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Our top choices for Ossining hotels

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.2 out of 10, Very Good, (104)
"Clean room, staff were very welcoming"
United States
Semaj
$197 nightly
The price is $220
Jan 4 - Jan 5, 2026
Total with taxes and fees
Windrose On Hudson

Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
Ossining
$777 nightly
The price is $865
Jan 5 - Jan 6, 2026
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow

Marriott Park Ridge

Marriott Park Ridge
3.5 star property
Park Ridge
8.8 out of 10, Excellent, (873)
"Great hotel"
United States
Christopher
$143 nightly
The price is $164
Jan 1 - Jan 2, 2026
Total with taxes and fees
Marriott Park Ridge

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG
2.5 star property
Peekskill
9.2 out of 10, Wonderful, (1001)
"I highly recommend this hotel. "
United States
Leigh
$119 nightly
The price is $136
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1004)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
$101 nightly
The price is $115
Jan 4 - Jan 5, 2026
Total with taxes and fees
Overlook Lodge at Bear Mountain

Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY
3.0 star property
Dobbs Ferry
8.4 out of 10, Very Good, (1005)
"I love the hotel, and I enjoyed my stay. Clean room and friendly staff."
United States
Leonor
$106 nightly
The price is $122
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hilton Garden Inn Westchester Dobbs Ferry, NY

Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury
4.0 star property
Danbury
9.2 out of 10, Wonderful, (1004)
"Met and exceeded the expectations for my family's stay over the Christmas holiday. "
United States
Meagan
$155 nightly
The price is $179
Jan 18 - Jan 19, 2026
Total with taxes and fees
Hotel Zero Degrees Danbury

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1009)
"Clean room, friendly staff, good breakfast"
United States
Zuriber
$103 nightly
The price is $119
Jan 11 - Jan 12, 2026
Total with taxes and fees
DoubleTree by Hilton Hotel Nanuet

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
Nyack
8.6 out of 10, Excellent, (1008)
"Clean room , staff and amenities were all great"
United States
Elzie
$159 nightly
The price is $182
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hotel Nyack, a JdV by Hyatt Hotel

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (673)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
$170 nightly
The price is $193
Dec 29 - Dec 30
Total with taxes and fees
The Thayer Hotel at West Point

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1003)
"yes but the beds were not comfortable"
United States
Gene
$89 nightly
The price is $102
Jan 4 - Jan 5, 2026
Total with taxes and fees
Inn on the Hudson

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
2.5 star property
Elmsford
8.2 out of 10, Very Good, (1464)
"Room was clean and cozy, staff was very friendly and professional. "
United States
Jose Luis
$116 nightly
The price is $133
Jan 4 - Jan 5, 2026
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (663)
"Clean room and so close to West Point!! Great experience 👍 "
United States
SHANNON
$100 nightly
The price is $113
Jan 11 - Jan 12, 2026
Total with taxes and fees
West Point Motel

Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG
2.5 star property
Fort Montgomery
9.2 out of 10, Wonderful, (217)
"Breakfast was great!"
United States
Todd
$116 nightly
The price is $131
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express West Point by IHG

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1019)
"Great stay and room was very nice"
United States
Emmanuel
$98 nightly
The price is $120
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn Harriman Woodbury

Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County
3.0 star property
Tarrytown
9.0 out of 10, Wonderful, (1002)
"Nice clean place.. friendly staff .. fireplace in lobby perfect for chillin "
United States
Adam
$161 nightly
The price is $184
Jan 4 - Jan 5, 2026
Total with taxes and fees
Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Stamford Downtown

Courtyard by Marriott Stamford Downtown
3.0 star property
Downtown Stamford
9.0 out of 10, Wonderful, (841)
"Super attentive staff and very welcoming! Clean and moderately quiet for its central location!"
United States
TIFFANI
$215 nightly
The price is $247
Jan 4 - Jan 5, 2026
Total with taxes and fees
Courtyard by Marriott Stamford Downtown

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
Tarrytown
8.2 out of 10, Very Good, (1003)
"It was a lovely stay. The room was really comfortable and quiet "
United States
Kathy
$171 nightly
The price is $196
Jan 18 - Jan 19, 2026
Total with taxes and fees
Tarrytown House Estate

SpringHill Suites by Marriott Tarrytown Westchester County

SpringHill Suites by Marriott Tarrytown Westchester County
3.0 star property
Tarrytown
8.4 out of 10, Very Good, (1000)
"Room was clean and great size."
Canada
Robert
$152 nightly
The price is $174
Jan 4 - Jan 5, 2026
Total with taxes and fees
SpringHill Suites by Marriott Tarrytown Westchester County

Hyatt Place New York/Yonkers

Hyatt Place New York/Yonkers
3.0 star property
Southeast Yonkers
9.0 out of 10, Wonderful, (1314)
"We loved our stay! Clean room, good breakfast and the complimentary parking was a plus! Will definitely stay again!"
United States
Sandra
$127 nightly
The price is $153
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hyatt Place New York/Yonkers
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Stay near popular Ossining attractions

Learn more about Ossining

Sing Sing Prison Museum offers a fascinating glimpse into America's most notorious correctional facility, with guided tours by former officers. Hike the scenic Old Croton Aqueduct Trail and then grab lunch at one of the diverse restaurants along the Hudson River waterfront.

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

Top Ossining Hotel Reviews

More cheap stays in Ossining

Hotels in Ossining with star-rating

Find out more about Ossining

Top reasons to visit Ossining

  • Scenic Outdoor Activities: Enjoy picturesque paths, urban parks, and nature preserves perfect for relaxation and adventure.
  • Family-Friendly Attractions: Explore various activities suitable for families, ensuring fun for all ages.
  • Charming Local Shopping: Discover unique local shops and boutiques that add to the vibrant community atmosphere.
  • Diverse Accommodation Options: Choose from cozy bed and breakfasts to hotels, catering to various preferences and needs.
  • Nearby Skiing Opportunities: Experience skiing at nearby ski fields for a thrilling winter adventure.

Find great hotels near Ossining

Ossining, New York, offers a diverse array of accommodation options, from cozy bed and breakfasts to well-equipped hotels. Whether you seek a business-friendly environment, pet-friendly amenities, or an LGBTQIA-welcoming atmosphere, this charming town has something for everyone. Explore the best hotels and available options to ensure a comfortable stay while enjoying the unique charm and beauty of Ossining.

  • Ramada by Wyndham Rochelle Park Near Paramus: Located 21 miles from Ossining, this hotel is perfect for those seeking comfort and convenience. With a variety of dining options including a bar, restaurant, and complimentary breakfast, it caters to both leisure and business travelers. Guests can unwind with amenities such as premium TV channels and cable TV in their rooms. For those looking to stay active, fitness facilities are available on-site. Plus, the nearby metro station and shopping district make it easy to explore the local area.
  • Amsterdam Hotel: Situated 19 miles from Ossining, the Amsterdam Hotel is designed for business travelers seeking a professional atmosphere. This property offers essential business amenities such as a business center and multiple meeting rooms, making it an ideal choice for corporate events. Its proximity to the business district ensures guests have easy access to important offices and services, all while providing a comfortable stay to recharge after a busy day.
  • Baymont by Wyndham White Plains - Elmsford: Just 7 miles from Ossining, the Baymont by Wyndham White Plains - Elmsford is a family-friendly hotel that also caters to business needs. With accessible business facilities, including a 24-hour business center and meeting rooms, it ensures that both leisure and corporate guests are well taken care of. Families will appreciate amenities such as free cribs and first aid kits, making it a safe and convenient choice for travelers with children. The inviting atmosphere and thoughtful services promise a delightful stay.

Where to stay in and around Ossining

Ossining, New York, offers a delightful blend of outdoor activities and family-friendly experiences. Nestled near downtown, you can explore lovely green spaces and enjoy a cozy getaway atmosphere. Nearby cities provide a romantic and relaxing vibe, perfect for those looking to unwind. With friendly locals and a vibrant city center, Ossining is an ideal destination for travelers seeking both adventure and tranquility on their vacation.

  • Crotonville: Nestled within the Ossining area, Crotonville is a charming village that offers a blend of cultural and outdoor experiences. With its peak visitor months in April to May and December, this locale draws families and culture enthusiasts alike. The village boasts convenient access to shopping centers and educational venues, making it ideal for family outings. Explore the rich history through its historic buildings and sites, where you can immerse yourself in the local heritage while enjoying a pleasant day out.
  • Maryknoll: Located a mere 2 miles from Ossining, Maryknoll is a vibrant city that thrives on outdoor and family-friendly activities. Summer months, particularly July and August, see a rise in visitors eager to partake in sports such as baseball and soccer. The city is home to beautiful urban parks and event venues that host a variety of activities throughout the year. Whether you’re looking to enjoy a picnic in the park or catch a local sports game, Maryknoll's energetic atmosphere provides a perfect backdrop for a memorable vacation.
  • Briarcliff Manor: Just 2 miles from Ossining, Briarcliff Manor is a picturesque city that offers a delightful mix of outdoor adventures and cultural experiences. With visitor peaks in January and during the spring months, this area is great for families looking to explore. The local shopping areas and educational venues cater to diverse interests, while attractions such as lakes and historic houses provide a scenic and enriching experience. Whether hiking, shopping, or enjoying the tranquil lakeside, Briarcliff Manor invites you to create lasting memories.

Things to do near Ossining

Ossining offers a perfect blend of outdoor and family-friendly activities, making it an ideal vacation spot. Visitors can enjoy scenic strolls along picturesque paths, explore local shopping areas, and partake in skiing at nearby ski fields. Whether you're looking for a relaxing day outdoors or some fun shopping experiences, Ossining has something for everyone to enjoy.

Shopping

In Ossining, you can visit Rockland Bakery, located 8 miles away, known for its delicious baked goods. If you're up for a drive, check out Westchester's Ridge Hill, located 14 miles away, offering a variety of shops and family-friendly atmosphere. Woodbury Common Premium Outlets is 17 miles away, featuring numerous brand outlets.

Recreation

Experience the vibrant ambiance of Tarrytown Music Hall, just 6 miles from Ossining, where engaging performances uplift your spirit. Enjoy tranquility at Hardscrabble Wilderness Area, located 3 miles away, perfect for relaxation amidst nature. For sports enthusiasts, Rockland Lake State Park Championship Golf Course offers outdoor fun, also 3 miles from Ossining.

Adventure

Experience thrilling outdoor fun at Palisades Climb Adventure, a zipline ropes course located 7 miles from Ossining. Enjoy high-speed excitement at Grand Prix New York, an exhilarating karting venue 8 miles away. For a more tranquil adventure, explore the scenic Orange Trailhead, 7 miles from town.

Nightlife

Experience a night of culture and romance at the Westchester Broadway Theatre, only 7 miles away. For some adventure, visit Lucky Strike, an exciting arcadeAdventureZone, also 7 miles out. If you're in the mood for a movie, Maritime IMAX offers entertainment and romance vibes just 24 miles away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Ossining

To save money on your trip to Ossining, plan your visit between January and March for lower accommodation rates. Book hotels about a month in advance or explore last-minute deals on Expedia. Sundays are typically the cheapest days to stay, while Saturdays are the most expensive. Utilize Expedia's search tool to compare prices and filter by budget or eco-friendly options. Consider bundling your hotel with flights and activities for further savings, and join the One Key membership for exclusive discounts and cash back on future bookings.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Ossining are January to March, where the prices are slightly lower. This is in comparison to September to October and December, where prices are slightly higher.
  • The best time to book a hotel: Booking a hotel in Ossining about 1 month out from when you are planning to stay is usually when prices are lowest. If you're a little more spontaneous, you could also peruse Expedia's last minute deals for hotels, look out for the green banner below the price, as this indicates a cheaper deal.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Ossining is Sunday. The most expensive day to stay in Ossining is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool lets you customize your travel preferences by choosing your budget, desired location, and additional criteria. You can easily arrange the results from the lowest to the highest prices, ensuring you find the most affordable hotels first. Additionally, you have the option to narrow your search by hotel type; for instance, selecting the Eco-certified filter will display sustainable and environmentally-friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your Ossining hotel reservation with your flights and activities through an Expedia package.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in and around Ossining

Ossining, New York, offers a delightful mix of outdoor and family-friendly activities, making it perfect for city-themed vacations. Visitors can explore urban parks, nature preserves, and modern colleges and universities. These attractions provide a rich blend of cultural experiences and recreational opportunities, catering to travelers seeking both adventure and family bonding in a vibrant setting.

  • Van Cortlandt Manor: Explore this beautifully restored historic house, showcasing 18th-century architecture and stunning gardens. The manor offers a glimpse into the lives of early American settlers and hosts various cultural events throughout the year.
  • Sing Sing Correctional Facility: Discover the history of this infamous prison through guided tours that delve into its notable past and the justice system. The facility has housed many notorious criminals and offers a unique perspective on American penal history.
  • Croton Point Park: Enjoy a family-friendly urban park featuring scenic views of the Hudson River. With picnic areas, walking trails, and recreational amenities, it’s a perfect spot for outdoor activities and relaxation in nature.

Best time to go to Ossining

The best time to visit Ossining can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Ossining falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Ossining falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.0°F (-1.1°C)Light RainMostly SunnySlightly LowSlightly Low
February31.6°F (-0.2°C)Light RainMostly SunnySlightly LowSlightly Low
March38.8°F (3.8°C)Light RainMostly SunnyAverageSlightly Low
April49.8°F (9.9°C)Light RainMostly SunnySlightly HighAverage
May60.1°F (15.6°C)Light RainMostly SunnyAverageAverage
June68.9°F (20.5°C)Light RainMostly SunnyAverageAverage
July75.6°F (24.2°C)Light RainMostly SunnySlightly HighAverage
August73.9°F (23.3°C)Light RainMostly SunnyAverageAverage
September66.9°F (19.4°C)Light RainMostly SunnySlightly HighSlightly High
October56.1°F (13.4°C)Light RainMostly SunnyAverageSlightly High
November44.2°F (6.8°C)Light RainMostly SunnyAverageAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowSlightly High

The nearest major airports for your trip to Ossining

Traveling to Ossining, New York, is convenient with several major airports nearby. John F. Kennedy International Airport (JFK) is 36 miles away, with excellent hotel options like the 5-star Arlo Williamsburg, The William Vale, and the 4.5-star Boro Hotel, each located 11 miles from the airport. Newark Liberty International Airport (EWR) is 37 miles from Ossining, featuring luxurious stays at The Dominick, The Wall Street Hotel, and The Beekman, all just 9 miles away. Lastly, LaGuardia Airport (LGA) is 27 miles from Ossining, close to 5-star hotels like Virgin Hotels New York City, The Mark, and The Carlyle, each within 6 to 5 miles of the airport.

Frequently asked questions

When is the best time to go to Ossining?
The most popular time to visit Ossining is in the fall, particularly during September and October. During these months, the weather is pleasantly crisp, with temperatures typically ranging from the mid-50s to mid-70s Fahrenheit, making it superb for outdoor activities and leisurely strolls along the Hudson River waterfront.

As you plan your visit, keep in mind that while the peak tourist activity occurs during the warmer months, the fall offers a unique charm with vibrant foliage that enhances the natural beauty of Ossining. Scenic drives and hikes in nearby parks, such as Croton Point Park, become breathtaking as the leaves change color, inviting you to immerse yourself in the stunning landscape.

Additionally, September and October are fantastic for those who appreciate cultural experiences. The local community often hosts farmers' markets, art fairs, and seasonal festivals, allowing visitors to engage with the area's rich heritage and craft. This creates a wonderful opportunity to savor local flavors and crafts, all while enjoying the comfortable weather.

If you're looking for a more budget-friendly option, consider visiting in late November or early December. This time can be less crowded, and you'll find that accommodations and activities may be more affordable, allowing you to experience Ossining's charm without the peak season prices.
Where can I find the best nightlife in Ossining?
Ossining, New York, offers a charming small-town atmosphere, but when it comes to nightlife, it's more subdued compared to larger urban areas.

For those seeking evening activities, the downtown area features a few cozy bars and restaurants where you can enjoy a casual dinner and drinks. Establishments like The Boathouse offer a lovely riverside setting, superb for unwinding with friends while enjoying scenic views of the Hudson River.

If you're willing to venture a bit further, nearby towns like Sleepy Hollow and Tarrytown boast a more vibrant nightlife scene, with options ranging from lively pubs to intimate wine bars. These areas provide a nice variety of places to explore, ensuring a relaxed yet enjoyable night out.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Ossining hotel for you.
How can I save on a Ossining hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Ossining hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Ossining hotel?
Prices for hotels in Ossining often vary, but you can find a great deal from $118 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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