Photo by Linda Zanetti

Ossining holiday rentals

We found 139 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 6 homes and other holiday rentals in Ossining that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. You're sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The natural setting of Ossining is ready to explore

The area's monuments and museums are just some of the reasons to come on holiday to Ossining. This city's restaurants, parks and golfing draw many visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday 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 find top things to see and do while you're in the area? Venture out of your holiday home and check out everything that makes Ossining a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Rockland Bakery (8.4 mi / 13.5 km)
  • Legoland Discovery Center Westchester (13.6 mi / 21.9 km)
  • Dunwoodie Golf Course (15.7 mi / 25.2 km)
  • Rye Playland (16.8 mi / 27 km)
  • Rockland Lake State Park Championship Golf Course (3 mi / 4.9 km)
  • Hilltop Hanover Farm and Environmental Center (7.7 mi / 12.4 km)

Exploring the natural features in Ossining

Whether you're looking for adventure or just want to appreciate the scenery, Ossining is a great place to get out in nature. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Croton Point Park (2.2 mi / 3.5 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)
  • Franklin D. Roosevelt State Park (8.9 mi / 14.3 km)

How to get to and around Ossining

The nearest airport is in White Plains, NY (HPN-Westchester County), located 10.5 mi (16.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Teterboro, NJ (TEB), which is 23.9 mi (38.5 km) away.

If you'd rather travel by train, the main station is Ossining Station.

Frequently asked questions

What is the most popular type of holiday home accommodation in Ossining?

The most sought-after types of holiday homes in Ossining are houses. After something a little different? Stayz has plenty of options to match our guests' diverse needs, so you'll see holiday 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 holiday home in Ossining?

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

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

The average price for a holiday home near the beach in Ossining depends on when you're going and the style and size of property you want. Find prices easily on Stayz 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 holiday homes in Ossining?

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

What are popular home amenities in Ossining?

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

Are there holiday homes in Ossining that welcome kids?

With three family-friendly holiday 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 holidaying 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 Centre
  • Palisades Climb Adventure
  • Peekskill Museum

How can I find holiday homes with air conditioning in Ossining?

Ossining has three holiday homes where you can relax and recharge in air-conditioned comfort. To locate a property on Stayz 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 holiday home in Ossining?

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

How long can I rent a holiday home 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 Stayz 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.

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