Ossining Holidays

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    Save up to €900 when you book a flight and hotel together*

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Top Flight + Hotel Deals in Ossining

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was €1,370, price is now €910 per person
€910
per person
3 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
I love this hotel! Start here every time. The housekeeper Norma is lovely. The staff is always so helpful and nice. I always feel safe here.

Reviewed on 14 Jul 2026

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,884, price is now €1,115 per person
€1,115
per person
16 Sept - 21 Sept
found 8 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8/10 Very good! (2,471 reviews)
Great place to stay for the price!

Reviewed on 14 Jul 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,817, price is now €1,192 per person
€1,192
per person
3 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,130 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €1,733, price is now €1,148 per person
€1,148
per person
3 Sept - 7 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
Managed to get us a room on extremely short notice. Fantastic place, great staff, and located right in the heart of Manhattan!

Reviewed on 14 Jul 2026

The Ridge Hotel

The Ridge Hotel

3 out of 5
Manhattan
Save 100% on your flight
Price was €1,574, price is now €1,086 per person
€1,086
per person
16 Sept - 21 Sept
found 8 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
8.2/10 Very good! (1,156 reviews)
The air conditioning was awesome! My room was set at 63 and it was great. The fridge was cold as well. No hair dryer or hangers, had to ask for them. Room seemed clean enough but my remote control was so gross, looked like it was cleaned for years. There was dust over window sills and on top of hooks.

Reviewed on 14 Jul 2026

Top hotels in Ossining

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
The price is €202 per night from 19 Jul to 20 Jul
€202
19 Jul - 20 Jul
includes taxes & fees
8.6/10 Excellent! (192 reviews)
"Overall, the wife and I had a great experience. It would be nice if there was a cafeteria on the premises. The bartender was very helpful and the room was very nice."

Reviewed on 14 Jul 2026

Windrose On Hudson
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 €84 per night from 3 Aug to 4 Aug
€84
3 Aug - 4 Aug
includes taxes & fees
6.2/10 (2,277 reviews)
"No washer dryer available rugs needed a good scrub limited towel I won’t back"

Reviewed on 14 Jul 2026

Armoni Inn & Suites
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 €215 per night from 16 Jul to 17 Jul
€215
16 Jul - 17 Jul
includes taxes & fees
8.8/10 Excellent! (1,333 reviews)
"Overall great stay. Food, bar, staff, room all nice"

Reviewed on 13 Jul 2026

Sonesta White Plains Downtown
See all 1,336 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.

Stay near popular Ossining attractions

Travelers Rest

This historic former stagecoach stop serves exceptional American and German cuisine in elegant, fireplace-lit dining rooms. Stroll through the landscaped gardens with waterfalls before your memorable meal.
See properties

Frequently asked questions

How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from €910 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.

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