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Hotels in Ossining

Q: What accommodations do travelers recommend in Ossining?

Guests like Windrose On Hudson , Armoni Inn & Suites and Baymont by Wyndham White Plains - Elmsford .

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Dates

June 2026

July 2026

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Where to stay in Ossining?

Windrose On Hudson

Ossining

CNY1,301 total

includes taxes & fees

May 24 - May 25

Ossining Vacation Rental Near River, Trails & Mta!

Ossining

CNY5,856 total

includes taxes & fees

May 31 - Jun 1

Westchester Summer Pool Pet Friendly Events Games

Ossining

CNY9,284 total

includes taxes & fees

May 20 - May 21

Red Carpet Inn

Cove - East Side - Shippan

CNY704 total

includes taxes & fees

May 24 - May 25

Amsterdam Hotel

Downtown Stamford

CNY821 total

includes taxes & fees

May 31 - Jun 1

The Stamford Hotel

Downtown Stamford

CNY1,192 total

includes taxes & fees

May 25 - May 26

Stamford Marriott Hotel & Spa

Downtown Stamford

CNY1,791 total

includes taxes & fees

May 24 - May 25

Residence Inn Stamford Downtown

Downtown Stamford

CNY2,029 total

includes taxes & fees

Jun 5 - Jun 6

Courtyard by Marriott Stamford Downtown

Downtown Stamford

CNY1,739 total

includes taxes & fees

Jun 7 - Jun 8

The Lloyd Stamford, Tapestry Collection by Hilton

Downtown Stamford

CNY1,343 total

includes taxes & fees

Jun 7 - Jun 8

Hampton Inn & Suites Stamford

West Side

CNY1,360 total

includes taxes & fees

Jun 7 - Jun 8

DoubleTree by Hilton Stamford

Waterside

CNY1,122 total

includes taxes & fees

May 25 - May 26

The Armon Stamford Hotel & Conference

Ridgeway-Bullshead

CNY1,260 total

includes taxes & fees

May 31 - Jun 1

Super 8 by Wyndham Stamford/New York City Area

West Side

CNY791 total

includes taxes & fees

May 31 - Jun 1

Room, 2 Queen Beds, Accessible (Mobility/Hearing Impaired Accessible) | Premium bedding, desk, blackout drapes, iron/ironing board

La Quinta Inn & Suites by Wyndham Stamford / New York City

Waterside

CNY729 total

includes taxes & fees

Jun 7 - Jun 8

Hyatt Regency Greenwich

Old Greenwich

CNY1,455 total

includes taxes & fees

Jun 7 - Jun 8

Ethan Allen Hotel

Danbury

CNY908 total

includes taxes & fees

May 25 - May 26

Residence Inn Marriott Danbury

Danbury

CNY1,168 total

includes taxes & fees

Jun 7 - Jun 8

J House Greenwich

Riverside

CNY2,182 total

includes taxes & fees

May 25 - May 26

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Danbury

CNY1,056 total

includes taxes & fees

May 25 - May 26

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Go beyond your typical stay in Ossining

Apartment

Spa

Top landmarks in Ossining

Travelers Rest

If you're looking for things to do when staying in Ossining, go to Travelers Rest.

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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

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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Check out reviews of Ossining hotels guests love

Baymont by Wyndham White Plains - Elmsford

6/10 Okay

"Breakfast was very limited"

La Quinta Inn & Suites by Wyndham Stamford / New York City

6/10 Okay

"The hotel had many areas of maintentance going on and not well cleaned. Also the elevator wasn't working. I was on 5th fl. There was no maage on site to help gv explanation it was not working during the night or mring. No recompense either."

Hotel Nyack, a JdV by Hyatt Hotel

6/10 Okay

"This hotel has the most uncomfortable setup I have ever experienced. I was here for an event I was hosting and figured spending the night would be convenient. I was wrong, the first night I got ZERO sleep. There was a constant knocking sound in our room, it was brutal. I felt like I was sleeping in a shipping container. Just not very cozy. "

Hilltop Inn & Suites

4/10 Poor

"first day the room smelled like cigs. No body wash in the bathroom, but there is lotion & shampoo. Microwave & fridge were a plus. For a queen bed it was pretty small. Breakfast is bread, cereals & donuts. Parking was a big plus though, big. Outdoor pool was nice, of course when it gets warmer it’s open."

Hampton Inn & Suites Yonkers

8/10 Good

"It was good. I would stay here again. The only problem is that some of the pillows have down/goose feathers in them and I am HIGHLY allergic, so navigating that was a bit tricky. There was no one in housekeeping that evening and I couldn't leave the pillows in the room and the front desk couldn't help us. Fortunately we were traveling with others and they were able to switch out pillows. If I hadn't caught this, I could've been hospitalized. I did expect the hotel to be more helpful in remedying the problem instead of leaving it up to us. But otherwise everyone was kind and helpful. It would also be nice if breakfast was available until 10am :)"

Frequently asked questions

How much does a hotel room cost in Ossining?

You can choose a great hotel in Ossining from CNY704 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:

Windrose On Hudson: A hotel with an average guest rating of 8.4 out of 10

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. Downtown Tarrytown is a central neighborhood for your Ossining vacation.

What accommodations do travelers recommend in Ossining?

Guests like Windrose On Hudson, Armoni Inn & Suites and Baymont by Wyndham White Plains - Elmsford.

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 8 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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