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Discover Your Perfect Pickering Rentals by Owner

Pickering Rentals by Owner

3.1 (8 Reviews)
House
SHAY-BASEMENT-Holiday Home
  • Air Conditioner
  • Parking
  • Security/Safety
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More Top-Rated Rentals by Owner in Pickering Area

Why Choose Rent By Owner for your Pickering 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 Pickering Rentals by Owner

Where are the best neighborhoods to stay in Pickering?

When choosing where to stay in Pickering, Ontario, exploring the various neighborhoods can help you find the perfect rental by owner for your needs. Each area offers a unique atmosphere, whether you're seeking quiet residential streets or convenient access to local amenities. By selecting accommodations within these welcoming communities, you can enjoy an authentic experience of Pickering while benefiting from the reliable and seamless booking process provided by Rent By Owner. Discover the ideal neighborhood that suits your travel style and makes your visit to Pickering memorable and comfortable.

Scarborough

Located just a short drive from Pickering, this area offers convenient access to both urban amenities and natural scenic spots. Here, you can enjoy a comfortable stay that seamlessly blends city convenience with nearby outdoor recreation.

View 257+ Rentals in Scarborough

Best Times to Visit Pickering

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here ensures you experience the best of what the area has to offer, allowing you to plan ahead and secure your ideal rental through Rent By Owner for a seamless stay in Pickering, Ontario, Canada.

Peak Season Highlights

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Summer (June to August)

During the warmest months, you'll experience the peak season when visiting Pickering, Ontario. This is the ideal time for outdoor activities and enjoying the region's natural beauty.

Average Temperature Daytime: around 25°C - Nighttime: around 15°C
autumn
Fall (September to November)

This period marks another popular season with colorful foliage attracting travelers seeking scenic views in the region. It's a great time for exploring and relaxing in your rental.

Average Temperature Daytime: around 18°C - Nighttime: around 8°C

Off-Season Highlights

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Winter (December to February)

The colder months see fewer visitors, making it an ideal time for those looking for quieter accommodations in this destination. Winter offers a different charm for your stay.

Average Temperature Daytime: -2°C - Nighttime: -10°C
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Spring (March to May)

Early spring features milder weather and less crowded attractions, providing a peaceful setting to enjoy your rental here as nature begins to bloom.

Average Temperature Daytime: around 10°C - Nighttime: around 3°C

Weekly Weather Forecast for Pickering

How to Book Your Pickering 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 Pickering

More Top-Rated Rentals by Owner in Pickering 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

  • You can enjoy spacious outdoor patios or decks to relax and dine al fresco amid scenic surroundings.
  • Expect well-maintained gardens or landscaped yards that provide a peaceful setting for outdoor activities.
  • Many rentals offer private or community swimming pools for refreshing dips during warm days.
  • Look for outdoor grilling areas or BBQ facilities to prepare your favorite meals while enjoying the fresh air.
  • Some properties feature outdoor fire pits or fireplaces perfect for cozy evenings under the stars.
  • Community tennis courts, basketball hoops, or nearby parks allow you to stay active during your stay.
  • Enjoy access to outdoor recreational spaces such as walking trails or nature preserves in the region.

Top Attractions Around Pickering

What attractions are nearby?

Within this vibrant region, you can explore a variety of outdoor activities and scenic spots that offer a perfect blend of relaxation and adventure, making it an ideal choice for your stay in Pickering, Ontario, Canada.

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Family Activities

  • Pickering Museum Village: Step back in time by exploring this historical site, perfect for family members interested in local history and interactive learning experiences.
  • Enjoy a day outdoors with your loved ones in this expansive national park, offering scenic trails, wildlife viewing, and nature walks suitable for all ages.
  • Bay Ridges Park: Relax and play at this popular waterfront park with picnic areas, playgrounds, and beautiful views of Lake Ontario, ideal for family outings in the area.
  • O'Brien Park: Engage in recreational activities and sports at this family-friendly park featuring sports fields, walking paths, and open spaces perfect for quality time together.
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Adult Activities

  • Pickering Museum Village: Step back in time at this historic village, where you can explore authentic exhibits and enjoy interactive demonstrations that bring the region's history to life.
  • Rouge National Urban Park: Experience outdoor adventures in Canada’s first national urban park, offering scenic trails, wildlife viewing, and a peaceful escape within the area.
  • Lake Ontario Waterfront Trail: Take a leisurely walk or bike ride along this picturesque waterfront trail, perfect for enjoying panoramic views of the lake and relaxing by the water.
  • Pickering Golf Club: Improve your swing at this well-maintained golf course, providing a challenging yet enjoyable experience amidst the natural beauty of the region.

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Pickering Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead and Book Early: Secure your rental in advance to access the best options and ensure availability during peak travel seasons in this popular destination.
  • Explore Local Amenities: Make use of nearby shops, restaurants, and facilities to enjoy a truly authentic experience while staying comfortable and well-equipped here.
  • Respect Community Guidelines: Familiarize yourself with local rules and property policies to have a smooth stay and contribute positively to the area’s welcoming atmosphere.
  • Embrace the Surroundings: Take time to enjoy the natural beauty and scenic spots nearby, enriching your visit and making the most of your time in this region.

Transportation Options

  • Pickering Transit Service: You can conveniently access local bus routes within the area, making it easy to explore here without a car.
  • GO Transit Rail Service: The regional rail connections provide quick and reliable transportation to Toronto and other parts of Ontario, ideal for day trips or commutes.
  • Toronto Pearson International Airport: This major airport nearby offers numerous domestic and international flights, perfect for travelers arriving from afar.
  • Private Car Services & Taxis: Reliable taxi and ride-sharing options are available here, providing flexible transport for all your travel needs around the region.

Local Customs Options

  • Community Events and Festivals: Throughout the year, you can participate in local events that celebrate the area's rich cultural heritage and community spirit.
  • Respect for Nature and Parks: Environmental conservation is valued here, so be mindful of preserving the natural beauty when visiting parks or outdoor spaces.
  • Local Indigenous Heritage: Honoring the area’s indigenous history, you’ll find traditions and art displayed with respect during your stay.
  • Dining Etiquette and Local Cuisine: Embracing regional flavors and customs, enjoy the region's culinary offerings with an appreciation for local dining practices.

Frequently Asked Questions About Pickering Rentals by Owner

1. What are the top vacation rentals in Pickering?

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

2. How many Rentbyowner vacation rentals are available in Pickering?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 220 in the Pickering 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 Pickering. 

3. How do I find the cancellation policy for a rental by owner in Pickering, Ontario?

The cancellation policy is typically detailed on the property's listing page. To ensure you understand the specific terms, review the stated policy or contact the owner directly for clarification before completing your booking.

4. What should I know about checking in and check-out times for rentals in the area?

Check-in and check-out times are usually specified in the listing details. To facilitate a smooth arrival and departure, verify these times with the owner prior to your stay, especially if you have special scheduling needs.

5. Are pet accommodations available at property rentals near Pickering, Ontario?

Pet policies vary by individual owner and property. It's best to read the listing carefully for any mention of pet allowances or restrictions, or contact the owner directly to confirm if your pets can stay with you.

6. How can I ensure my booking is protected when reserving directly with an owner in this region?

Booking through the Rent By Owner platform offers a layer of security and trust. Always use the platform’s messaging system to communicate with the owner, and review the listing's reviews and ratings before finalizing your reservation.

7. What amenities are commonly included in rentals by owner in this destination?

Amenities vary by property, but typical features include Wi-Fi, parking, kitchen facilities, and laundry. For a comprehensive list of what's included, check the individual listing details or ask the owner directly to ensure your needs are met.

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More Top-Rated Rentals by Owner in Pickering Area