Pleasantville vacation rentals

We found 163 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Pleasantville that are perfect for your trip. Vacation homes offer the amenities you expect for your family, friends, or furry companion, like air conditioning and WiFi. At the end of the day, you're sure to find a rental that has what everyone needs, including accessible or non-smoking choices.
  • 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, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Find the perfect vacation rental for your Pleasantville getaway

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

Sightseeing in and around Pleasantville

Do you want to discover top things to see and do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Pleasantville has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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)
  • New York Country Club (13.6 mi / 21.8 km)

Exploring the natural features in Pleasantville

Whether you're an active traveler or just want to take in the scenery, Pleasantville is a great place to spend some time outside. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Rockefeller State Park Preserve (2.8 mi / 4.5 km)
  • Pierson Park (5.5 mi / 8.9 km)
  • Teatown Lake Reservation (5.7 mi / 9.1 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)

Transportation to and around Pleasantville

The nearest airport is in Westchester County Airport (HPN), located 6.4 mi (10.3 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into 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 vacation rental in Pleasantville?
Property type, length of stay and season are some of the things that can affect the price of a vacation home. Simply click on your dates of travel to find your perfect fit. From cozy cabins to sprawling luxury villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Pleasantville?
The average price for a vacation rental 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 Vrbo 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 Center Media Arts Lab
  • Hardscrabble Wilderness Area
  • Rockefeller State Park Preserve

How old do you have to be to rent a vacation rental in Pleasantville?
We recommend you check with the Pleasantville vacation home you’re considering on Vrbo as the age limit varies. However, generally it’s 16, 18 or 21.
How long can I rent a vacation rental in Pleasantville for?
The amount of time you can book a Pleasantville vacation rental 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.

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