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.

How many vacation rentals are available around Ossining?

Our 2020 vacation rental listings offer a large selection of 66 house rentals around Ossining. From 51 Houses to 3 Condos/Apartments, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Ossining is on HomeAway.

What is the best area to stay when travelling to Ossining?

Whether you're travelling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Ossining:

  • Manhattan: 2,972 vacation rentals
  • Bronx: 1,863 vacation rentals
  • Fort George: 19 vacation rentals
  • West Bronx: 183 vacation rentals
  • Williamsbridge: 22 vacation rentals

For other neighbourhoods, please use our search bar to access the selection of vacation rentals available.

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

HomeAway offers a large selection of lodging choices 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:

  • Ossining Historical Society: 240 home rentals
  • Sing Sing Prison Museum: 236 home rentals
  • Merchants Square: 232 home rentals
  • Teatown Lake Reservation: 231 home rentals
  • Sing Sing Correctional Facility: 245 home 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 51 Houses in Ossining. Our other popular types of vacation rentals in Ossining include:

  • Condos/Apartments: 3 lodging choices
  • Cabins: 3 lodging choices
  • Cottages: 3 lodging choices

But you can also enjoy a great stay in one of our other vacation homes 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 20 vacation homes with pool available in Ossining.

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