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Our top choices for Ossining hotels

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.6 out of 10, Excellent, (177 reviews)
"Ev chargers on site. Lovely grounds and facilities. Will definitely stay here next time i am in the area."
United States
Andrew
The price is CA $280
CA $312 total
includes taxes & fees
Jul 2 - Jul 3
Windrose On Hudson

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is CA $1,418
CA $2,265 total
includes taxes & fees
Jul 1 - Jul 2
Summer Pool Oasis Custom Bar Arcade Pool Table

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very good, (64 reviews)
"Family trip with 3 kids and we love it"
Canada
Pheng Theam
The price is CA $156
CA $192 total
includes taxes & fees
Jul 21 - Jul 22
Comfort Suites Central Valley - Woodbury

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, (389 reviews)
"Great place to stay."
United States
Sai
The price is CA $173
CA $199 total
includes taxes & fees
Jul 5 - Jul 6
Holiday Inn Express Hotel & Suites Danbury - I-84 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, (1,009 reviews)
"It was a beautiful stay."
United States
Shayla
The price is CA $210
CA $258 total
includes taxes & fees
Jul 8 - Jul 9
Overlook Lodge at Bear Mountain

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (862 reviews)
"I had a lovely stay - highly recommend!"
United States
Catherine
The price is CA $210
CA $227 total
includes taxes & fees
Jul 1 - Jul 2
Heidi's Inn

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
8.0 out of 10, Very good, (1,273 reviews)
"Hotel and visit were great, definitely recommend."
United States
Kathryn
The price is CA $141
CA $162 total
includes taxes & fees
Jul 5 - Jul 6
Ethan Allen 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, (747 reviews)
"Great stay, beautiful hotel and staff was great"
United States
Amanda
The price is CA $233
CA $313 total
includes taxes & fees
Jul 1 - Jul 2
The Thayer Hotel at West Point

West Gate Inn Nyack

West Gate Inn Nyack
3.0 star property
Nyack
7.2 out of 10, Good, (1,352 reviews)
"Great location. Amazing breakfast."
United States
Gareth
The price is CA $134
CA $153 total
includes taxes & fees
Jul 2 - Jul 3
West Gate Inn Nyack

Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1,003 reviews)
"Safe area not too far from restaurants and stores."
United States
Richard
The price is CA $121
CA $149 total
includes taxes & fees
Jul 2 - Jul 3
Americas Best Value Inn at Central Valley-Woodbury

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built
3.0 star property
Bronx
7.2 out of 10, Good, (842 reviews)
"Very accommodating staff and great location in a time of emergency stay"
United States
Guap
The price is CA $179
CA $210 total
includes taxes & fees
Jul 7 - Jul 8
LIV Hotel Bronx - Newly Built

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, (1,006 reviews)
"Had a pleasant stay very clean and alot of options for the breakfast."
United States
IMRAN
The price is CA $145
CA $166 total
includes taxes & fees
Jul 6 - Jul 7
Best Western The Inn at Ramsey-Mahwah

Comfort Inn Brewster

Comfort Inn Brewster
2.5 star property
Brewster
8.8 out of 10, Excellent, (576 reviews)
"Nice hotel clean comfortable & easy off highway ."
United States
CIRA
The price is CA $204
CA $221 total
includes taxes & fees
Jul 26 - Jul 27
Comfort Inn Brewster

Hilton Garden Inn Danbury

Hilton Garden Inn Danbury
3.0 star property
Danbury
8.4 out of 10, Very good, (1,003 reviews)
"Great atmosphere and the food and drinks were great. Quiet and restful."
United States
Rose
The price is CA $185
CA $213 total
includes taxes & fees
Jul 12 - Jul 13
Hilton Garden Inn Danbury

Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury
4.0 star property
Danbury
9.2 out of 10, Wonderful, (1,002 reviews)
"Great place to step in the area the restaurant in the lobby is awesome great food and ambiance"
United States
Laura
The price is CA $240
CA $276 total
includes taxes & fees
Jul 6 - Jul 7
Hotel Zero Degrees Danbury

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,120 reviews)
"I enjoyed my stay. The place was absolutely clean. Free breakfast was amazing and I will be going again"
United States
Khaleem
The price is CA $197
CA $242 total
includes taxes & fees
Jul 7 - Jul 8
Hampton Inn Harriman Woodbury

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, (1,007 reviews)
"It was our second visit to this hotel and the hotel is neat, clean and centrally located for visiting the area."
United States
Susan
The price is CA $179
CA $205 total
includes taxes & fees
Jul 30 - Jul 31
Holiday Inn Express Ramsey-Mahwah by IHG

West Point Motel

West Point Motel
2.5 star property
Highland Falls
8.6 out of 10, Excellent, (717 reviews)
"Stayed here numerous times friendly staff and very nice place close to post."
United States
Michael
The price is CA $170
CA $210 total
includes taxes & fees
Jul 19 - Jul 20
West Point Motel

Red Carpet Inn

Red Carpet Inn
2.0 star property
Cove - East Side - Shippan
6.8 out of 10, (1,014 reviews)
"I enjoyed my stay amazing food places around and comfortable"
United States
Alonzo
The price is CA $104
CA $120 total
includes taxes & fees
Jul 5 - Jul 6
Red Carpet Inn

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
2.0 star property
Ardsley
8.8 out of 10, Excellent, (1,067 reviews)
"Awesome place"
United States
Mark
The price is CA $172
CA $197 total
includes taxes & fees
Jul 13 - Jul 14
Ardsley Acres Hotel Westchester
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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.

A historic stone building with a large circular window and a tower with a green roof.
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 $120 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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