Ossining Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Ossining Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Manhattan
Price was S$5,207, price is now S$3,934 per person
S$3,934
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (1,007 reviews)
The staff is amazing, especially Tommy and Chris. Super helpful and welcoming. Our room was spotless and beautiful in a city where things are not easily kept that way.

Reviewed on 7 Nov, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was S$8,772, price is now S$5,526 per person
S$5,526
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was S$5,648, price is now S$4,096 per person
S$4,096
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (4,191 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Save 100% on your flight
Price was S$16,822, price is now S$12,342 per person
S$12,342
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on 6 Nov, 2026

The Merchant Hotel Lower East Side

The Merchant Hotel Lower East Side

4 out of 5
Manhattan
Price was S$5,257, price is now S$3,966 per person
S$3,966
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (600 reviews)
Nice size room for the king.

Reviewed on 8 Nov, 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 S$222 per night from 15 Nov to 16 Nov
S$222
15 Nov - 16 Nov
includes taxes & fees
8.6/10 Excellent! (283 reviews)
"An amazing experience for us all-around..........Thank You. We'll see You again."

Reviewed on 4 Nov, 2026

Windrose On Hudson
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
The price is S$166 per night from 11 Nov to 12 Nov
S$166
11 Nov - 12 Nov
includes taxes & fees
7.2/10 Good! (1,250 reviews)
"It was very nice to stay there I slept like a baby till next time"

Reviewed on 10 Nov, 2026

LIV Hotel Bronx - Newly Built
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is S$294 per night from 19 Nov to 20 Nov
S$294
19 Nov - 20 Nov
includes taxes & fees
Tarrytown House Estate
See all 1,232 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 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.
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 S$3,934 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.