Ossining Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Ossining Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel 1080 Brooklyn

Hotel 1080 Brooklyn

3 out of 5
per person
23 Apr - 28 Apr
found 11 hours ago
Return flight included
London (LON) to New York (JFK)
7.8/10 Good! (27 reviews)
The noise of the train

Reviewed on 14 Feb,2025

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
23 Apr - 28 Apr
found 11 hours ago
Return flight included
London (LON) to New York (JFK)
9/10 Wonderful! (1,311 reviews)
Great location, easy to get to and from.

Reviewed on 17 Feb,2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
per person
23 Apr - 28 Apr
found 11 hours ago
Return flight included
London (LON) to New York (JFK)
8.6/10 Excellent! (5,578 reviews)
It was close to theatres and subway. It’s cute and clean. There was a strong chemical smell in our room which didn’t go away. Nothing fancy but clean and safe. Breakfast was not included as indicated on Expedia.

Reviewed on 18 Feb,2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
23 Apr - 28 Apr
found 11 hours ago
Return flight included
London (LON) to New York (JFK)
7.8/10 Good! (1,328 reviews)
It’s was good the only thing was the hot water when out in the hotel for a couple off hours

Reviewed on 18 Feb,2025

The Flat NYC

The Flat NYC

2 out of 5
Manhattan
per person
23 Apr - 28 Apr
found 11 hours ago
Return flight included
London (LON) to New York (JFK)
8.6/10 Excellent! (457 reviews)
Budget option. Very small rooms and loud from the outside. You can hear everybody. Showers are alright but wear shower shoes if you don't have a private shower.

Reviewed on 18 Feb,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 S$80 per night from 22 Mar to 23 Mar
S$80
includes taxes & fees
22 Mar - 23 Mar
6/10 (1,814 reviews)
"Great time"

Reviewed on 9 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 S$155 per night from 4 Mar to 5 Mar
S$155
includes taxes & fees
4 Mar - 5 Mar
8.2/10 Very Good! (1,988 reviews)
"Excellent customer service. Thanks Eileen for your attentions"

Reviewed on 17 Feb,2025

Royal Regency Hotel
Ramada by Wyndham Bronx
Ramada by Wyndham Bronx
3 out of 5
1000 Baychester Ave, Bronx, NY
Fully refundableReserve now, pay when you stay
The price is S$213 per night from 9 Mar to 10 Mar
S$213
includes taxes & fees
9 Mar - 10 Mar
8/10 Very Good! (1,010 reviews)
"Nice clean and comfortable"

Reviewed on 15 Feb,2025

Ramada by Wyndham Bronx
See all 1,108 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 S$1,251 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.