Ossining Holidays

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Top Flight + Hotel Deals in Ossining

Price found within the past 48 hours. Click for updated prices.
The William Vale

The William Vale

5 out of 5
per person
29 Mar - 3 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,003 reviews)
Accommodations were very nice. Courteous & professional staff were attentive and welcoming.

Reviewed on 4 Feb 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
29 Mar - 3 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,002 reviews)
We loved our stay at 1 Hotel Brooklyn Bridge. It is not your basic hotel - the location, the design and the views make it a one of a kind experience!

Reviewed on 3 Feb 2025

Millennium Hilton New York One UN Plaza

Millennium Hilton New York One UN Plaza

4 out of 5
Manhattan
Save 100% on your flight
per person
13 Apr - 19 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.2/10 Very Good! (1,662 reviews)
Not bad. Very clean.

Reviewed on 4 Feb 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
30 Mar - 5 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.8/10 Exceptional! (1,101 reviews)
This property is fantastic! It’s not too big, which is great. The shower was incredible, and the bed was super comfortable. The location is also amazing - Juliet’s balcony is the perfect spot to wake up every morning and enjoy the view.

Reviewed on 7 Feb 2025

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
29 Mar - 3 Apr
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (598 reviews)
Staff made us feel so welcomed, comfortable, and practically like royalty. Room was very spacious compared to a typical hotel room. Plenty of closet space. Location was great. Close to shopping and a couple blocks from Metro. Walking distance to Times Square and Central Park. For a 5 star hotel, the room showed quite of bit of wear and tear.

Reviewed on 4 Jan 2025

Top hotels in Ossining

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 €61 per night from 21 Feb to 22 Feb
€61
includes taxes & fees
21 Feb - 22 Feb
6/10 (1,836 reviews)
"Nice, clean place to stay, weather for work or leisure. The hotel is very quiet, there's pool on site. Good customer service safe parking and dining right around the corner off the property. There's a bank next door for easy transaction. I highly recommend this hotel."

Reviewed on 4 Feb 2025

Armoni Inn & Suites
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 €128 per night from 23 Feb to 24 Feb
€128
includes taxes & fees
23 Feb - 24 Feb
8.2/10 Very Good! (1,959 reviews)
"Wonderful"

Reviewed on 3 Feb 2025

Royal Regency Hotel
Sonesta White Plains Downtown
Sonesta White Plains Downtown
4 out of 5
66 Hale Ave, White Plains, NY
Fully refundableReserve now, pay when you stay
The price is €203 per night from 2 Mar to 3 Mar
€203
includes taxes & fees
2 Mar - 3 Mar
8.6/10 Excellent! (1,163 reviews)
"Beautiful, clean and in a great area. Perfect for recreational and business travelers."

Reviewed on 6 Feb 2025

Sonesta White Plains Downtown
See all 1,096 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 €898 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 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.