Ossining Holidays from AU$1,537

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Your Ossining Holiday

With one of our holiday packages to Ossining, you'll find countless opportunities for fun and relaxation. There's tons to experience, including its rich history and spectacular views. Make your trip to Ossining even more fun by going sightseeing. Van Cortlandt Manor, Sleepy Hollow Cemetery and Tarrytown Music Hall are among the popular attractions worth exploring. Don't delay your visit to this city any longer. Your ultimate Ossining holiday is only a few clicks away with Expedia.

The Latest Ossining Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Save 100% on your flight
per person
20 May - 23 May
found 20 hours ago
Return direct flight included
Montreal (YUL) to New York (JFK)
8.6/10 Excellent! (1,388 reviews)
Great property - great location.

Reviewed on 23 Mar. 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
5 Jun - 12 Jun
found 10 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.8/10 Exceptional! (1,120 reviews)
We loved the location between Chinatown and little Italy. It was only a few blocks to SoHo shopping and the subway station. The staff was very nice and the room was small but perfect for me and my daughter. The lobby had a coffee and ice machine and there was a little fridge with soda and sparkling water for a couple bucks. Nothing Wow but it was a great stay. I will definitely book there again when we return to NYC

Reviewed on 24 Mar. 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
20 May - 23 May
found 20 hours ago
Return direct flight included
Montreal (YUL) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
Its an amazing hotel, so clean and green and everything is just so chic!

Reviewed on 24 Mar. 2025

The Plaza - A Fairmont Managed Hotel

The Plaza - A Fairmont Managed Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
20 May - 23 May
found 20 hours ago
Return direct flight included
Montreal (YUL) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
The best like always , Mr.loae was the best in hotel and he were so kind and helpful 🙏🙏

Reviewed on 13 Mar. 2025

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
20 May - 23 May
found 20 hours ago
Return direct flight included
Montreal (YUL) to New York (JFK)
9/10 Wonderful! (1,366 reviews)
The best of all, is the people who work there

Reviewed on 21 Mar. 2025

Ossining Holiday

Ossining Essential Information

Language
English
Currency
U.S dollars
Closest Airport
LaGuardia Airport (LGA)
Population
25,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Bear Mountain State Park, Franklin D. Roosevelt State Park and Paramount Hudson Valley Theatre

Our pick of the best Ossining Hotel Deals

Hampton Inn & Suites Yonkers
Hampton Inn & Suites Yonkers
2.5 out of 5
160 Corporate Blvd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 6 Apr to 7 Apr
AU$206
includes taxes & fees
6 Apr - 7 Apr
8/10 Very Good! (1,294 reviews)
"It was great!"

Reviewed on 22 Mar. 2025

Hampton Inn & Suites Yonkers
Armoni Inn & Suites
Armoni Inn & Suites
3.5 out of 5
329 Route 303, Orangeburg, NY
Fully refundableReserve now, pay when you stay
The price is AU$158 per night from 7 Apr to 8 Apr
AU$158
includes taxes & fees
7 Apr - 8 Apr
6/10 (1,916 reviews)

Reviewed on 22 Mar. 2025

Armoni Inn & Suites
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
The price is AU$217 per night from 20 Apr to 21 Apr
AU$217
includes taxes & fees
20 Apr - 21 Apr
8.2/10 Very Good! (1,258 reviews)
"Clean, quiet and about a mile away from westchester med which made it incredibly convenient for someone not from the area and having my husband hospitalized"

Reviewed on 24 Mar. 2025

Baymont by Wyndham White Plains - Elmsford
See all 1,127 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from AU$1,537 on Expedia. However, how much your holiday to Ossining costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossining?
The off-season is the best time to head to Ossining if you’re hoping to keep costs down. Another tip for scoring cheap Ossining holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Ossining?
To fully enjoy your Ossining holiday, we recommend staying for 5 days. Divide your time between visiting Teatown Lake Reservation, Kitchawan Preserve and other top attractions, in addition to experiencing neighbourhoods like Town of Mount Pleasant and Pleasantville. If you’ve got some time to spare, add a tour or day trip to your Ossining holiday itinerary.
Is it worth booking a holiday package to Ossining?
Ossining has everything you need for an unforgettable escape. Get your Ossining holiday off to a flying start by visiting top attractions like Louis Engel Waterfront Park.
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 holiday package well in advance.
Is it cheaper to book an Ossining holiday as a package?
You can enjoy significant savings on your Ossining retreat by booking a personalised holiday 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 holiday 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.
How to plan a trip to Ossining?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Ossining.
  2. Budget wisely: Besides the price of your accommodation, you’ll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Ossining.
  3. Set the duration of your trip: Start by listing all the attractions and activities you’d like to get to in Ossining. Then, estimate how long you’ll need at each, including any travel time.
  4. Bundle your accommodation and airfare: After you’ve settled on your dates and duration, lock in the ideal Ossining holiday package for you.

Discover the most popular places to visit in Ossining

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.