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.
Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Price was €1,654, price is now €925 per person
€925
per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,083 reviews)
Excellent location and great staff

Reviewed on 26 Aug 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €2,620, price is now €1,399 per person
€1,399
per person
18 Oct - 24 Oct
found 17 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
It was a very smooth experience. Checkin and checkout. Very good grab and go options luggage storage service helped us a lot. The staff were very helpful and accommodating. They were also open for a last minute change to reservation. The rooms are very good and pretty new. Spacious for where we are talking about.

Reviewed on 26 Aug 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was €5,457, price is now €2,938 per person
€2,938
per person
29 Oct - 5 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (1,001 reviews)
Exceedingly above my expectations

Reviewed on 31 Jul 2025

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Price was €2,371, price is now €1,330 per person
€1,330
per person
9 Oct - 14 Oct
found 24 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,589 reviews)
Facilities are great. Room was excellent. Food was very good.

Reviewed on 25 Aug 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,884, price is now €1,080 per person
€1,080
per person
18 Oct - 24 Oct
found 17 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8/10 Very Good! (2,142 reviews)
This hotel offers some rooms with a kitchen so you can prepare your own meals if, like me, you prefer to keep your costs low by eating in instead of out. The room I had was perfect for that. Check-in was easy and quick; and the location was quite convenient for me.

Reviewed on 25 Aug 2025

Top hotels in Ossining

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Old Albany Post Rd, Ossining, NY
Fully refundableReserve now, pay when you stay
The price is €210 per night from 28 Aug to 29 Aug
€210
28 Aug - 29 Aug
includes taxes & fees
8.2/10 Very Good! (9 reviews)
"Only one night so did not use the amenities. The refrigerator in the room died in the night so lost my leftovers. The room was clean and the staff was helpful. The shower function was strange. I would stay there again."

Reviewed on 12 Aug 2025

Windrose On Hudson
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is €134 per night from 14 Sept to 15 Sept
€134
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (1,131 reviews)
Good hotel but rude guests
"The staff were very nice and helpful. The room could do with a refresh but was clean and comfortable. The noise from the roads outside was loud making sleep harder. The dog barking on one side and the constant arguing on the other side didn't help. More soundproofing would be nice. Breakfast and ..."

Reviewed on 22 Aug 2025

Hampton Inn White Plains/Tarrytown
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 €118 per night from 1 Sept to 2 Sept
€118
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (2,222 reviews)
"Was very clean a"

Reviewed on 24 Aug 2025

Royal Regency Hotel
See all 1,214 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 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 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 €925 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.