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Hotels in Ossining

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Check prices for these dates

Tonight
Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Where to stay in Ossining?

Terrace/patio
Windrose On Hudson
Windrose On Hudson
3.0 star property
8.2 out of 10, Very Good, (104)
  • cleanliness
    Take in Hudson riverside scenes at this Ossining hotel with a fitness center.
The price is CNY1,174
CNY1,307 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Windrose On Hudson
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.
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Top landmarks in Ossining

Rest stop area beside interstate highway where travelers rest and sight see Tioga Reservoir and Dam in Pennsylvania New York state border

Travelers Rest

If you're looking for things to do when staying in Ossining, go to Travelers Rest.
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Lovely spot in Westchester, NY
Photo by louann ohora
Open Photo by louann ohora

Teatown Lake Reservation

If you'd like to get a taste of Ossining student life, check out Teatown Lake Reservation, located 3.8 mi (6.1 km) from central Ossining. Why not take a stroll along the riverfront and watch the sunset while you're here? Want to stretch your legs some more? Head to Croton Point Park and Brinton Brook Sanctuary, both nearby.
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Learn more about Ossining

Ossining is applauded for its cultural attractions such as Sing Sing Prison Museum and Ossining Historical Society.

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Main building at Maryknoll
Photo by louann ohora
Open Photo by louann ohora

Check out reviews of Ossining hotels guests love

Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

10/10 Excellent
"Great stay, really comfortable and had great night’s sleep. Only wish that room service were every day. Other than that, all were great!"
Joseph 3-night trip
Posted 2 days ago
Hampton Inn & Suites Yonkers

Frequently asked questions

How much does a hotel room cost in Ossining?
You can choose a great hotel in Ossining from CNY746 with properties to suit all budgets and needs. If you're looking for an affordable hotel in Ossining that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.
How can I find deals and earn rewards at Ossining hotels?
Discover great deals on Ossining hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Ossining hotels.
Can I book Ossining hotels with free cancellation?
In order to book a refundable Ossining hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". Many hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some of the best Ossining hotels with free parking?
If you're arriving by car, choosing a great Ossining hotel with free parking is a plus. Our travelers' favorites include:
What are some popular hotels in central Ossining?
For hotels in central Ossining, check out Hotel Nyack, a JdV by Hyatt Hotel and Windrose On Hudson. Travelers love Hotel Nyack, a JdV by Hyatt Hotel for its location, as well as the seasonal outdoor pool, hot tub and restaurant this hotel offers. Windrose On Hudson is another popular central hotel with a bar/lounge, a coffee shop/cafe and karaoke.
What accommodations do travelers recommend in Ossining?
Windrose On Hudson is an accommodation that is popular with guests.
Can I book refundable accommodations in Ossining?
If you need the flexibility to change your plans to Ossining, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Ossining if I want a vacation rental instead of a hotel?
Browse 6 vacation homes on our site.
What will the weather in Ossining be like during my trip?
The warmest months in Ossining are usually July and August with an average temp of 71°F. January and February are the chilliest months when the average temp is 34°F. The rainiest months are July and October.
Why should I book my Ossining accommodation with Hotels.com?
There are lots of reasons to book your Ossining trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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