Destination guide

Delight in the natural landscape of Ossining

The area's monuments and museums are just a few of the reasons to vacation in Ossining. This city's restaurants, parks and golfing draw many visitors. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.


Activities and attractions in Ossining

Are you searching for top things to see and do while you're in the area? Venture out of your cozy vacation rental and check out everything that makes Ossining a one-of-a-kind vacation spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Hudson Hills Golf Course (0.8 mi / 1.3 km)
  • Rockland Lake State Park Championship Golf Course (5.3 mi / 8.5 km)
  • Mohansic Golf Course (5.6 mi / 9.1 km)
  • Rockland Lake State Park Executive Golf Course (6.4 mi / 10.3 km)
  • Hudson Highlands Cruises (7.3 mi / 11.7 km)
  • Muscoot Farm (7.3 mi / 11.8 km)
Natural features

Exploring the natural landscape of Ossining

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Ossining is a great place to get outside. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Teatown Lake Reservation (1.4 mi / 2.2 km)
  • Snowden Avenue Park (2.7 mi / 4.4 km)
  • Kitchawan Preserve (3 mi / 4.9 km)
  • Nelson Park (3.1 mi / 5 km)
  • Louis Engel Waterfront Park (3.1 mi / 5.1 km)
  • Croton Landing Park (3.4 mi / 5.5 km)
How to get there

Traveling to and around Ossining

The nearest airport is in White Plains, NY (HPN-Westchester County), located 10.8 mi (17.4 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 21.9 mi (35.2 km) away.

If you prefer train travel, the main station serving the city is Ossining Station.

Where to stay around Ossining?

Our 2019 property listings offer a large selection of 66 vacation rentals near Ossining. From 48 Houses to 4 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Ossining for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Ossining?

HomeAway offers a large selection of vacation rentals near lovely places in Ossining. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Snowden Avenue Park: 237 vacation rentals
  • Sing Sing Prison Museum: 237 vacation rentals
  • Kitchawan Preserve: 230 vacation rentals
  • Teatown Lake Reservation: 231 vacation rentals
  • Ossining Historical Society: 237 vacation rentals

But there are many other points of interest around Ossining listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Ossining?

Yes, of course. HomeAway has 48 Houses in Ossining. Our other popular types of vacation rentals in Ossining include:

  • Condos/Apartments: 4 rentals available
  • Cabins: 3 rentals available
  • Cottages: 3 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Ossining?

Yes, you can select your preferred vacation rental with pool among our 25 vacation rentals with pool available in Ossining. Please use our search bar to access the selection of vacation rentals available.

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