Ossining Holidays from AU$2,363

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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.
Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
5 Jun - 10 Jun
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
7.6/10 Good! (749 reviews)
It was cool rooms was small so recommend if solo traveling like i did clean af and friendly staff ac/heater was okay tho over all 10/10 they pass.

Reviewed on 21 Mar. 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
5 Jun - 10 Jun
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.8/10 Exceptional! (1,133 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

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
per person
5 Jun - 10 Jun
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.2/10 Very Good! (2,806 reviews)
The larger rooms were perfect for our larger group

Reviewed on 27 Mar. 2025

Tuscany by LuxUrban

Tuscany by LuxUrban

3 out of 5
Manhattan
per person
5 Jun - 10 Jun
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.2/10 Very Good! (1,007 reviews)
Great place, very clean room. Staff was very friendly and helpful

Reviewed on 26 Mar. 2025

The Washington by LuxUrban

The Washington by LuxUrban

3 out of 5
Manhattan
per person
5 Jun - 10 Jun
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.2/10 Very Good! (1,013 reviews)
The Ritz is top notch stay and amazing service.

Reviewed on 24 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 13 Apr to 14 Apr
AU$206
includes taxes & fees
13 Apr - 14 Apr
8/10 Very Good! (1,298 reviews)
"Friendly staff. Great breakfast in the morning. Was questionable if bedding had “clean” sheets. Odor as soon as you come off elevator was awful."

Reviewed on 25 Mar. 2025

Hampton Inn & Suites Yonkers
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
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
8.4/10 Very Good! (1,573 reviews)
"Easy access. Great staff"

Reviewed on 25 Mar. 2025

Amsterdam Hotel
Royal Regency Hotel
Royal Regency Hotel
3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is AU$220 per night from 13 Apr to 14 Apr
AU$220
includes taxes & fees
13 Apr - 14 Apr
8.2/10 Very Good! (2,034 reviews)
"The place is very nice it's just it's very noisy when you're trying to sleep at night and in the morning maybe there's a way they can be more sound barriers but other than that great facility"

Reviewed on 23 Mar. 2025

Royal Regency Hotel
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$2,363 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.