Pleasantville holiday homes, NY, USA: holiday houses & more

Discover a selection of holiday rentals in Pleasantville that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as parking and a pool. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find the best place to stay - Pleasantville

Cozy house on the Hudson

Sleeps 2 · 1 bedroom · 1 bathroom

Luxurious & Historic Orchard Hill Estate farmhouse/mansion built 1859

Unforgettable Lux Country Mansion Villa, Pool, Pets, 1 hr NYC, Hot Tub, Fire Pit

Sleeps 25 · 8 bedrooms · 5 bathrooms

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

Find the perfect holiday rental for your Pleasantville getaway

The wildlife and other outdoor surroundings create an inviting atmosphere in Pleasantville. Renowned for its hiking, restaurants and cycling, this city welcomes all visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Pleasantville

Are you looking for attractions to see while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Pleasantville a fun place to get away to. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Rockland Lake State Park Championship Golf Course (6.7 mi / 10.7 km)
Rockland Bakery (11 mi / 17.7 km)
Blue Hill Golf Course (11.6 mi / 18.7 km)
Legoland Discovery Center Westchester (12.1 mi / 19.4 km)
Rye Playland (13.1 mi / 21.1 km)
Dunwoodie Golf Course (14.3 mi / 23 km)

Exploring the natural features in Pleasantville

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Pleasantville. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

Rockefeller State Park Preserve (2.8 mi / 4.5 km)
Rockwood Hall Park (3.9 mi / 6.3 km)
Croton Point Park (6.3 mi / 10.1 km)
Nyack Beach State Park (6.3 mi / 10.1 km)
Rockland Lake State Park (6.9 mi / 11.1 km)
Buttermilk Falls Park (8.7 mi / 14 km)

Transport to and around Pleasantville

The nearest airport is in White Plains, NY (HPN-Westchester County), located 6.4 mi (10.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 22.9 mi (36.9 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Pleasantville?

Property type, length of stay and season are some of the things that can affect the price of a holiday home. Simply click on your dates of travel to find your perfect fit. From cosy cabins to sprawling luxury villas, all Bookabach holiday homes provide incredible value.

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

The average price for a holiday home near the beach in Pleasantville will depend on when you'll be there and the size and style of property you're searching for. Find prices easily on Bookabach by entering your destination and preferred travel dates. Then use the filters to choose the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.

What are the top attractions for families in Pleasantville?

Keeping the kids happy during your stay in Pleasantville is easy with these cool family-friendly attractions:

Jacob Burns Film Centre Media Arts Lab
Hardscrabble Wilderness Area
Rockefeller State Park Preserve

How old do you have to be to rent a holiday home in Pleasantville?

We recommend you check with the Pleasantville holiday home you're considering on Bookabach as the age limit varies. However, generally it's 16, 18 or 21.

How long can I rent a holiday home in Pleasantville for?

The amount of time you can book a Pleasantville holiday home for is down to the property. Just enter your dates of travel to see available options offering longer term stays. They have all you need to make your extended break more enjoyable and convenient, like air conditioning and kitchens. Some properties may also offer discounted weekly or monthly prices, so you can stick around for longer for less.