Pickering, ON, Canada

Pickering, ON, Canada

We found 144 vacation rentals — enter your dates for availability


Find the best place to stay — Pickering

Where to stay near Pickering, CA?

Our 2018 property listings offer a large selection of 144 vacation rentals near Pickering. From 88 houses to 23 apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Pickering for a holiday or a weekend are on HomeAway.

Lose track of time in the waterfront city of Pickering

Located just 30 minutes outside of Toronto, Pickering offers a tempting opportunity to escape the hustle and bustle of big city life and enjoy a little downtime with family and friends. Discover the charm of this community as you explore the miles of colorful trails that trace the shoreline of Lake Ontario or peek into the area’s past at the fascinating Pickering Museum Village. Pickering vacation rentals can be a great way to enjoy a little more space during your stay while putting you right on the doorstep of all that this beautiful waterfront getaway has to offer.

Explore Lake Ontario from Pickering

There are few finer places to enjoy the great outdoors than Pickering and, as you might imagine, lots of the action takes place on or at least near the water. Lake Ontario provides the perfect setting for kiteboarding and surfing, although if you’d prefer to stay dry, boat cruises from Frenchman’s Bay Marina offer a less energetic means of admiring the breathtaking surroundings. The shoreline also offers cyclists a chance to get in on the action, namely along the 7-mile-long trail that follows the curve of the lake from the Pickering/Ajax border all the way to Scarborough.

Culture abounds in Pickering

A culture fix is easy to come by in Pickering’s lakeside setting. It often comes in the form of live entertainment, perhaps most notably at Pickering Museum Village between June and September, when costumed interpreters will take you on a fascinating tour of 19 heritage buildings. If you have kids in tow, you can learn how to make ice cream while you’re there. The fun continues back in town where lively performances and comfort food at the century-old Herongate Barn Dinner Theatre offer the perfect way to round off your day before heading back to your Pickering vacation rental.

Enjoy sunny days in glorious Pickering

If you like things nice and hot, summer is an excellent time to stay in a Pickering vacation rental. The months of July and August see temperatures soar to around 80 degrees, providing the perfect setting to enjoy the area’s abundance of outdoor activities. Temperatures in spring and fall can be much lower, although indoor attractions such as the Durham West Arts Centre and cozy dining spots in the Nautical Village ensure the area keeps a fist-like grip on its appeal. Winters are cold and wet with temperatures between December and February typically below freezing.

Discover natural attractions near Pickering

Away from the obvious draw of Lake Ontario and its picturesque waterfront and beaches, Pickering has some surprises up its sleeve for outdoor enthusiasts. Along the city’s westerly border, you’ll find the Rouge National Urban Park where 25-square-miles of space encompasses wilderness areas, the Rouge River, and Canada’s largest wetland. The park is well known for its birdwatching prowess, particularly from the vantage points provided by the Vista Trailhead and Glen Eagles Vista, although fishing, swimming, and hiking also feature heavily on the menu. Just a little further afield, several waterfront parks offer the chance to get close to the area’s soaring Scarborough Bluffs.