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Pleasantville overview

Pleasantville is a small town unique for its wineries and ruins. You'll enjoy Pleasantville's riverfront and historical sites, along with outdoor areas for biking and hiking. Take a campus tour or explore the surrounding area of Sarah Lawrence College. Make some memories at Jacob Burns Film Center Media Arts Lab and Jacob Burns Film Center Theater. Pleasantville is a family- and business-friendly destination with something for everyone.

Where to stay in Pleasantville

Whether you're planning to stay for a night or for the week, the area around Pleasantville has accommodations to fit every need. Search for hotels in Pleasantville with Hotels.com by checking our online map. Our maps display the areas and neighborhoods around all Pleasantville hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Pleasantville hotel deals are here with our lowest price guarantee.

How to get to Pleasantville

Fly in to White Plains, NY (HPN-Westchester County), 6.1 mi (9.9 km) from downtown Pleasantville. New York, NY (LGA-LaGuardia) is the next closest major airport, 24.7 mi (39.8 km) away.

What to see around Pleasantville

Fun activities are on hand such as biking, ice skating, and wine tasting, along with attractions such as:
  • • Hardscrabble Wilderness Area
  • • Rockefeller State Park Preserve
  • • Nelson Park
  • • Nyack Beach State Park
  • • Memorial Park
Family-friendly attractions include:
  • • Sportime USA
  • • Westchester Skating Academy
  • • Hudson Highlands Cruises
  • • Legoland Discovery Center Westchester
  • • Untermyer Gardens Conservancy
Memorable for its historical sites, ruins, and these top landmarks to visit:
  • • Sleepy Hollow Cemetery
  • • Old Dutch Church of Sleepy Hollow
  • • Philipsburg Manor
  • • Tarrytown Lighthouse
  • • Indian Burial Mound
Its riverfront and hiking trails offer a glimpse of the natural beauty, and favorite spots for nature lovers include:
  • • Rockwood Hall Park
  • • Pleasant Square
  • • Merchants Square
  • • Louis Engel Waterfront Park
  • • Depot Square
Here are some top sights to see:
  • • Jacob Burns Film Center Media Arts Lab
  • • Jacob Burns Film Center Theater
  • • New York Medical College
  • • Union Church of Pocantico Hills
  • • Rockefeller Archive Center

When to visit Pleasantville

Curious about when's the best time to visit? Here are the seasonal norms to help with your planning:

Seasonal temperature averages
  • January-March: 52°F day, 21°F night
  • April-June: 80°F day, 35°F night
  • July-September: 82°F day, 49°F night
  • October-December: 67°F day, 23°F night
Seasonal rainfall averages
  • January-March: 11.42 inches
  • April-June: 12.80 inches
  • July-September: 12.60 inches
  • October-December: 12.72 inches