Ossining Vacation Rentals, New York: homes, house rentals & more

Discover a selection of 8 homes and other vacation rentals in Ossining that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you expect for your stay, which might include parking and a washer and dryer. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

Find properties near top attractions in Ossining

Teatown Lake Reservation

Find the best place to stay - Ossining

Cozy house on the Hudson

Sleeps 2 · 1 bedroom · 1 bathroom

Top rated rentals - Ossining

Fabulous getaway

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The natural setting of Ossining is ready to explore

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. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Ossining

Do you want to discover things to do during your stay? Venture out of your vacation home and check out everything that makes Ossining a one-of-a-kind vacation spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

Rockland Bakery (8.4 mi / 13.5 km)
Blue Hill Golf Course (10.1 mi / 16.3 km)
Stanwich Club (12.5 mi / 20.2 km)
Legoland Discovery Center Westchester (13.6 mi / 21.9 km)
Dunwoodie Golf Course (15.7 mi / 25.2 km)
Emerson Golf Club (15.7 mi / 25.3 km)

Exploring the natural features in Ossining

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Ossining is a great place to get outside. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

Croton Point Park (2.2 mi / 3.5 km)
Rockwood Hall Park (3.5 mi / 5.7 km)
Nyack Beach State Park (4 mi / 6.4 km)
Rockefeller State Park Preserve (4 mi / 6.4 km)
Rockland Lake State Park (4 mi / 6.4 km)
Buttermilk Falls Park (6.9 mi / 11.1 km)

How to get to and around Ossining

The nearest airport is in Westchester County Airport (HPN), located 10.5 mi (16.8 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Teterboro, NJ (TEB), which is 23.9 mi (38.5 km) away.

If you're traveling by train, the main station is Ossining Station.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Ossining?

The most sought-after types of vacation rentals in Ossining are houses. After something a little different? Vrbo has plenty of options to match our guests' diverse needs, so you'll see vacation homes in all shapes and sizes, and for all budgets. The perfect fit is ready and waiting for you — find yours today.

How much does it cost to rent a vacation rental in Ossining?

Season, property type and length of stay are some of the conditions that can determine the price of a vacation home. Simply add your dates of travel to find the ultimate escape. From cozy cabins to expansive luxury villas, all Vrbo vacation rentals offer incredible value.

How much does it cost to rent a beach house in Ossining?

The average price for a vacation rental near the beach in Ossining depends on when you're going and the style and size of property you want. Find prices easily on Vrbo by entering your destination and preferred travel dates. Then use our filter tool to select the number of bedrooms and amenities that you prefer, like WiFi, air conditioning and a hot tub.

Are there pet-friendly vacation rentals in Ossining?

Yes, there are. You'll find three stays that allow pets in Ossining on Vrbo. Our furry kids need a break too, so simply use our search function for pet-friendly vacation rentals to find a perfect pad where your pup can get in on the family fun.

What are popular rental amenities in Ossining?

When it comes to rental amenities that guests look for in Ossining, a firepit, a nearby river and a swimming pool rank the highest. With Vrbo vacation homes, you'll enjoy options to fit your taste and style, whether you're traveling with family, friends or even pets.

Are there vacation rentals in Ossining that welcome kids?

With three family-friendly vacation homes to pick from in Ossining, now is an awesome time to introduce your kids to the wonders of travel. Just check our "Properties good for families" filter to look for stays that come with amenities perfect for vacationing families, such as full kitchens, yards, hot tubs and entertainment areas.

What are the top attractions for families in Ossining?

There are loads of fabulous things to see and do with the family in Ossining, such as:

Rockefeller Archive Center
Palisades Climb Adventure
Peekskill Museum

How can I find vacation rentals with air conditioning in Ossining?

Ossining has three vacation rentals where you can relax and recharge in air-conditioned comfort. To locate a property on Vrbo that features this perk, choose your travel dates and use the filters to select the "air conditioning" box.

How old do you have to be to rent a vacation rental in Ossining?

The minimum age is generally 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your preferred Ossining vacation rental before booking your stay.

How long can I rent a vacation rental in Ossining for?

It really depends on the Ossining property. To view all available options offering extended stays, simply type your travel dates and number of people into the Vrbo search page. You can enjoy having the whole place to yourself, as well as comforts such as air conditioning, a fully-equipped kitchen and a yard to play in. Keep an eye out for long-term stays that offer weekly or monthly discounts.