Discover Your Perfect Pleasant Square Rentals by Owner

Pleasant Square Rentals by Owner

More Top-Rated Rentals by Owner in Pleasant Square Area

Why Choose Rent By Owner for your Pleasant Square vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Pleasant Square Rentals by Owner

Where are the best neighborhoods to stay in Pleasant Square?

When choosing a neighborhood to stay in within Pleasant Square, Ossining, New York, you'll find a variety of charming areas that offer both comfort and convenience. Each neighborhood provides unique opportunities to experience the local charm while enjoying easy access to the vibrant surroundings of Ossining. Whether you're seeking a peaceful retreat or a lively community atmosphere, renting by owner in these neighborhoods ensures a reliable and seamless booking experience. Discover the perfect spot to relax and explore while benefiting from trusted accommodations in this inviting part of Westchester County.

Highlands

Located nearby, Highlands offers a serene atmosphere ideal for travelers seeking quiet surroundings while exploring the local area. You can enjoy the peaceful environment and conveniently access nearby attractions through comfortable rental options.

View 109+ Rentals in Highlands

Northeast Yonkers

This neighborhood provides a lively setting with easy access to the region's amenities, making it perfect for those looking for convenient transportation options and vibrant community experiences.

View 122+ Rentals in Northeast Yonkers

Best Times to Visit Pleasant Square

When should you plan your Rentals by Owner stay?

Choosing the ideal time to vacation here can enhance your experience, as understanding seasonal patterns and local climate conditions will help you select the best period for exploring the region's unique charm through a rental by owner.

Peak Season Highlights

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Spring (March to May)

During this time, you can enjoy the region's pleasant weather and blooming landscapes, making it ideal for outdoor activities and exploring local charms.

Average Temperature Daytime: 55°F to 70°F - Nighttime: 40°F to 50°F
autumn
Fall (September to November)

The fall months bring vibrant foliage and cooler temperatures, providing a picturesque setting for your stay and outdoor adventures in the area.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Summer (June to August)

While summer offers warm weather perfect for enjoying the outdoors, it can also bring higher occupancy rates and increased demand for rentals.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
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Winter (December to February)

This quieter period features colder temperatures that are ideal if you prefer a more peaceful retreat away from peak tourist crowds in the region.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F

Weekly Weather Forecast for Pleasant Square

How to Book Your Pleasant Square vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Pleasant Square

More Top-Rated Rentals by Owner in Pleasant Square Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining with a private patio or picnic area to savor meals al fresco.
  • Take advantage of a spacious backyard perfect for relaxing, playing, or outdoor entertaining.
  • Make the most of scenic views and fresh air with a furnished balcony or veranda.
  • Explore nearby walking trails or nature paths that showcase the natural beauty of the region.
  • Cool off in a private swimming pool or access community pools available in the area.
  • Utilize barbecue grills for family cookouts amidst the picturesque surroundings.
  • Benefit from outdoor fire pits or fireplaces to enjoy cozy evenings under the stars.

Top Attractions Around Pleasant Square

What attractions are nearby?

Within this charming area, you can enjoy a variety of outdoor activities and local attractions that showcase the scenic beauty and cultural heritage of the region, making your stay truly memorable.

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Family Activities

  • Ossining Waterfront Park: Spend a relaxing day outdoors along the Hudson River, where picnicking, playgrounds, and scenic views make it perfect for family outings in the area.
  • Teatown Lake Reservation: Enjoy exploring miles of hiking trails, wildlife viewing, and educational programs designed to engage children and adults alike here in the region.
  • Briarcliff Manor Park: This local park offers sports facilities, open fields, and a playground, providing various activities suitable for the whole family during your stay.
  • Historic Ossining Museum & Historic Site: Discover the area's rich history with interactive exhibits and guided tours that appeal to curious minds of all ages here in this destination.
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Adult Activities

  • Visit the Ossining Historical Museum: Explore local history and heritage in this fascinating museum, offering insightful exhibits just minutes from your rental.
  • Enjoy a scenic walk along the Old Croton Aqueduct Trail: Experience outdoor leisure on this picturesque trail that showcases the area's natural beauty and historical significance.
  • Attend a performance at the Ossining Performing Arts Center: Immerse yourself in arts and entertainment with live shows and events hosted in the region’s vibrant cultural scene.
  • Relax at Louis Engel Waterfront Park: Unwind by the river with peaceful views and recreational activities, perfect for a leisurely day here in the area.

Pleasant Square Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take advantage of the area’s charming eateries to experience authentic regional flavors during your stay.
  • Visit Nearby Natural Spots: Discover the region’s scenic parks and outdoor spaces to enjoy relaxing walks and picturesque views.
  • Connect with the Community: Engage in local events or visit community spots to immerse yourself in the area's culture and hospitality.
  • Plan Your Transportation: Ensure seamless travel by arranging convenient transportation options tailored to this destination’s infrastructure.

Transportation Options

  • Ossining Train Station: This station offers convenient commuter rail services connecting you to New York City and nearby regions, making travel seamless for visitors staying in the area.
  • Local Bus Services: Regional bus routes provide reliable transportation throughout Pleasant Square and surrounding neighborhoods, perfect for exploring without a car.
  • Rental Car Agencies: Numerous rental car providers are available nearby, offering flexibility for those who prefer to explore the region at their own pace.
  • Taxis and Ride-Sharing: Readily accessible taxis and ride-sharing options like Uber and Lyft offer quick and comfortable transportation right from your accommodation here.

Local Customs Options

  • Respect for Local Heritage: You’ll find that honoring the area's historical sites and traditions is an important aspect of daily life here in Pleasant Square, fostering a deep appreciation for the region's cultural roots.
  • Community Celebrations: Participating in local festivals and events allows you to connect with residents and experience the vibrant spirit that defines this destination.
  • Dining Etiquette: The region's culinary customs emphasize friendliness and conversation, making your dining experiences here warm and memorable.
  • Environmental Consciousness: Embracing sustainable practices such as recycling and conservation aligns with the community’s commitment to preserving the natural beauty of this area.

Frequently Asked Questions About Pleasant Square Rentals by Owner

1. What are the top vacation rentals in Pleasant Square?

There are a lot of options in Pleasant Square. If you plan on staying in the Pleasant Square area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pleasant Square:

2. How many Rentbyowner vacation rentals are available in Pleasant Square?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 70 in the Pleasant Square area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pleasant Square. 

3. What is the cancellation policy for renting a property in this area?

The cancellation policy varies by property owner, so it's important to review the specific listing details or contact the host directly to understand the terms and any potential fees involved.

4. How do I verify the safety and cleanliness standards of a rental by owner here?

Each rental listing provides information about the safety measures and cleaning protocols implemented by the owner. You can also reach out to the host for additional details to ensure your comfort and security.

5. Are there any specific check-in or check-out procedures I should be aware of in this destination?

Check-in and check-out procedures are outlined within each property listing. For further clarification or special requests, contacting the owner directly will help ensure a smooth arrival and departure.

6. What amenities are typically included in rentals by owner in this region?

Amenities vary by property but generally include essentials such as Wi-Fi, kitchen access, and parking. To confirm what's available during your stay, refer to the specific listing details or communicate directly with the owner.

7. How do I contact the property owner if I have questions or need assistance during my stay?

Contact information is provided on each rental listing. You can send a message through the booking platform or use the contact details shared by the owner to receive support before or during your visit.

More Rentals You May Like Near Pleasant Square

More Top-Rated Rentals by Owner in Pleasant Square Area