1. Canada
  2. Ontario
  3. Oshawa
  4. Pickering
  5. Holiday Homes

229+ Pickering Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Pickering

Discover more than 229 treehouse rentals in Pickering, perfect for your holiday adventure. Treehouse offers treetop accommodations with everything you need for a relaxing escape near Pickering, ON.

Whether you're seeking luxury multi-level treehouses, rustic forest cabins, cozy off-grid retreats, or family-friendly treehouse lodgings, we can help you find the ideal place. Our rentals feature top-notch amenities such as private decks, fully equipped kitchens, fire pits, hot tubs, and Wi-Fi, ensuring your group enjoys a comfortable and memorable stay.

Planning a group getaway to Pickering? TreeHouse guarantees a unique and unforgettable experience with plenty of options for families, large groups, or private rentals for long or short stays. Explore our Pickering pet-friendly treehouse rentals and easily book your dream treehouse vacation rental in Pickering with TreeHouse.

Show more
Show less

Frequently Asked Questions About Pickering Holiday Rentals

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 Holiday Home Rentals in Pickering:

There are many holiday rentals available in Pickering; however, here are a few of the most popular holiday homes listed in Pickering on our website:
At Treehouse Rentals most of our places to stay are perfect for families. Check out the complete list of holiday homes in Pickering to find one that works for you.
Yes, there are 229 self-catering family homes and holiday rentals in Pickering.
There are more than 229 luxury holiday homes in or near Pickering, according to 2025 data from Treehouse Rentals. Consider these homes for your next holiday:
Yes, there are 229 pet friendly rentals that are available in Pickering.