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Our top choices for Ossining hotels

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.4 out of 10, Very good, (137 reviews)
"Very pleasant stay. "
United States
Beth
The price is CA $227
CA $253 total
includes taxes & fees
May 24 - May 25
Windrose On Hudson

Westchester Summer Pool Pet Friendly Events Games

Westchester Summer Pool Pet Friendly Events Games
2.0 star property
Ossining
The price is CA $1,063
CA $1,869 total
includes taxes & fees
May 19 - May 20
Westchester Summer Pool Pet Friendly Events Games

Ossining Vacation Rental Near River, Trails & Mta!

Ossining Vacation Rental Near River, Trails & Mta!
3.0 star property
Ossining
The price is CA $395
CA $1,184 total
includes taxes & fees
May 20 - May 21
Ossining Vacation Rental Near River, Trails & Mta!

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)
"Great place to stay."
United States
Sai
The price is CA $180
CA $207 total
includes taxes & fees
May 17 - May 18
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Hampton Inn Paramus

Hampton Inn Paramus
2.5 star property
Paramus
9.2 out of 10, Wonderful, (1,001 reviews)
"Excellent stay, rooms were clean, staff was helpful and friendly & breakfast was great."
United States
Carlos
The price is CA $168
CA $193 total
includes taxes & fees
May 25 - May 26
Hampton Inn Paramus

Marriott Park Ridge

Marriott Park Ridge
3.5 star property
Park Ridge
8.8 out of 10, Excellent, (941 reviews)
"Great stay"
United States
Caitlin
The price is CA $209
CA $240 total
includes taxes & fees
May 17 - May 18
Marriott Park Ridge

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (836 reviews)
"We had a clean and comfortable room at Heidi's. We will definitely stay there again!"
United States
Donna
The price is CA $203
CA $220 total
includes taxes & fees
May 17 - May 18
Heidi's Inn

HYATT house White Plains

HYATT house White Plains
3.0 star property
West Harrison
8.8 out of 10, Excellent, (1,042 reviews)
"The staff was so nice and the room was amazingly clean"
United States
Michelle
The price is CA $244
CA $279 total
includes taxes & fees
May 24 - May 25
HYATT house White Plains

Best Western The Inn at Ramsey-Mahwah

Best Western The Inn at Ramsey-Mahwah
3.0 star property
Ramsey
7.2 out of 10, Good, (1,003 reviews)
"Very nice staff "
United States
John
The price is CA $134
CA $154 total
includes taxes & fees
May 24 - May 25
Best Western The Inn at Ramsey-Mahwah

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
2.0 star property
Ardsley
8.8 out of 10, Excellent, (1,030 reviews)
"Breakfast was okay, room was clean and well maintained."
United States
Prema
The price is CA $152
CA $174 total
includes taxes & fees
May 17 - May 18
Ardsley Acres Hotel Westchester

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,107 reviews)
"Clean room, friendly staff, good breakfast!"
United States
Sarah
The price is CA $168
CA $206 total
includes taxes & fees
May 28 - May 29
Hampton Inn Harriman Woodbury

Comfort Inn Brewster

Comfort Inn Brewster
2.5 star property
Brewster
8.8 out of 10, Excellent, (566 reviews)
"It was home away from home, very quiet and relaxing. Staff was phenomenal "
United States
Lorether
The price is CA $209
CA $226 total
includes taxes & fees
May 27 - May 28
Comfort Inn Brewster

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built
3.0 star property
Bronx
8.2 out of 10, Very good, (547 reviews)
"The air conditioning was great, the bed was extremely comfortable it was like laying on a cloud, and the bathroom was beautiful."
United States
Gisela
The price is CA $197
CA $231 total
includes taxes & fees
May 20 - May 21
LIV Hotel Bronx - Newly Built

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
Tarrytown
8.2 out of 10, Very good, (1,080 reviews)
"Great place to stay"
United States
Deanna
The price is CA $186
CA $247 total
includes taxes & fees
May 17 - May 18
Tarrytown House Estate

Hilton Garden Inn Danbury

Hilton Garden Inn Danbury
3.0 star property
Danbury
8.4 out of 10, Very good, (1,000 reviews)
"I love very clean, Nice to go with the family 😍"
United States
Mayron
The price is CA $202
CA $232 total
includes taxes & fees
May 27 - May 28
Hilton Garden Inn Danbury

Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury
4.0 star property
Danbury
9.2 out of 10, Wonderful, (1,001 reviews)
"Super nice hotel, we thoroughly enjoyed our stay here. Highly recommend staying here."
United States
Joseph
The price is CA $230
CA $264 total
includes taxes & fees
May 17 - May 18
Hotel Zero Degrees Danbury

Clinton Inn Hotel & Event Center

Clinton Inn Hotel & Event Center
3.0 star property
Tenafly
7.6 out of 10, Good, (1,000 reviews)
"Our stay was great, the only down fall restaurant was closed. "
United States
Arlinda
The price is CA $166
CA $191 total
includes taxes & fees
May 21 - May 22
Clinton Inn Hotel & Event Center

Days Inn by Wyndham Nanuet / Spring Valley

Days Inn by Wyndham Nanuet / Spring Valley
2.0 star property
Nanuet
7.0 out of 10, Good, (1,003 reviews)
"Clean room and pleasant staff "
United States
Jay
The price is CA $127
CA $148 total
includes taxes & fees
May 18 - May 19
Days Inn by Wyndham Nanuet / Spring Valley

Holiday Inn Express Ramsey-Mahwah by IHG

Holiday Inn Express Ramsey-Mahwah by IHG
2.5 star property
Ramsey
9.2 out of 10, Wonderful, (1,001 reviews)
"Very good place to stay. Excellent breakfast, great beds/pillows, location, staff. Two thumbs up!"
United States
Robert
The price is CA $149
CA $170 total
includes taxes & fees
May 25 - May 26
Holiday Inn Express Ramsey-Mahwah by IHG

Best Western Paramus Hotel & Suites

Best Western Paramus Hotel & Suites
2.5 star property
Paramus
8.6 out of 10, Excellent, (1,019 reviews)
"Great place to stay room are clean, and the staff was great."
United States
Ramon
The price is CA $153
CA $175 total
includes taxes & fees
May 27 - May 28
Best Western Paramus Hotel & Suites
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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.

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 Waterfront: Enjoy beautiful views and relaxing strolls along the picturesque Ossining waterfront.
  • Outdoor Adventures: Explore nature preserves and hiking trails that offer a range of outdoor activities for all ages.
  • Cultural Experiences: Attend local theatre performances and engage with the vibrant arts scene in the community.
  • Family-Friendly Activities: Discover parks and recreational areas perfect for family outings and fun.
  • Diverse Accommodations: Choose from a variety of welcoming hotels and charming bed and breakfasts to suit your needs.

Find great hotels near Ossining

Discover a variety of welcoming accommodations in Ossining, New York, perfect for every type of traveller. Whether you're seeking a pet-friendly hotel, a charming bed and breakfast, or a convenient spot for business travel, you'll find options that cater to your needs. Explore affordable hotels and LGBTQIA-friendly stays, ensuring a comfortable and enjoyable experience during your visit to this delightful town.

  • Ramada by Wyndham Rochelle Park Near Paramus: This budget-friendly hotel is perfect for travellers seeking value without compromising comfort. Located 33.8km from Ossining, the Ramada offers a variety of dining options, including a daily buffet breakfast and an onsite restaurant. For those who enjoy staying active, the hotel features fitness facilities. Guests can unwind with premium TV channels and cable television in their rooms. The hotel is conveniently situated near a shopping district and a metro station, making it easy to explore the local attractions.
  • Homewood Suites by Hilton Teaneck Glenpointe: A 3-star gem, this hotel boasts an impressive guest rating of 9.2 out of 10, making it a top choice for business and leisure travellers alike. Located 33.8km from Ossining, it features spacious, pet-friendly suites, ideal for families or those travelling with furry companions. The hotel provides essential amenities for business travel, as well as a warm, inviting atmosphere. Guests appreciate the flexibility of being able to bring their pets, with fees waived for service animals, ensuring an inclusive and comfortable stay.
  • Baymont by Wyndham White Plains - Elmsford: With a guest rating of 8.2 out of 10, this budget-friendly hotel is well-suited for families and business travellers. Located just 11.3km from Ossining, it offers a range of child-friendly amenities, including free cribs and a first aid kit for peace of mind. The welcoming environment and convenient location make it an excellent choice for those looking to explore the area while enjoying a comfortable stay.

Where to stay in and around Ossining

Ossining, New York, offers a delightful blend of outdoor activities and family-friendly experiences. Nestled close to downtown and the eastern shore, this charming city invites you to explore its inviting atmosphere filled with friendly people. Nearby cities enhance your adventure with romantic settings and relaxing vibes, making it an ideal getaway for anyone seeking both excitement and tranquility. Your vacation in Ossining promises to create lasting memories for you and your loved ones.

  • Crotonville: Nestled in the heart of Ossining, Crotonville offers a delightful blend of outdoor adventure and scenic beauty. This charming village is perfect for those looking to explore nature reserves, mountains, and national parks nearby. With peak traveller arrivals in April to May and December, visitors can enjoy recreational areas and shopping centres year-round. The picturesque landscape provides an ideal backdrop for hiking and outdoor activities, making it a popular destination for adventure enthusiasts and nature lovers alike.
  • Maryknoll: Located a mere 3.2km from Ossining, Maryknoll is a vibrant city known for its family-friendly atmosphere and rich cultural experiences. With visitor numbers peaking in July to August and December, this city is home to significant architecture, historic buildings, and an art museum that showcases local talent. Sports enthusiasts can engage in baseball and soccer activities, making it a great spot for families looking to blend recreation with culture. Maryknoll's welcoming community and diverse offerings make it a must-visit destination.
  • Briarcliff Manor: Just 3.2km from Ossining, Briarcliff Manor is a picturesque city that offers a mix of family-oriented activities and urban charm. Visitors typically flock here in January and April to May, drawn by its shopping areas and modern squares. The city's vibrant atmosphere is ideal for those looking to experience a blend of city life and outdoor leisure. With various shopping centres and a welcoming community, Briarcliff Manor provides an enjoyable getaway that caters to families and city explorers alike.

Things to do near Ossining

Ossining offers a delightful mix of outdoor and urban activities perfect for families. Visitors can enjoy local theatre performances, explore shopping centres and various boutiques, and take advantage of recreational opportunities. For those seeking evening entertainment, the town also features night trips and campgrounds, making it an ideal destination for a memorable getaway.

Shopping

Ossining offers charming local shops for unique gifts and souvenirs. Visit the Ossining Farmers Market for local produce and crafts. If you're up for a drive, check out the nearby White Plains Galleria for a larger selection of stores and dining options.

Recreation

At The Golf Club at Mansion Ridge, indulge in a serene atmosphere with stunning golf courses and upscale dining. The Metropolitan Club and University Club, both exuding luxury, offer exclusive amenities and relaxation for members, making them perfect for unwinding after a day of exploration in Ossining.

Adventure

In Ossining, explore the scenic trails of the Old Croton Aqueduct State Historic Park, perfect for hiking or biking. Experience kayaking on the Hudson River for breathtaking views, or visit the nearby Croton Point Park for picnicking and nature walks amidst beautiful landscapes.

Nightlife

In Ossining, the lively atmosphere comes alive at venues like The Black Cow, known for its vibrant bar scene and live music. For a more relaxed evening, check out the local breweries offering craft beers and cozy vibes, perfect for unwinding after a day of exploring.

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

Booking tips and Expedia advantages for Ossining

  • 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: The cheapest time to book a hotel in Ossining is usually 1 month out from when you are planning to stay. If you're a little more spontaneous, you could also peruse Expedia's last minute deals which could secure you a cheaper stay. Look out for the green banner below the price to spot the deals.
  • 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: Utilize Expedia’s search tool to refine your choices based on your budget, desired location, and preferred hotel type. To discover the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Ossining with your flights and activities through an Expedia package.

Find the best attractions in Ossining

Ossining, New York, offers an excellent mix of outdoor and family-friendly activities, making it ideal for a city-themed vacation. Explore local highlights such as nature preserves, urban parks, and arts centres while enjoying the rich cultural experiences available. Nearby attractions, including the Hudson Hills and Westin hotels, enhance your stay, ensuring a memorable visit filled with adventure and relaxation.

  • Sing Sing Correctional Facility: This historic prison, located in Ossining, offers a unique glimpse into the American penal system. Its imposing structure and rich history provide an intriguing backdrop, showcasing the cultural significance of correctional facilities in society.
  • Sing Sing Prison Museum: Adjacent to the correctional facility, this museum delves into the history of Sing Sing, featuring exhibits that highlight the lives of inmates and the evolution of the justice system. The cultural vibes here make it a thought-provoking experience.
  • Nelson Park: A vibrant urban park perfect for families, Nelson Park features lush greenery, playgrounds, and scenic walking paths. It’s an ideal spot to relax, enjoy the outdoors, and immerse yourself in the local community atmosphere.

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

For your visit to Ossining, New York, you can choose from three major airports. John F. Kennedy International Airport (JFK) is 57.9km away, with nearby hotels like the 5-star Arlo Williamsburg and The William Vale, both 17.7km from the airport. Newark Liberty International Airport (EWR) is 59.5km away, featuring luxurious options such as The Dominick and Four Seasons Hotel New York Downtown, both 14.5km from EWR. Lastly, LaGuardia Airport (LGA) is 43.5km distant, with excellent accommodations like The Plaza and The Pierre, each 8.0km away. These hotels offer convenient transportation services to their respective airports for a hassle-free experience.

Frequently asked questions

What is the best area to stay in Ossining?
The best areas to stay in Ossining are the downtown waterfront district and the quieter residential areas further up the hill.

The downtown waterfront area offers direct access to the Hudson River and its scenic views. This area is home to the Ossining train station, making it incredibly convenient for those travelling into New York City. You'll find a growing number of local eateries and shops along Main Street and near the waterfront, along with parks like Louis Engel Waterfront Park. This area is well-suited for visitors who want to be close to transportation and enjoy river activities.

Couples often appreciate the downtown area for its easy access to waterfront dining options and the convenience of the train for day trips. The ability to stroll along the riverfront at sunset or enjoy a meal with a view provides a relaxed and enjoyable experience.

For those seeking a more tranquil setting, the residential areas further up the hill from the waterfront offer a peaceful escape. These neighbourhoods are characterised by tree-lined streets and larger properties, providing a quiet and pleasant environment. While still within easy reach of downtown by car or a short walk, they offer a sense of calm away from the busier areas.

Families might find these quieter residential parts of Ossining appealing. The wider streets and less crowded feel can be more comfortable, and many properties in these areas offer more space.
What are the best family hotels in Ossining?
For family-friendly accommodation in Ossining, the Windrose On Hudson is a highly-rated option.

This 3-star hotel, with an 8.0 rating, offers several convenient amenities for families, including complimentary cribs and free self-parking. Guests will also appreciate the free WiFi and accessible fitness facilities. The Windrose On Hudson is well-located for exploring local attractions such as Van Cortlandt Manor, just 1.2 km away, and Crawbuckie Park, which is 2.2 km from the hotel.
What are the best budget hotels in Ossining?
For an excellent budget hotel in Ossining, the Windrose On Hudson is a fantastic option.

This 3-star hotel, with an 8.0 rating, offers complimentary self-parking and free WiFi, which are always appreciated by travellers. Guests can also make use of the fitness facilities, which are accessible. Its convenient location places it near several local attractions, including Van Cortlandt Manor, just 1.2 km away, and Ossining Dog Park, a mere 0.8 km distance. View all budget hotels in Ossining
What are the best hotels in Ossining near Croton Point Park?
For a hotel in Ossining near Croton Point Park, consider the Windrose On Hudson.

The 3-star Windrose On Hudson, with an 8.0 rating, is conveniently located just 2.7 kilometres from Croton Point Park. This hotel offers free self-parking and free WiFi, making it easy for families travelling by car. Guests can also benefit from accessible fitness facilities and free cribs, suiting those with young children.
When is the best time to go to Ossining?
The best time to go to Ossining is during the late spring (May to early June) or early autumn (September to October) when the weather is most pleasant for outdoor activities and exploring the area.

During late spring, the temperatures are mild, and the local flora is in full bloom, making it ideal for enjoying the numerous parks and waterfront areas along the Hudson River. You'll find comfortable conditions for walks, picnics, and boat trips without the peak summer crowds or heat.

Early autumn brings cooler, crisp air and the spectacular colours of the changing leaves, especially along the Hudson Valley. This period is superb for scenic drives, hiking, and visiting local farms and markets.
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?
Members always get our best prices. Find our best Ossining hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
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 CA $133 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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