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Pickering vacation rentals

We found 391 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of 33 homes, 12 apartments, and other vacation rentals in Pickering that are perfect for your trip. Vacation homes offer the amenities you expect for your stay with friends, family, or just your pet, such as WiFi and a fireplace. At the end of the day, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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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.

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.

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.

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.

Transportation options to and around Pickering

The nearest airport is in Toronto Pearson Intl. Airport (YYZ), located 28.3 mi (45.6 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Billy Bishop Toronto City Airport (YTZ), which is 21 mi (33.8 km) away.

Catch a ride on the metro at Pickering Station for ease of access to the rest of the city.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Pickering?

The most desirable types of vacation rentals in Pickering are houses. Prefer something different? Vrbo has numerous options to match the unique needs of our guests, so you'll see vacation properties in all shapes and sizes. The perfect fit is waiting for you — get hold of yours today.

How much does it cost to rent a vacation rental in Pickering?

Different factors determine how much you'll pay for a vacation rental in Pickering, including the time of year, length of stay and property type. However, all our vacation homes have one thing in common — incredible value. Simply add your travel dates to find your ideal match.

How much does it cost to rent a beach house in Pickering?

Prices for beach houses in Pickering vary depending on the type and size of the property and time of year you're traveling. Just enter your travel dates into Vrbo and the number of guests to see available options and prices. From there you can use the filters to narrow your search by ratings, amenities, nearby activities and more.

Are there pet-friendly vacation rentals in Pickering?

There are, yes. Take your pick of 14 vacation homes that welcome pets in Pickering on Vrbo. Our cuddly best friends need a getaway too, so simply use our search function for pet-friendly vacation rentals to find a property where Fido can share in the good times.

Can I rent a house with a pool in Pickering?

Check the "pool" box in our filter tool and choose from two houses with private pools in Pickering on Vrbo. Ball games, gentle soak or noodle joust? Free time is up to you when your Vrbo vacation property comes with its own pool.

What are popular rental amenities in Pickering?

The most popular rental amenities people are searching for in Pickering are a firepit, a nearby waterfront and a swimming pool. Whether you're taking a trip with family, friends or even pets, Vrbo vacation properties have the best amenities for making epic memories with the people that matter most.

Are there vacation rentals in Pickering that welcome kids?

With 14 family-friendly vacation rentals available in Pickering, now is a fantastic time to introduce the kids to the thrills of travel. Simply click on our "Properties good for families" filter to search for stays packed with amenities perfect for vacationing families, like kitchens, pools, entertainment units and bunk beds.

What are the top attractions for families in Pickering?

Keep the kids busy at these top family-friendly attractions in Pickering:

  • Whitby History Museum & Childrens Centre
  • Lynde Shores Conservation Area
  • Deer Creek North Golf Course

Are there one-bedroom vacation rentals in Pickering?

Yes, there are four one-bedroom properties in Pickering to pick from. A one-bedroom vacation home is a wonderful option if it's just two of you or if you're traveling alone. Add in more privacy, space and convenience than a regular hotel, and you're sure to have an unforgettable trip.

Can I find two-bedroom vacation rentals in Pickering?

Take your pick of four two-bedroom vacation properties in Pickering. Put your little ones in the second room or maybe fill it with a couple of your nearest and dearest friends. There's ample space for whoever's lucky enough to be coming along.

Are there vacation rentals with WiFi in Pickering?

You can choose from 11 vacation rentals with WiFi in Pickering. If you want to disconnect from the world on your break, but still want to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Pickering?

You can choose from 13 vacation rentals with air conditioning in Pickering giving you that cool, cool breeze and extra bit of comfort. Enter your preferred travel dates and then use our filters to locate stays with air conditioning.

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