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Hotels in Ossining

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April 2026

2

May 2026

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Where to stay in Ossining?

Windrose On Hudson

Ossining

Take in Hudson riverside scenes at this Ossining hotel with a fitness center.

CNY1,790 total

includes taxes & fees

Apr 5 - Apr 6

Westchester Summer Pool Pet Friendly Events Games

Ossining

CNY7,207 total

includes taxes & fees

Apr 7 - Apr 8

Red Carpet Inn

Cove - East Side - Shippan

Wake to spacious, comfortable rooms near Stamford's transportation hub.

CNY562 total

includes taxes & fees

Apr 10 - Apr 11

Amsterdam Hotel

Downtown Stamford

Experience the quietest retreat close to Stamford Town Center and train station.

CNY799 total

includes taxes & fees

Apr 5 - Apr 6

The Stamford Hotel

Downtown Stamford

Explore downtown Stamford from this centrally located hotel near the train station.

CNY1,146 total

includes taxes & fees

Apr 8 - Apr 9

Stamford Marriott Hotel & Spa

Downtown Stamford

Convenient Stamford hotel close to metro station with relaxing on-site spa.

CNY1,543 total

includes taxes & fees

Apr 5 - Apr 6

Residence Inn Stamford Downtown

Downtown Stamford

Convenient train station access with indoor pool and free breakfast in Stamford.

CNY2,054 total

includes taxes & fees

Apr 12 - Apr 13

Courtyard by Marriott Stamford Downtown

Downtown Stamford

CNY1,760 total

includes taxes & fees

Apr 12 - Apr 13

The Lloyd Stamford, Tapestry Collection by Hilton

Downtown Stamford

Enjoy stylish accommodations steps from Stamford Transportation Center.

CNY1,333 total

includes taxes & fees

Apr 26 - Apr 27

Hampton Inn & Suites Stamford

West Side

Experience Stamford with easy train access, fitness center, and a welcoming bar.

CNY1,306 total

includes taxes & fees

Apr 12 - Apr 13

DoubleTree by Hilton Stamford

Waterside

Convenient train-station hotel with indoor pool for business or city exploration.

CNY1,177 total

includes taxes & fees

Apr 16 - Apr 17

The Armon Stamford Hotel & Conference

Ridgeway-Bullshead

Modern pool and fitness hotel in Stamford with conference center access.

CNY1,277 total

includes taxes & fees

Apr 12 - Apr 13

Super 8 by Wyndham Stamford/New York City Area

West Side

Enjoy convenient train access and daily amenities at this relaxed Stamford hotel.

CNY701 total

includes taxes & fees

Apr 19 - Apr 20

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

Interstate access and convenient Stamford location with an indoor pool year-round.

CNY708 total

includes taxes & fees

Apr 26 - Apr 27

Hyatt Regency Greenwich

Old Greenwich

CNY1,476 total

includes taxes & fees

Apr 3 - Apr 4

Ethan Allen Hotel

Danbury

Stay near Danbury Fair Mall with comfortable beds and seasonal poolside lounging.

CNY937 total

includes taxes & fees

Apr 9 - Apr 10

Residence Inn Marriott Danbury

Danbury

Unwind minutes from Danbury Fair Mall with a fitness center and helpful staff.

CNY992 total

includes taxes & fees

Apr 19 - Apr 20

J House Greenwich

Riverside

Boutique Art Deco retreat with spa indulgences and Italian cuisine by the station.

CNY2,222 total

includes taxes & fees

Apr 5 - Apr 6

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

Danbury

Experience poolside relaxation near popular Danbury attractions and Jumpz Trampoline.

CNY1,070 total

includes taxes & fees

Apr 5 - Apr 6

Springhill Suites By Marriott - Danbury

Danbury

CNY848 total

includes taxes & fees

Apr 9 - Apr 10

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Go beyond your typical stay in Ossining

Spa

Apartment

Top landmarks in Ossining

Travelers Rest

This historic restaurant, once a 19th-century stagecoach stop, serves American and German cuisine in elegant rooms with fireplaces. Explore the landscaped gardens with pond and waterfall before or after your meal.

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Teatown Lake Reservation

Explore 15 miles of trails across Teatown's 1,000-acre preserve featuring forests, lakes, and wetlands. The floating boardwalk provides excellent wildlife viewing and access to the island's native wildflowers.

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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

Hampton Inn White Plains/Tarrytown

6/10 Okay

"Did not eat the breakfast"

Ramada by Wyndham Bronx

6/10 Okay

"The mattresses are horrible but the overnight clerk or manager was nice enough to make some accommodations for us. The mattresses not being properly maintained is def a bummer. Pillows should be upgraded. Vending machines and arm should be upgraded and a larger variety of drinks should be available as well. Energy drinks at 7$ is not appropriate. A can of soda for 4 is ridiculous. Having someone watch you eat breakfast or make you your waffle just so you don’t make a mess is too much micro managing makes me feel like I’m being watched. To rooms wout jacuzzi’s are nice wifi nothing to be happy about "

LIV Hotel Bronx - Newly Built

4/10 Poor

"The only good thing was the parking lot, other than that.. as soon as you walk in you smell cigarettes, the lobby was not clean and you probably going to have to make a line.The smell in the elevator and the rooms is terrible!! I couldn't stay there not even for one night, the mattress was really hard, not comfortable at all. "

DoubleTree by Hilton Hotel Nanuet

2/10 Terrible

"Breakfast was mediocre, hot chocolate was cold had to ask them to reheat. Iron in the room didnt work, thermostat wasnt working in room. Hot tub was hot pool was nice n warm. Cleaning lady dian acted like the hotel towels were hers when i refused room service and jus said i needed new towels she was very disgruntled. "

Hyatt Place New York/Yonkers

10/10 Excellent

"Noelle and the staff were outstanding, but this definitely serves as a highlight to Noellle. Her warmth and knowledge was admirable and made my stay feel special! I could not have had such an amazing trip without her! Please give her a raise !!! Now- As far as the hotel, soooo clean, the breakfast bar was also very clean and well staffed with amazing options. I wish I would have gotten the name of the worker at the breakfast bar (starts with P); such a wonder soul to encounter! So helpful! Now- The rooms itself, are beautiful maintained with nice views of the area. First time staying someplace and not having to ask for anything! The room was very well prepped."

Frequently asked questions

How much does a hotel room cost in Ossining?

You can choose a great hotel in Ossining from CNY562 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?

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 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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