Discover a selection of 86 vacation rentals in Pleasantville, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $64 per night, and houses and condos are popular options for a stay in Pleasantville. Either way, you'll find a rental for everyone's needs.
Destination guide

Choose a vacation rental for your Pleasantville getaway

The wildlife and other outdoor surroundings create an inviting atmosphere in Pleasantville. This city's hiking, restaurants and biking draw many visitors. Many of our vacation rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.


Activities and attractions in and around Pleasantville

Do you want to discover attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Pleasantville has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Sportime USA (4.3 mi / 6.9 km)
  • Westchester Skating Academy (4.3 mi / 7 km)
  • Hudson Hills Golf Course (5.2 mi / 8.4 km)
  • Griffith E. Harris Golf Course (5.6 mi / 9 km)
  • Rockland Lake State Park Executive Golf Course (6.5 mi / 10.5 km)
  • Rockland Lake State Park Championship Golf Course (6.7 mi / 10.8 km)
Natural features

Exploring the natural features in Pleasantville

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

  • Hardscrabble Wilderness Area (1.5 mi / 2.4 km)
  • Rockefeller State Park Preserve (2.4 mi / 3.8 km)
  • Rockwood Hall Park (3.7 mi / 6 km)
  • Nelson Park (4 mi / 6.5 km)
  • Louis Engel Waterfront Park (4.5 mi / 7.2 km)
  • Snowden Avenue Park (4.6 mi / 7.5 km)
How to get there

Transportation to and around Pleasantville

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 6.1 mi (9.9 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Danbury, CT (DXR-Danbury Municipal), which is 23.3 mi (37.5 km) away.

How many vacation rentals are available around Pleasantville, NY?

Our 2020 property listings offer a large selection of 86 vacation rentals around Pleasantville. From 59 house rentals to 11 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a water-view property in Pleasantville?

The soothing sounds, the undeniable stillness, the mesmerizing views... is there anything more pleasurable than being at the water's edge? Vrbo has 8 vacation rentals with waterfront views in this destination. Of course, that might not work for the whole group. Fortunately, Vrbo has a bunch more options, including:

  • 8 city-center vacation rentals.
  • 7 village vacation rentals.
  • 5 mountain-view vacation rentals.

Can I rent a house in Pleasantville?

Forget about uninspiring hotel-chain rooms. Our house vacation rentals each have their own unique personalities — and all the space you could possibly need! There are 58 options listed on Vrbo. Prices start at $95 a night. Or maybe you'd rather pick one of the area's other popular rental types, like:

  • Hotel: 34 vacation homes. Prices start from $90 per night.
  • Apartment: 9 vacation homes. Prices start from $174 per night.
  • Townhome: 4 vacation homes. Prices start from $226 per night.

Can I stay in Pleasantville in a large group?

There's nothing quite like being somewhere new with close friends and family. And the great news is Vrbo has options suitable for big groups. House vacation homes are the leading choice for big groups of guests, with 9 available here. Properties in this area that are perfect for large groups include:

  • If yours is a party of 6, we have 15 vacation homes appropriate for that size. Stay a night for as little as $110.
  • If you have 5 in your group, you'll be pleased to hear that there are 12 vacation homes perfect. The starting price is $139 a night.
  • Looking for properties for rent catering to 8 guests? You'll be pleased to hear we have 11 that'll be perfect. You can secure one for as little as $600 a night.

So don't fret! When you book with us you can take your dad, your grandpa and all your friends to Pleasantville.

Where are the cheapest rentals in Pleasantville?

Pint-sized hotel rooms are no place to spend those precious vacation moments! Discover our budget-friendly rentals today and make sure everyone in your group has enough room to spread out. Ludlow is an awesome area to consider if you want to keep an eye on your budget. Vrbo has 2 rentals, and the average price is a very agreeable $136 per night. Another 5 Vrbo rentals are available in or around Cove - East Side - Shippan. With an average price of $169 a night, you're sure to grab a deal worth bragging to your friends about.

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