Pleasantville holiday rentals

We found 199 holiday rentals — enter your dates for availability
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.

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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 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)
  • Hand & Stone Massage and Facial Spa (13.6 mi / 21.8 km)
  • New York Country Club (13.6 mi / 21.8 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)
  • Croton Point Park (6.3 mi / 10.1 km)
  • Nyack Beach State Park (6.3 mi / 10.1 km)
  • Silver Lake Park (6.5 mi / 10.5 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

What is the best area to stay in Pleasantville when booking a holiday rental?
When considering a holiday rental in Pleasantville, New York, the area surrounding the charming village centre is highly recommended. This neighbourhood boasts a delightful mix of quaint shops, cafes, and eateries, creating a vibrant setting that is superb for leisurely strolls. A key attraction in this area is the historic Jacob Burns Film Centre, which offers a variety of independent and classic films, making it a cultural hub for cinema enthusiasts. Additionally, the nearby Rockefeller State Park Preserve provides a beautiful natural setting, ideal for hiking and outdoor activities, with its expansive trails and picturesque landscapes.The village centre offers a range of properties, from cosy cottages to more spacious family homes, suiting different preferences and group sizes. Staying here not only places you in the heart of Pleasantville's charm but also grants easy access to local attractions, enhancing your overall holiday experience.
What is the most popular type of holiday rental accomodation in Pleasantville?
In Pleasantville, cottages are the most popular type of holiday rental, with several available throughout the charming neighbourhood. These cottages typically provide a cosy atmosphere, featuring fully equipped kitchens for self-catering, comfortable living areas for relaxation, and often outdoor spaces such as gardens or patios for enjoying the fresh air. The town's quaint setting, along with easy access to local parks and shops, makes these rentals particularly appealing for those looking to unwind in a peaceful environment.
What are popular rental amenities in Pleasantville?
In Pleasantville, popular rental amenities include air conditioning, which is essential for ensuring comfort during the warmer months. Holiday rentals in the area typically feature this amenity to help guests relax after a day of exploring local attractions such as the Jacob Burns Film Centre and the charming downtown area with its shops and restaurants.
When is the best time to visit Pleasantville for a holiday rental?
The best time to visit Pleasantville for a holiday rental is during the peak season from June to August, with July being particularly popular among travellers. This vibrant summer period sees a flurry of activity, with many visitors drawn to the charming village atmosphere and the beautiful surroundings of Westchester County.During these months, Pleasantville boasts warm temperatures averaging between 20 to 30 degrees Celsius, making it ideal for outdoor activities. You can enjoy leisurely strolls through the local parks, visit the farmers' market, or take part in community events that showcase the area's rich culture. The pleasant weather enhances the experience, allowing for comfortable sightseeing and exploration of nearby attractions.If you are seeking a more affordable time to visit, consider December. While this month falls into the low season, it offers a unique charm with holiday festivities and a quieter atmosphere that can be appealing for those looking to unwind.Ultimately, your choice hinges on whether you prefer the lively summer vibe with plenty of activities or the peaceful charm of winter festivities.
What are the top attractions in Pleasantville?
In Pleasantville, visitors can explore a charming blend of nature and culture. The village is known for its picturesque downtown area, which features a variety of local shops, cafes, and restaurants that create a friendly setting. The Jacob Burns Film Centre is a highlight, offering independent and classic films, along with engaging community events and discussions.For those who appreciate the outdoors, the nearby Rockefeller State Park Preserve is a fantastic destination, featuring miles of scenic trails superb for hiking and enjoying the natural landscape. The area also hosts the annual Pleasantville Music Festival, attracting numerous visitors with its lively performances and family-friendly activities.
Are all fees included in the Pleasantville holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Pleasantville holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pleasantville with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Pleasantville holiday homes?
You can find great discounts on holiday homes in Pleasantville on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Pleasantville holiday home booking on Stayz?
To find Pleasantville holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pleasantville?
A long-stay holiday home in Pleasantville is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pleasantville holiday home?
Book your Pleasantville holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pleasantville?
Prices for holiday homes in Pleasantville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pleasantville to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.