Ossining Holidays from NZ$3,881

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The Latest Ossining Holiday Deals

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

Hotel St. James

3 out of 5
Manhattan
Price was NZ$5,387, price is now NZ$3,881 per person
NZ$3,881
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Wellington (WLG) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
No fan in bathroom

Reviewed on 17 July 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was NZ$7,397, price is now NZ$4,807 per person
NZ$4,807
per person
29 Aug - 5 Sept
found 13 hours ago
Return direct flight included
Wellington (WLG) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
It may have been because of FIFA…in the mornings trying to go down for breakfast was a struggle…the elevators were packed and we had to let several (3-4) go by before finally pushing onto the elevator. The guests were just as polite as the staff…everyone understood.

Reviewed on 17 July 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was NZ$6,419, price is now NZ$4,332 per person
NZ$4,332
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Wellington (WLG) to New York (JFK)
9.2/10 Wonderful! (3,746 reviews)
We had a beautiful view of the city and the iconic New Years Eve ball. The bed was very comfortable and breakfast was delicious. Will definitely stay here again.

Reviewed on 17 July 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was NZ$6,270, price is now NZ$4,246 per person
NZ$4,246
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Wellington (WLG) to New York (JFK)
9.6/10 Exceptional! (1,617 reviews)
This hotel is adorable. Great location. Rooms are a great size. We will be back!

Reviewed on 17 July 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was NZ$7,095, price is now NZ$4,943 per person
NZ$4,943
per person
29 Aug - 5 Sept
found 11 hours ago
Return direct flight included
Wellington (WLG) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
Loved the front desk staff and the bell staff. Hated that I was charged $210 for parking when I didn’t even have a car there. Still waiting to be refunded. They said they need to investigate. Smh.

Reviewed on 17 July 2026

Ossining Holiday

Our pick of the best Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
The price is NZ$392 per night from 21 July to 22 July
NZ$392
21 July - 22 July
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 July 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 NZ$174 per night from 20 July to 21 July
NZ$174
20 July - 21 July
includes taxes & fees
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 NZ$369 per night from 16 Aug to 17 Aug
NZ$369
16 Aug - 17 Aug
includes taxes & fees
8.8/10 Excellent! (1,334 reviews)
"Overall it was clean and quiet"

Reviewed on 17 July 2026

Sonesta White Plains Downtown
See all 1,327 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 NZ$3,881 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.