Ossining Trip

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    Better together
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Top hotels in Ossining

Baymont by Wyndham White Plains - Elmsford
Baymont by Wyndham White Plains - Elmsford
2.5 out of 5
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is ₹11,554 per night from 29 Jun to 30 Jun
₹11,554
₹13,214 total
29 Jun - 30 Jun
includes taxes & fees
8.2/10 Very Good! (1,362 reviews)
"Convenient stay for an overnight trip. Close proximity to the highway. Could hear noise through the doors and weirdly in the bathroom vent, other than that, a decent stay."

Reviewed on 27 Jun 2025

Baymont by Wyndham White Plains - Elmsford
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,593 reviews)
"This property is like stepping back in time, but it’s clean and well taken care of. (Minus the very dirty chandelier outside of the elevators.) the fake flowers in the room should probably hit the road. They are outdated and just fancy dust collectors. The outlets did not keep cords plugged in. The ..."

Reviewed on 26 Jun 2025

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Amsterdam Hotel
Hilltop Inn & Suites
Hilltop Inn & Suites
2.5 out of 5
125 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is ₹8,497 per night from 29 Jun to 30 Jun
₹8,497
₹10,006 total
29 Jun - 30 Jun
includes taxes & fees
6.8/10 (244 reviews)
"Quiet...accessible....generous parking Worth the price"

Reviewed on 24 Jun 2025

Hilltop Inn & Suites
See all 1,201 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 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.

Popular places to visit

Depot Square

Explore the great outdoors at Depot Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this family-friendly area.

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