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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, (109 reviews)
"Great staff"
United States
Timothy
$179 nightly
The price is $199
Feb 15 - Feb 16
Total with taxes and fees
Windrose On Hudson

NEW 45 Wolden Rd Ossining NY 10562

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
Ossining
$868 nightly
The price is $966
Mar 15 - Mar 16
Total with taxes and fees
NEW 45 Wolden Rd Ossining NY 10562

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, (1,123 reviews)
"Average Stay.. Was ok.. Lots of restaurants nearby.. Close to highway Staff was ok "
United States
Jaime
$88 nightly
The price is $101
Feb 22 - Feb 23
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Stamford / New York City

Red Carpet Inn

Red Carpet Inn
2.0 star property
Cove - East Side - Shippan
6.6 out of 10, (1,003 reviews)
"It was decent for a nights rest an hour away from the city. Not bad "
United States
Roxxanna
$80 nightly
The price is $93
Feb 23 - Feb 24
Total with taxes and fees
Red Carpet Inn

Amsterdam Hotel

Amsterdam Hotel
2.0 star property
Downtown Stamford
8.4 out of 10, Very Good, (1,739 reviews)
"Great Hotel"
United States
Debra
$103 nightly
The price is $119
Feb 17 - Feb 18
Total with taxes and fees
Amsterdam Hotel

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,000 reviews)
"The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price."
United States
Judith
$105 nightly
The price is $119
Feb 25 - Feb 26
Total with taxes and fees
Overlook Lodge at Bear Mountain

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
2.0 star property
Ardsley
8.6 out of 10, Excellent, (1,001 reviews)
"The rooms are renovated and modern, very comfortable beds. "
United States
Ravel
$95 nightly
The price is $109
Feb 16 - Feb 17
Total with taxes and fees
Ardsley Acres Hotel Westchester

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, (468 reviews)
"Very accommodating staff "
United States
Dutchie
$155 nightly
The price is $178
Mar 1 - Mar 2
Total with taxes and fees
The Lloyd Stamford, Tapestry Collection by Hilton

Courtyard by Marriott Stamford Downtown

Courtyard by Marriott Stamford Downtown
3.0 star property
Downtown Stamford
9.0 out of 10, Wonderful, (849 reviews)
"Great location, hotel was clean and modern Staff were great!"
United States
geraldine
$215 nightly
The price is $247
Feb 19 - Feb 20
Total with taxes and fees
Courtyard by Marriott Stamford Downtown

Super 8 by Wyndham Mahwah

Super 8 by Wyndham Mahwah
2.5 star property
Mahwah
7.4 out of 10, Good, (1,001 reviews)
"Room was very spacious and the staff was extremely helpful!!!!"
United States
Lydia
$79 nightly
The price is $91
Feb 15 - Feb 16
Total with taxes and fees
Super 8 by Wyndham Mahwah

Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah
3.0 star property
Mahwah
8.2 out of 10, Very Good, (1,002 reviews)
"Needs a fresh look and feel "
United States
Linda
$107 nightly
The price is $123
Feb 22 - Feb 23
Total with taxes and fees
Courtyard by Marriott Mahwah

The Stamford Hotel

The Stamford Hotel
3.5 star property
Downtown Stamford
7.8 out of 10, Good, (1,142 reviews)
"Not the highest standard rooms, but just what we needed: clean rooms, comfortable bed and friendly staff. "
United States
Anna
$142 nightly
The price is $164
Mar 15 - Mar 16
Total with taxes and fees
The Stamford Hotel

DoubleTree by Hilton Mahwah

DoubleTree by Hilton Mahwah
4.0 star property
Mahwah
7.8 out of 10, Good, (946 reviews)
"Great rate, restful sleep, and courteous staff. "
United States
Martin
$114 nightly
The price is $131
Feb 19 - Feb 20
Total with taxes and fees
DoubleTree by Hilton Mahwah

Residence Inn Stamford Downtown

Residence Inn Stamford Downtown
3.0 star property
Downtown Stamford
9.4 out of 10, Exceptional, (381 reviews)
"Great room and staff was great as well!"
United States
Amanda
$251 nightly
The price is $289
Feb 19 - Feb 20
Total with taxes and fees
Residence Inn Stamford Downtown

Hampton Inn & Suites Stamford

Hampton Inn & Suites Stamford
2.5 star property
West Side
8.6 out of 10, Excellent, (1,001 reviews)
"Staff is always friendly and helpfull."
United States
Christine
$161 nightly
The price is $185
Feb 15 - Feb 16
Total with taxes and fees
Hampton Inn & Suites Stamford

DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford
3.5 star property
Waterside
7.4 out of 10, Good, (1,000 reviews)
"Overall it was a good place to stay"
United States
Jacqueline
$141 nightly
The price is $162
Feb 22 - Feb 23
Total with taxes and fees
DoubleTree by Hilton Stamford

The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference
2.5 star property
Ridgeway-Bullshead
7.8 out of 10, Good, (732 reviews)
"I stayed here 2 days for work and it waa perfect. Quiet, clean, well sraffed. "
United States
Keith
$161 nightly
The price is $185
Mar 10 - Mar 11
Total with taxes and fees
The Armon Stamford Hotel & Conference

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1,001 reviews)
"The staff was really welcoming!"
United States
Devis
$89 nightly
The price is $102
Feb 15 - Feb 16
Total with taxes and fees
Inn on the Hudson

Marriott Park Ridge

Marriott Park Ridge
3.5 star property
Park Ridge
8.8 out of 10, Excellent, (899 reviews)
"Staff is always so pleasant ❤️"
United States
Roange Angie
$144 nightly
The price is $165
Feb 15 - Feb 16
Total with taxes and fees
Marriott Park Ridge

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)
"The hotel was affordable and suited our needs for our quick one night stopover. Staff was helpful, breakfast was good - we were happy with the experience."
United States
Peter
$77 nightly
The price is $88
Feb 22 - Feb 23
Total with taxes and fees
Super 8 by Wyndham Stamford/New York City Area
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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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

What is the best area to stay in Ossining?
The best area to stay in Ossining is near the waterfront, particularly around the Ossining Metro-North station and the adjacent village center.

This area offers convenient access to transportation and local amenities. It features a mix of historic buildings and renovated spaces, with restaurants and shops within easy walking distance. The waterfront itself includes parks and walking paths along the Hudson River. Couples appreciate this area for its scenic views and relaxed pace.

For solo travelers, staying near the train station provides excellent connectivity to New York City for day trips or business.
What are the best family hotels in Ossining?
For families visiting Ossining, the Windrose On Hudson is a highly recommended choice.

This 3-star hotel, with an 8.0 rating, offers a variety of features that are convenient for families, including free cribs, complimentary WiFi, and free self-parking. Guests can also make use of the fitness facilities. The hotel is located close to several points of interest, such as Van Cortlandt Manor, which is just 0.7 miles away, and Crawbuckie Park, 1.4 miles from the property. Find more child-friendly accommodations in Ossining
What are the best budget hotels in Ossining?
For a popular budget hotel in Ossining, the Windrose On Hudson is an excellent choice.

This 3-star hotel, with a solid 8.0 rating, offers a comfortable stay with valuable amenities such as free WiFi and complimentary self-parking. Guests also have access to fitness facilities, including an accessible fitness center. The hotel is conveniently located near local attractions like Van Cortlandt Manor, just 0.7 miles away, and Ossining Dog Park, which is 0.5 miles from the property. View all budget hotels in Ossining
When is the best time to go to Ossining?
The best time to visit Ossining is during the spring and fall months, specifically from April to June and September to October, when the weather is most pleasant for exploring the area.

During the spring, the Hudson Valley comes alive with blooming flowers and lush greenery, making it ideal for outdoor activities like hiking along the Old Croton Aqueduct Trail or visiting local parks. Temperatures are mild, typically ranging from the 50s to 70s Fahrenheit, which is comfortable for walking tours or enjoying a meal outdoors. This season is particularly appealing for couples looking for scenic strolls and relaxed dining experiences.

The fall offers cooler temperatures and stunning foliage, with the hillsides ablaze in reds, oranges, and yellows. This period is great for scenic drives along the Hudson River or exploring the local farms and orchards. Many local festivals and events also take place in the fall, adding to the area's appeal.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Ossining.
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 $91 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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