Ossining Holidays

Photo by Linda Zanetti

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Top Flight + Hotel Deals in Ossining

Price found within the past 48 hours. Click for updated prices.
Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Save 100% on your flight
per person
3 Oct - 8 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (8 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on 25 Jun 2025

The Knickerbocker Hotel

The Knickerbocker Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,535 reviews)
Staff friendly and helpful. Especially Paola and Marcelo. Hotel is in nice location, clean and rooms are big.

Reviewed on 22 Jul 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
3 Oct - 8 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.8/10 Exceptional! (1,259 reviews)
Very convenient to shopping and restaurants, and the staff were excellent

Reviewed on 3 Aug 2025

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
Save 100% on your flight
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (19 reviews)
During my stay in NYC I couldn’t have stayed at a better place. Even though guests share the bathroom, it was not a big deal and the staff were very nice and helpful. I will definitely stay there again.

Reviewed on 19 Jul 2025

Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Save 100% on your flight
per person
3 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,487 reviews)
Lovely hotel in an amazing neighborhood. So convenient and quiet. Room was clean and very comfortable.

Reviewed on 3 Aug 2025

Top hotels in Ossining

Windrose On Hudson

Windrose On Hudson

2 out of 5
1 Old Albany Post Rd, Ossining, NY
The price is €239 per night from 17 Aug to 18 Aug
€239
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (7 reviews)
"Very unique property. It's a big onsite property like a campus - and they have carved out a hotel area. Very new, well kept buildings and grounds. The location is actually on a long hiking trail with beautiful views. The room wasn't huge but very clean and beautiful floor to ceiling windows. Staff ..."

Reviewed on 30 Jul 2025

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
The price is €69 per night from 2 Sept to 3 Sept
€69
2 Sept - 3 Sept
includes taxes & fees
6/10 (1,980 reviews)
"Good"

Reviewed on 20 Jul 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 €142 per night from 10 Aug to 11 Aug
€142
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (1,383 reviews)
Visit stay
"For me it was close to the hospital and the staff at the hotel was friendly and gave me a good suggestions for places to eat."

Reviewed on 29 Jul 2025

Baymont by Wyndham White Plains - Elmsford
See all 1,204 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.

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 family-friendly 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 quaint area's riverfront and enjoy its top-notch restaurants.

Sing Sing Prison Museum

Hudson Hills Golf Course

Enjoy a round of golf in Ossining at Hudson Hills Golf Course. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Hudson Hills Golf Course

Frequently asked questions

How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from €895 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.

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