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Hotels in Ossining

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Check prices for these dates

Next weekend
May 22 - May 24
In two weeks
May 29 - May 31

Where to stay in Ossining?

Restaurant

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.4 out of 10, Very Good, (138 reviews)
Unwind at this Hudson River retreat with serene views. The cozy café offers breakfast while the fitness center keeps your routine intact. Near Van Cortlandt Manor and Croton Point Park, this hotel provides free WiFi and parking for easy Westchester exploration.
The price is $172
$191 total
includes taxes & fees
May 24 - May 25
Windrose On Hudson
House (5 Bedrooms) | Interior

Ossining Vacation Rental Near River, Trails & Mta!

Ossining Vacation Rental Near River, Trails & Mta!
3.0 star property
Ossining
Escape to this waterfront gem in Ossining with its own marina, where patios offer peaceful garden views. The fully-equipped kitchen and DVD player make family stays comfortable, while nearby historical society and parks await exploration.
The price is $287
$861 total
includes taxes & fees
May 20 - May 21
Ossining Vacation Rental Near River, Trails & Mta!
Villa | 5 bedrooms

Westchester Summer Pool Pet Friendly Events Games

Westchester Summer Pool Pet Friendly Events Games
2.0 star property
Ossining
The price is $775
$1,363 total
includes taxes & fees
May 18 - May 19
Westchester Summer Pool Pet Friendly Events Games
Restaurant

Red Carpet Inn

Red Carpet Inn
2.0 star property
Cove - East Side - Shippan
6.8 out of 10, (1,008 reviews)
Red Carpet Inn sits conveniently near Stamford's train station with easy access to Chelsea Piers and Cove Island Park. Enjoy complimentary WiFi and parking, plus 24-hour front desk service. Unwind with drinks at the bar or savor a meal at the on-site restaurant.
The price is $94
$108 total
includes taxes & fees
May 18 - May 19
Red Carpet Inn
Lobby

Amsterdam Hotel

Amsterdam Hotel
2.0 star property
Downtown Stamford
8.4 out of 10, Very Good, (1,753 reviews)
Escape to this serene hotel near Stamford's shopping and restaurants. With free WiFi, parking, and continental breakfast, you'll enjoy the fitness center and garden terrace. Guests consistently praise the helpful staff and peaceful atmosphere for a comfortable stay.
The price is $103
$119 total
includes taxes & fees
May 25 - May 26
Amsterdam Hotel
Lobby

The Stamford Hotel

The Stamford Hotel
3.5 star property
Downtown Stamford
7.8 out of 10, Good, (1,149 reviews)
Walk to restaurants and attractions from this centrally located hotel near Stamford Transportation Center. The fitness center keeps your routine on track, while 700 Main restaurant serves American cuisine throughout the day. The bar offers relaxation after exploring nearby Stamford Town Center.
The price is $161
$185 total
includes taxes & fees
May 25 - May 26
The Stamford Hotel
Front of property - evening/night

Stamford Marriott Hotel & Spa

Stamford Marriott Hotel & Spa
3.5 star property
Downtown Stamford
8.0 out of 10, Very Good, (1,001 reviews)
Escape to this Connecticut haven with a full-service spa offering massages and aromatherapy. Steps from Metro-North Station, you'll find Stamford Town Center and local arts venues nearby. Enjoy Sam's American Bistro, fitness center, and bar.
The price is $224
$258 total
includes taxes & fees
May 26 - May 27
Stamford Marriott Hotel & Spa
View from property

Residence Inn Stamford Downtown

Residence Inn Stamford Downtown
3.0 star property
Downtown Stamford
9.4 out of 10, Exceptional, (395 reviews)
This downtown Stamford hotel offers a refreshing indoor pool and complimentary breakfast to start your day. Catch the free beach shuttle or walk to the train station in minutes. The restaurant, bar, and 24-hour fitness center provide comfort while exploring nearby arts venues.
The price is $259
$298 total
includes taxes & fees
May 24 - May 25
Residence Inn Stamford Downtown
2 restaurants, American cuisine

Courtyard by Marriott Stamford Downtown

Courtyard by Marriott Stamford Downtown
3.0 star property
Downtown Stamford
9.0 out of 10, Wonderful, (865 reviews)
The price is $222
$255 total
includes taxes & fees
May 24 - May 25
Courtyard by Marriott Stamford Downtown
Restaurant

The Lloyd Stamford, Tapestry Collection by Hilton

The Lloyd Stamford, Tapestry Collection by Hilton
3.5 star property
Downtown Stamford
8.8 out of 10, Excellent, (491 reviews)
This boutique hotel combines contemporary style with convenience near the train station. After workouts in the 24-hour fitness center, unwind at the restaurant or bar/lounge. Museum of Black World War II History and Stamford Center for the Arts await nearby.
The price is $171
$197 total
includes taxes & fees
Jun 7 - Jun 8
The Lloyd Stamford, Tapestry Collection by Hilton
Bar (on property)

Hampton Inn & Suites Stamford

Hampton Inn & Suites Stamford
2.5 star property
West Side
8.6 out of 10, Excellent, (1,003 reviews)
Just steps from Stamford Transportation Center, this hotel offers free breakfast, WiFi, and parking. Work out in the fitness center, dine at the restaurant, or grab a drink at the bar. Museum of Black World War II History awaits nearby.
The price is $174
$200 total
includes taxes & fees
May 24 - May 25
Hampton Inn & Suites Stamford
Reception

DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford
3.5 star property
Waterside
7.4 out of 10, Good, (1,002 reviews)
Near Stamford Transportation Center, this hotel offers a refreshing indoor pool and 24-hour health club. Enjoy American cuisine at Tavola Restaurant or unwind at the bar. Stamford Center for the Arts and Town Center are just moments away.
The price is $143
$165 total
includes taxes & fees
May 24 - May 25
DoubleTree by Hilton Stamford
Garden view

The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference
2.5 star property
Ridgeway-Bullshead
7.8 out of 10, Good, (785 reviews)
Soak in the indoor pool or unwind in the hot tub after your workout at the 24-hour fitness center. Ricotta restaurant serves three daily meals, complementing your free breakfast and WiFi. Hand & Stone Massage is nearby for extra relaxation.
The price is $161
$185 total
includes taxes & fees
May 17 - May 18
The Armon Stamford Hotel & Conference
Exterior

Super 8 by Wyndham Stamford/New York City Area

Super 8 by Wyndham Stamford/New York City Area
2.5 star property
West Side
6.4 out of 10, (1,000 reviews)
Start your day with free breakfast before exploring nearby attractions like E. Gaynor Brennan Golf Course. This hotel offers complimentary WiFi and parking just minutes from Stamford Transportation Center, with friendly staff ready to enhance your stay.
The price is $101
$116 total
includes taxes & fees
May 19 - May 20
Super 8 by Wyndham Stamford/New York City Area
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

La Quinta Inn & Suites by Wyndham Stamford / New York City
3.0 star property
Waterside
6.8 out of 10, (1,327 reviews)
Just off the highway, this practical hotel offers a refreshing indoor pool and complimentary perks including breakfast, WiFi, and parking. City Limits restaurant serves 3 daily meals, while the attentive staff ensures a pleasant stay near E. Gaynor Brennan Golf Course.
The price is $93
$107 total
includes taxes & fees
Jun 7 - Jun 8
La Quinta Inn & Suites by Wyndham Stamford / New York City
Bar (on property)

Hyatt Regency Greenwich

Hyatt Regency Greenwich
4.0 star property
Old Greenwich
8.6 out of 10, Excellent, (1,005 reviews)
The price is $186
$214 total
includes taxes & fees
Jun 7 - Jun 8
Hyatt Regency Greenwich
Dinner served

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
8.0 out of 10, Very Good, (1,221 reviews)
Convenient to a train station, this hotel offers free WiFi and parking. Splash around in the seasonal outdoor pool, grab a drink at the bar, or exercise in the fitness center. Clean rooms with comfy beds await after exploring nearby Xtreme Play Adventure Park.
The price is $116
$134 total
includes taxes & fees
May 25 - May 26
Ethan Allen Hotel
Exterior

Residence Inn Marriott Danbury

Residence Inn Marriott Danbury
3.0 star property
Danbury
8.2 out of 10, Very Good, (376 reviews)
This Danbury hotel offers free breakfast, WiFi, and parking near Tarrywile Park and Mansion. Grab a bite at the restaurant after your workout. Business travelers appreciate the prime location and exceptional service from the attentive team.
The price is $148
$170 total
includes taxes & fees
Jun 7 - Jun 8
Residence Inn Marriott Danbury
Terrace/patio

J House Greenwich

J House Greenwich
4.0 star property
Riverside
9.0 out of 10, Wonderful, (1,014 reviews)
Immerse in a relaxing sanctuary near Riverside's train station. This Art Deco hotel features deep-tissue massages at the spa, Italian dining at Tony's, and a refreshing pool with its own bar. Free breakfast and parking enhance your Greenwich getaway.
The price is $246
$324 total
includes taxes & fees
May 27 - May 28
J House Greenwich
Exterior

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

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
2.5 star property
Danbury
9.2 out of 10, Wonderful, (366 reviews)
This business-friendly hotel offers an outdoor pool and fitness center just minutes from Jumpz Trampoline and Thrillz Adventure Park. Enjoy clean rooms with free WiFi, plus complimentary breakfast to start your day. The helpful staff ensures a comfortable stay.
The price is $131
$151 total
includes taxes & fees
May 17 - May 18
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
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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When is the best time to visit Ossining?

Our prices for hotels in Ossining are cheapest in December
Price trends for hotels in Ossining
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for Ossining
May
High 21°C / low 11°C. Sunny most days.
View properties in May
21°
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May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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26°
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June, no crowd data, average high temperature 26 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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29°
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July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
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28°
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August, no crowd data, average high temperature 28 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
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24°
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September, no crowd data, average high temperature 24 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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18°
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October, no crowd data, average high temperature 18 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
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11°
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November, no crowd data, average high temperature 11 degrees Celsius, average low temperature 3 degrees Celsius. Sunny most days.
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5°
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December, no crowd data, average high temperature 5 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
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January, no crowd data, average high temperature 2 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
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4°
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February, no crowd data, average high temperature 4 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
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8°
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March, no crowd data, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
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15°
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April, no crowd data, average high temperature 15 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
6°
Monthly weather averages (˚C)

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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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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Photo by louann ohora
Open Photo by louann ohora

Check out reviews of Ossining hotels guests love

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

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

2/10 Terrible
"This location is under construction and there were construction materials all over the place. Our room didn't have a shower curtain, had 1 pillow on the bed, and the carpet was damp throughout the room. If it hadn't been so late when we arrived, we would have not stayed here."
Jennifer R 1-night trip
Posted 3 hours ago
La Quinta Inn & Suites by Wyndham Stamford / New York City

Frequently asked questions

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.