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Hotels in Ossining

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Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

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 $197
$220 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 Ossining Dog Park, both nearby.
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Learn more about Ossining

Infamous Sing Sing Prison Museum offers a fascinating glimpse into America's most notorious correctional facility, where history feels eerily present. Louis Engel Waterfront Park provides a refreshing contrast with Hudson River views that make you forget what's just up the hill. The Ossining Historical Society reveals small-town America with unexpected depth and quirky artifacts. Teatown Lake Reservation offers trails where city stress evaporates among pristine forests surprisingly close to New York City. Depot Square buzzes with locals who've perfected small-town conversation while maintaining their metropolitan edge. The Thomas J. Watson Research Center stands as a modernist monument to big thinking in a village balancing prison history with cultural richness.

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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

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"Nice people and a nice clean and spacious room. Thank you "
Brett 1-night trip
Posted 12 hours ago
DoubleTree by Hilton Hotel Nanuet

Frequently asked questions

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.