Pleasant Square Vacation Rentals

Discover Your Perfect Pleasant Square Vacation Homes

Best Vacation Homes in Pleasant Square

Best Vacation Homes in Pleasant Square

House

Beautiful Brand New Private Duplex Unit in Lower Hudson Valley "Stone Haven"

10.0

Exceptional

(13 Reviews)

1 Bedroom 1 Bath 5 Guests

US $439/Night 7 Nights - US $3,070

View Deal

Hudson River Views: Briarcliff Manor Home w/Deck

House

Hudson River Views: Briarcliff Manor Home w/Deck

10.0

Exceptional

(2 Reviews)

4 Bedrooms 6 Baths 12 Guests 4154.87 ft²

US $1,361/Night 7 Nights - US $9,527

View Deal

Ossining Vacation Rental Near River, Trails & Mta!

Cottage

Ossining Vacation Rental Near River, Trails & Mta!

1 Bedroom 1 Bath

US $882/Night 7 Nights - US $6,177

View Deal

Cottage

Summer fun on the river. Swim, fish, kayak and bird watch at Croton River Gorge.

9.8

Exceptional

(21 Reviews)

1 Bedroom 1 Bath 4 Guests

US $376/Night 7 Nights - US $2,630

View Deal

NYC-Area Escape Near River, Trails & MTA!

House

NYC-Area Escape Near River, Trails & MTA!

8.7

Fabulous

(3 Reviews)

5 Bedrooms 4 Baths 11 Guests 2798.62 ft²

US $689/Night 7 Nights - US $4,825

View Deal

House

Summer Pool Oasis Custom Bar Arcade Pool Table

1 Bedroom 1 Bath

US $1,525/Night 7 Nights - US $10,676

View Deal

Highly Rated

House

Cozy house on the Hudson

9.6

Exceptional

(73 Reviews)

1 Bedroom 1 Bath 2 Guests

US $409/Night 7 Nights - US $2,861

View Deal

Hotel

Windrose on Hudson

7.1

Very Good

(57 Reviews)

4 Baths 215.28 ft²

US $284/Night 7 Nights - US $1,989

View Deal

Hotel

Windrose On Hudson

8.6

Fabulous

(210 Reviews)

1 Bath

US $230/Night 7 Nights - US $1,607

View Deal

Polished 1BR w/Accessible Room Features + Sauna

Price Dropped

Apartment

Polished 1BR w/Accessible Room Features + Sauna

6.0

Good

(1 Review)

1 Bedroom 1 Bath 2 Guests 210 ft²

US $292/Night 7 Nights - US $2,041

View Deal

House

Near NYC! | Stylish Guestroom

1 Bedroom 1 Bath 4 Guests 210 ft²

US $341/Night 7 Nights - US $2,386

View Deal

1BR Queen near NYC | Trails, Biking & Sauna Bliss

Price Dropped

Apartment

1BR Queen near NYC | Trails, Biking & Sauna Bliss

1 Bedroom 1 Bath 2 Guests 210 ft²

US $263/Night 7 Nights - US $1,840

View Deal

See More Pleasant Square Vacation Rentals

Why Choose Rent By Owner for your Pleasant Square Vacation Rental Homes?

What makes our Vacation Rentals special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Pleasant Square Vacation Rentals

Where are the best neighborhoods to stay in Pleasant Square?

Discover the charm of Pleasant Square, Ossining, New York, a welcoming neighborhood that offers a peaceful retreat while being conveniently close to local amenities. When booking your vacation rental in this area, you'll enjoy easy access to the scenic surroundings and the authentic atmosphere that makes Ossining unique. Whether you’re seeking a relaxing escape or an adventure-filled getaway, choosing accommodation in Pleasant Square provides a comfortable base to explore all that this delightful part of New York has to offer.

Highlands

This neighborhood offers a tranquil setting with convenient access to the surrounding region, making it an ideal choice for those seeking peaceful surroundings near Pleasant Square. You'll find it offers a blend of quiet streets and easy connectivity to explore the area comfortably.

View 179+ Rentals in Highlands

Northeast Yonkers

Located just a short drive from here, Northeast Yonkers provides a vibrant community atmosphere with close proximity to local amenities and outdoor spaces, perfect for travelers looking for convenience combined with a lively neighborhood vibe.

View 180+ Rentals in Northeast Yonkers

North Stamford

A charming area just across the border, North Stamford is known for its scenic views and welcoming ambiance, offering a peaceful retreat while still being easily accessible to enjoy the attractions of the region.

View 283+ Rentals in North Stamford

Best Times to Visit Pleasant Square

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, as the weather and local events in Pleasant Square, Ossining, New York, influence the best periods for vacation rentals in this region.

Peak Season Highlights

Late Spring to Early Summer (May to June)

During these months, you will experience pleasant weather ideal for outdoor activities and exploring the region's scenic beauty.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F

Early Autumn (September to October)

This period offers cooler temperatures and fewer crowds, making it a perfect time to enjoy the area's tranquil atmosphere and natural surroundings.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F

Off-Season Highlights

Winter (December to February)

Visit here during the winter months to experience quieter streets and lower rates on vacation rentals, though you'll want to be prepared for colder weather.

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

Late Fall (November)

This is a less busy time, with the landscape transitioning to winter. It provides a peaceful retreat with more affordable vacation rental options.

Average Temperature Daytime: 45-55°F - Nighttime: 35-45°F

Weekly Weather Forecast for Pleasant Square

How to Book Your Pleasant Square Vacation Rental Home

What's our booking process?

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

Booking Steps

Search Properties

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

Select a Rental

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

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 Vacation Rentals in Pleasant Square Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 a spacious outdoor patio or deck for relaxing and entertaining in the fresh air.
Take advantage of a private backyard perfect for outdoor dining or casual gatherings.
Make use of a well-maintained garden area to enjoy the natural beauty of the region.
Benefit from convenient parking options for easy access during your stay.
Explore nearby walking trails or outdoor paths ideal for leisurely strolls or jogging.
Relax by an outdoor seating area designed for enjoying the sunset views of the surrounding area.
Utilize outdoor grilling facilities to prepare local cuisine with ease and convenience.

Top Attractions Around Pleasant Square

What attractions are nearby?

In this charming region, you can explore scenic parks, enjoy local cultural attractions, and experience outdoor activities that highlight the natural beauty of the surrounding area.

Family Activities

Ossining Historical Society Museum: Explore local history and engage young minds with interactive exhibits that highlight the area's rich heritage.
: Enjoy family-friendly walks along scenic trails, perfect for picnics and outdoor adventures in this tranquil park setting.
Hudson River Waterfront Walkway: Take a leisurely stroll along the river, where scenic views and gentle breezes create an ideal atmosphere for quality family time.
Sing Sing Kill Green: Relax and unwind in this peaceful green space offering open areas for play, making it a popular spot for families in the region.

Adult Activities

Exploring the Ossining Farmers Market: Immerse yourself in local flavors and fresh produce by visiting this vibrant market nestled within the region, perfect for a leisurely morning.
Walking Along the Historic Main Street: Discover charming shops, cafes, and architectural gems on a stroll down this welcoming street that showcases the area's rich history and community spirit.
Enjoying a Riverside Picnic at Ossining Riverfront Park: Relax with scenic views and gentle breezes by the water while savoring a picnic in this peaceful outdoor setting here.
Attending Cultural Events at the Ossining Arts Center: Engage with local arts and performances that highlight the region's creative spirit, offering enriching experiences for visitors seeking entertainment and inspiration.

Pleasant Square Travel Tips

How Can You Make the Most of Your Stay?

Explore Local Dining and Markets: Take advantage of the region’s culinary scene by visiting local eateries and markets to experience authentic flavors and support small businesses during your stay.
Plan Outdoor Activities: Make the most of outdoor pursuits like walking or cycling along scenic trails, which showcase the natural beauty of this destination’s surroundings.
Visit Nearby Attractions: Discover nearby cultural or historical sites that enrich your understanding of the area's heritage and provide memorable excursions from your rental.
Coordinate with Your Rental Host: Communicate with your host beforehand to gain insider tips on hidden gems and the best times to visit popular spots in this region.

Transportation Options

Metro-North Railroad: You can conveniently access commuter train services that connect directly to New York City and other regional destinations from nearby stations, making travel to and from this area straightforward.
Local Bus Services: Local transit buses provide flexible transportation options around the region, ideal for exploring Pleasant Square and its surroundings without the need for a car.
Driving and Car Rentals: Renting a car or using your own vehicle allows you to explore the area at your own pace, offering easy access to scenic routes and neighboring attractions in this part of Westchester County.
Taxi and Rideshare Services: Taxis and rideshare options such as Uber and Lyft are readily available for quick, comfortable trips within the area or to nearby towns and transportation hubs.

Local Customs Options

Community Celebrations: Participating in local festivals and parades showcases the region's vibrant community spirit, offering a glimpse into its cultural heritage.
Historical Respect: Respect for historic sites and traditions is a valued custom here, reflecting the area's appreciation for its rich past.
Local Art Appreciation: Supporting local artists and their crafts during markets and exhibits helps keep the region's artistic traditions alive.
Environmental Stewardship: Embracing eco-friendly practices, such as recycling and conservation, aligns with the area's commitment to preserving its scenic beauty.

Pleasant Square Vacation Rental Frequently Asked Questions

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 2026 is over 46 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 vacation rentals in this area?

Cancellation policies vary depending on the individual property's terms. You should review the specific listing details or contact the property owner directly to understand the cancellation options and any applicable fees.

4. How do I book a vacation rental in Pleasant Square, Ossining, New York?

You can reserve your stay by selecting your preferred dates on the listing page and completing the booking process online. For additional assistance or special requests, reaching out to the host directly can ensure a smooth reservation experience.

5. Are there any minimum stay requirements in this destination?

Minimum stay requirements are set by each property owner and can differ between rentals. Check the listing description for specific policies or contact the host for clarification before making your reservation.

6. What amenities are typically included in vacation rentals here?

Most vacation rentals in the region offer a range of amenities such as Wi-Fi, fully equipped kitchens, parking, and outdoor spaces. To confirm the features available at a particular property, review the listing details or ask the owner directly.

7. Is it possible to get late check-in or early check-out in these vacation rentals?

Late check-in and early check-out arrangements depend on the individual property’s policies. Contact the property owner ahead of time to discuss your arrival and departure times to ensure accommodation for your schedule.