir and Dam in Pennsylvania New York state border

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
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $230 total per night from Jun 21 to Jun 22
$230 total
Jun 21 - Jun 22
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
$135 nightly
The price is $155 total per night from Jun 28 to Jun 29
$155 total
Jun 28 - Jun 29
Total with taxes and fees
8.4/10 Very Good! (1,733 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
Fully refundableReserve now, pay when you stay
$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! (1,129 reviews)
"This was a magnificent stay! The hotel is perfect!! Amazing location, excellent service! Rooms are comfortable and spacious, I recommend this property for anyone that wants to have an historical and enchanted stay!!!"

Reviewed on Jun 16, 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 $547 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.