Ossining Holidays from NZ$3,757

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The Latest Ossining Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

Manhattan
NZ$3,757
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Christchurch (CHC) to New York (JFK)
7.6/10 Good! (3,515 reviews)
Great location close to 96th street subway which took about 10 minutes to midtown. Plenty of shops for food and supplies, and street vendors close by-along Broadway, Central Park was only a few blocks away. The hotel was clean and relativly tidy maybe a little dated but still worth it and the bronze room, whilst a little small, was more than adequate.

Reviewed on 31 Aug 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

Manhattan
Save 100% on your flight
NZ$4,579
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Christchurch (CHC) to New York (JFK)
9.2/10 Wonderful! (3,936 reviews)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

Manhattan
Save 100% on your flight
NZ$4,518
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Christchurch (CHC) to New York (JFK)
9/10 Wonderful! (3,313 reviews)
Everything was excellent as well as location to Times square. High floor and great view. Clean and comfy. Breakfast excellent.

Reviewed on 31 Aug 2026

NobleDEN Hotel

NobleDEN Hotel

Manhattan
Save 100% on your flight
NZ$4,595
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Christchurch (CHC) to New York (JFK)
9.8/10 Exceptional! (1,662 reviews)
Loved this hotel! Would definitely come back. Staff was very welcoming and room was super cute. Good location close to little Italy and Chinatown. Loved the access to the rooftop.

Reviewed on 29 Aug 2026

Hotel Beacon

Hotel Beacon

Manhattan
NZ$5,464
per person
5 Oct - 12 Oct
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9.4/10 Exceptional! (1,511 reviews)

Ossining Holiday

Our pick of the best Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
NZ$349
27 Sept - 28 Sept
includes taxes & fees
Windrose On Hudson
Tarrytown House Estate

Tarrytown House Estate

49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
NZ$350
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very good! (1,272 reviews)
"The grounds and outside lawns and gardens are beautiful, but the interior seems somewhat old and run down."

Reviewed on 30 Aug 2026

Tarrytown House Estate
Royal Regency Hotel

Royal Regency Hotel

165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
NZ$257
13 Sept - 14 Sept
includes taxes & fees
8.6/10 Excellent! (2,850 reviews)
"It was a great place to be"

Reviewed on 31 Aug 2026

Royal Regency Hotel
See all 1,279 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

A misty lake surrounded by trees with sunlight filtering through the leaves.
Photo by louann ohora

Teatown Lake Reservation

This 1,000-acre nature preserve features diverse ecosystems along scenic trails. Explore the floating boardwalk across the lake for wildlife viewing and see the island's native wildflower collection.
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A dam with a reservoir, surrounded by autumn foliage and hills.

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.
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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.
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Hudson Hills Golf Course

Nestled in Ossining's rolling terrain, this Mark Mungeam-designed course challenges players with strategic bunkers and undulating fairways. Enjoy Hudson River Valley views while navigating the thoughtful 18 holes.
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Sing Sing Prison Museum

Step inside America's most infamous prison at the Sing Sing Prison Museum, opening in 2025 for its 200th anniversary. Explore artefacts and stories illuminating incarceration and rehabilitation in America.
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Ossining Public Library

Learn about the local history of Ossining when you take a trip to Ossining Public Library. Amble around the area's parks or visit its monuments.
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Nelson Park

Nelson Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants.
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Snowden Avenue Park

Snowden Avenue Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this quaint area or visit its top-notch restaurants.
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Frequently asked questions

How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from NZ$3,757 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.