Choose from 9 vacation rentals located in Ossining, New York. Top filters in Ossining include Kitchen / Kitchenette, Air conditioner, and Internet / Wifi. Prices range from $93 to $1,144 per night. Our most popular vacation rental types near Ossining are Condo and Hotel.

Top vacation rentals in Ossining

Property grounds
5.0
Outstanding(5 Reviews)
House
 in Ossining
Neighbor's house - Welcome!
6 guests · 2 bedrooms · 2 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Ossining, at $169 per night for your next great vacation.

$$$$
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Property grounds
4.8
Outstanding(33 Reviews)
House
 in Ossining
Cozy house on the Hudson
2 guests · 1 bedroom · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Experience the best of Ossining with this House available for $225. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Entrance.
5.0
Outstanding(11 Reviews)
Bed and Breakfast
 in Briarcliff Manor
Beautiful Brand New Private Duplex Unit in Lower Hudson Valley "Stone Haven"
5 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen / Kitchenette

Looking to create some memories in Ossining? Look no further than our Bed and Breakfast, Beautiful Brand New Private Duplex Unit in Lower Hudson Valley "Stone Haven". Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property view
Condo
 in Cornwall (US)
Tudoresque
10 guests · 5 bedrooms · 5 baths
Pool · Pets allowed · Family friendly

Looking for a Condo in Ossining, this Condo for $1,144 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Ossining

Ossining travel guide

Let us help you plan your perfect Ossining vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Ossining, and more.

Frequently asked questions

What do I need to know before visiting Ossining, NY?

Before visiting Ossining, NY, it is important to know that the town is located in the Hudson Valley, close to the New York City metro area. It is a picturesque historic community with plenty of outdoor activities to explore. Here are a few more key points to consider:

  • The town has a rich history, with plenty of historical sites to visit
  • Outdoor activities include kayaking, biking, and hiking
  • The town is close to many cultural attractions like the Ossining Public Library and the Teatown Lake Reservation

What are the must-visit tourist attractions in Ossining, NY?

Ossining, NY has some of the most incredible tourist attractions. Here are the must-visit spots to check out:

  • Teatown Lake Reservation
  • Ossining Historical Society
  • Ossining Public Library
  • John D. Barrow Art Gallery

Teatown Lake Reservation is a great destination for outdoor enthusiasts, offering hiking, fishing, and more. Ossining Historical Society is a great spot to learn about the area's history. Ossining Public Library is a great spot to relax and read. Finally, the John D. Barrow Art Gallery is a great place to view some art from local and international artists.

How can I get around in Ossining, NY?

You can get around Ossining, NY in a variety of ways:

  • By car
  • By bus
  • By bike

The Bee-Line bus network offers multiple routes, and there are bike lanes and trails located throughout the town of Ossining. You can also take a taxi or ride-sharing service to get around.

Where can I find affordable accommodation in Ossining, NY?

Ossining, NY offers a variety of affordable accommodation options. Here are a few of the best:

  • The Hampton Inn & Suites Tarrytown/Greenburgh: Located near the Hudson River, this hotel offers comfortable rooms and a great location for exploring the area.
  • The Tarrytown House Estate: This historic estate offers a variety of rooms and suites, plus a range of amenities.
  • The DoubleTree Tarrytown: This hotel offers comfortable rooms and suites with all the amenities you need for a comfortable stay.
  • The Comfort Inn & Suites Tarrytown: This hotel offers cozy rooms and suites, plus a complimentary breakfast.

What is the culture like in Ossining, NY?

Ossining, NY is a vibrant community that offers a unique blend of diverse cultures, activities, and events. It is a place where people of all backgrounds can come together to create a vibrant and thriving community. Here are five key elements of Ossining's culture:

  • A strong sense of community pride and spirit
  • A welcoming and diverse population
  • An abundance of outdoor activities
  • An array of cultural and entertainment offerings
  • A rich history and cultural heritage
Ossining is a great place to live and work, and its culture is a big part of what makes it such an attractive and vibrant community.

Is Ossining, NY safe to travel to?

Ossining, NY is generally safe to travel to. Here are a few tips to help you stay safe:

  • Be aware of your surroundings and stick to well-lit and populated areas.
  • Avoid carrying large sums of cash or valuables with you.
  • Be aware of local laws and customs.

What are the popular shopping destinations in Ossining, NY?

Ossining, NY is home to a variety of popular shopping destinations. Here are a few of the most popular:

  • The Shops at Croton Landing
  • Galleria at Crystal Run
  • The Westchester Mall

What are the best neighborhoods to visit in Ossining, NY?

The best neighborhoods to visit in Ossining, NY are:

  • Downtown Ossining
  • Croton-on-Hudson
  • Briarcliff Manor

Downtown Ossining is a vibrant area with shops, restaurants, and entertainment. Croton-on-Hudson is a picturesque village on the banks of the Hudson River. Briarcliff Manor is a charming village with beautiful homes and a historic main street.

Where is Ossining, NY?

Ossining, NY is located in Westchester County, about 30 miles north of New York City. It is situated along the Hudson River and is known for its historic architecture, including the Ossining Union Free School District Administration Building, which is listed on the National Register of Historic Places. The town also contains the Ossining Public Library, which is the oldest library in continuous use in Westchester County.

What are the most popular vacation rental amenities in Ossining, NY?

Popular vacation rental amenities in Ossining, NY include:

  • Spacious living areas
  • Modern kitchens with appliances
  • Outdoor patios and decks
  • Hot tubs and swimming pools
  • Fitness centers

Additionally, many vacation rentals in Ossining, NY have access to nearby restaurants, shops, and entertainment venues. Some rentals even offer concierge services, which can help guests make the most of their stay.

What are the top things to do in Ossining, NY?

Ossining, NY has plenty of activities to explore and enjoy. From its beautiful nature spots to its historical museums, there's something for everyone. Here are some of the top things to do in Ossining:

  • Visit the Olana State Historic Site, a historic home and landscape designed by artist Frederic Church.
  • Go fishing, canoeing, and kayaking at Teatown Lake Reservation.
  • Explore the expansive Rockefeller State Park Preserve.
  • View the art exhibits at the Osining Arts Council Gallery.

What is the price range for rentals in Ossining?

Vacation rentals in Ossining have a price range between $93-$1,144. The average price for rentals in Ossining is $225 per night.

What are the most popular vacation rental amenities in Ossining?

  • Kitchen / Kitchenette
  • Air conditioner
  • Internet / Wifi

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