Ossining Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to €185 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Ossining

Price found within the past 48 hours. Click for updated prices.
Now Now NoHo

Now Now NoHo

2 out of 5
Manhattan
per person
26 Jun - 30 Jun
found 4 hours ago
Return direct flight included
Istanbul (IST) to New York (JFK)
No reviews
You pay for exactly what you get, maybe even more. It’s cozy and comfortable, clean and safe. Staff is always smiling and happy to help!

Reviewed on 7 Apr 2025

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
26 Jun - 30 Jun
found 4 hours ago
Return direct flight included
Istanbul (IST) to New York (JFK)
9/10 Wonderful! (1,382 reviews)
Excellent time, and great service

Reviewed on 9 Apr 2025

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
per person
26 Jun - 30 Jun
found 4 hours ago
Return direct flight included
Istanbul (IST) to New York (JFK)
8.2/10 Very Good! (2,806 reviews)
Amazing hotel, and staff. Always very clean.

Reviewed on 7 Apr 2025

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
per person
26 Jun - 30 Jun
found 4 hours ago
Return direct flight included
Istanbul (IST) to New York (JFK)
8.4/10 Very Good! (1,104 reviews)
Staff was wonderful and the rooms were spacious. Definitely a great spot at a budget friendly rate.

Reviewed on 8 Apr 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
per person
26 Jun - 30 Jun
found 4 hours ago
Return direct flight included
Istanbul (IST) to New York (JFK)
8/10 Very Good! (2,018 reviews)
The room served our purpose; close to everything we wanted to see. However, there were amenities lacking and one of the staff members was very unhelpful and did not seem to care too much about anything. Recommended stay if you plan on only using the room for sleeping and storing luggage.

Reviewed on 8 Apr 2025

Top hotels in Ossining

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 €127 per night from 21 Apr to 22 Apr
€127
includes taxes & fees
21 Apr - 22 Apr
8/10 Very Good! (1,332 reviews)
"Nice room and facilities excellent, but ice machine bit teribble . I went to 3 foor is broken then 2 is empty so going 1 floor alot of works because its in corner and my room is in other corner. Good breakfast and the lady who incharge very nice. She Refill and clean area dining properly."

Reviewed on 10 Apr 2025

Hampton Inn & Suites Yonkers
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 €117 per night from 20 Apr to 21 Apr
€117
includes taxes & fees
20 Apr - 21 Apr
8.2/10 Very Good! (1,282 reviews)
Exceptional service
"The hotel experience was exceptional. The only thing i would suggest is a wider variety of breakfast food."

Reviewed on 6 Apr 2025

Baymont by Wyndham White Plains - Elmsford
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is €91 per night from 17 Apr to 18 Apr
€91
includes taxes & fees
17 Apr - 18 Apr
8.4/10 Very Good! (1,577 reviews)
"The staff was friendly and helpful, the hhotel is a bit outdated with decor and furniture from the 90s but this is shown on the site as well. The highway is close about 1 block away which can be great but bad with noises. But besides that not a bad place for a night."

Reviewed on 6 Apr 2025

Amsterdam Hotel
See all 1,156 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.

Frequently asked questions

How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from €654 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.

Popular places to visit

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

Sing Sing Prison Museum

You can spend time studying the exhibits at Sing Sing Prison Museum in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Sing Sing Prison Museum

Nelson Park

Nelson Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants.

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