Discover a selection of 63 vacation rentals in Ossining, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $105 per night, and studios and condos are popular options for a stay in Ossining. Either way, you'll find a rental for everyone's needs.
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, NY?

Our 2020 property listings offer a large selection of 63 vacation rentals around Ossining. From 3 studio vacation rentals to 2 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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

Whether you're traveling 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: 3,124 vacation rentals
  • Bronx: 2,054 vacation rentals
  • West Bronx: 192 vacation rentals
  • Fort George: 23 vacation rentals
  • Williamsbridge: 22 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to Ossining?

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

  • Sing Sing Prison Museum: 253 vacation rentals
  • Sing Sing Correctional Facility: 262 vacation rentals
  • Snowden Avenue Park: 254 vacation rentals
  • Teatown Lake Reservation: 244 vacation rentals
  • Kitchawan Preserve: 248 vacation rentals

But there are many other points of interest around Ossining listed on Vrbo 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 Studios in Ossining?

Yes, of course. Vrbo has 3 Studios in Ossining. Our other popular types of vacation rentals in Ossining include:

  • Condos/Apartments: 2 rentals available
  • Houses: 48 rentals available
  • Cabins: 3 rentals available

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

Can I find a vacation rental with pool in Ossining?

Yes, you can select your preferred vacation rental with pool among our 18 vacation rentals with pool available in Ossining. Please use our search bar to access the selection of vacation rentals available.

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