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Pickering vacation rentals

We found 523 vacation rentals — enter your dates for availability

Discover a selection of 53 homes, 19 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.

Vacation rentals with weekly discounts - Pickering

Showing deals for:Aug 29 - Sep 5
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Find out more about Pickering

Find out more about Pickering

Why visit Pickering

  1. Scenic Waterfront: Enjoy breathtaking views and leisurely strolls along the picturesque Pickering Waterfront.
  2. Vibrant Shopping: Explore a variety of stores and dining options at the bustling Pickering Town Centre.
  3. Family-Friendly Attractions: Discover numerous parks and activities perfect for families of all ages.
  4. Botanical Gardens: Visit beautiful botanical gardens that offer a serene escape into nature.
  5. Cozy Accommodations: Find comfortable vacation rentals, from private homes to convenient apartments.

Popular types of accommodation in Pickering

Planning a getaway to Pickering? Exciting times await as you select your perfect home away from home! Explore our top picks for vacation rentals, including houses, apartments, and condos. Whether you’re seeking cozy house rentals in Pickering or convenient apartment rentals, we have options that cater to your needs. Discover the ideal vacation rental that offers comfort, savings, and a memorable experience.

  • Houses: The top choice for visitors in Pickering, these homes offer spacious accommodations for families and groups, perfect for a home-away-from-home experience.
  • Apartments: A popular option for travelers seeking convenience and easy access to local attractions, apartments provide a cozy and functional stay.
  • Condos: Offering a blend of comfort and amenities, condos are ideal for those wanting a resort-like experience during their trip.
  • Cottages: A charming option that provides a peaceful retreat, perfect for enjoying nature and relaxation.
  • Villas: These upscale residences provide luxurious accommodations, ideal for travelers seeking a lavish getaway.**

Top attractions near Pickering

Pickering, Ontario, is a fantastic destination for city-themed, family, and romantic vacations. Visitors can explore urban parks, modern colleges, and beautiful botanical gardens, offering a mix of outdoor and city experiences. Whether you're traveling with family or looking for a romantic getaway, Pickering has something for everyone. Don't miss the chance to discover all that this charming city has to offer!

  1. University of Toronto Scarborough: This modern campus offers a vibrant city atmosphere, featuring contemporary architecture and lush green spaces. Explore its diverse academic programs and enjoy the lively student life while taking in beautiful views of the surrounding area.
  2. Ajax Convention Centre: Perfect for business travelers, this event venue hosts conferences and meetings in a professional setting. Its modern facilities and convenient location make it an ideal spot for networking and corporate events.
  3. Rouge National Urban Park: A beautiful urban park that blends family-friendly activities with outdoor adventures. Enjoy hiking, picnicking, and observing wildlife in this expansive natural oasis, all while being close to the city.

Things to do recommended for couples

For a romantic getaway in Pickering, consider visiting Skyloft Ski Resort for thrilling outdoor adventures or unwind at Willow Springs Winery for a cozy tasting experience. Earl Bales Ski and Snowboard Centre offers fun skiing options, perfect for couples looking to enjoy some winter sports together.

Things to do recommended for families

Families can enjoy exciting activities in Pickering, including sports at the Markham Pan Am Centre, ice skating at Cedarena, and outdoor fun at Neb's Funworld. These attractions offer vibrant experiences that cater to both adventure and family bonding.

What do I need to keep in mind when booking a vacation in Pickering

If you're traveling with a group, as a family, with pets, or planning an extended stay, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Pickering with a group: Think about how many bedrooms you require, as well as features like a full kitchen or outdoor areas for group activities. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Pickering with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, and to look for amenities that cater to their age, like a private swimming pool. Additionally, keeping in mind how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Pickering: For many families, a vacation wouldn’t be the same without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pickering: If you're in search of vacation rentals offering special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Pickering

Pickering, Ontario, offers a delightful blend of family-friendly attractions and vibrant city life. Explore the picturesque Pickering Waterfront for stunning views or shop at the bustling Pickering Town Centre. This charming city is perfect for romantic getaways or family vacations, providing a warm atmosphere filled with friendly people. Whether you're seeking historical insights or budget-friendly options, Pickering promises a memorable trip with plenty of vacation ideas to explore nearby.

  • Ajax: Ajax is a vibrant city located a mere 3 miles from Pickering, offering visitors a delightful blend of family-friendly activities and urban experiences. The city is known for its bustling shopping mall centers and casinos, making it a popular destination for those seeking entertainment and retail therapy. Ajax is also home to significant landmarks such as sports facilities and a picturesque lake, perfect for leisurely strolls or picnics. With its convenient location and array of attractions, Ajax provides an enjoyable day trip for travelers looking to explore beyond Pickering.
  • Rouge: Situated 5 miles from Pickering, Rouge is a charming neighborhood that invites outdoor enthusiasts and families alike to experience its adventurous spirit. Known for its expansive recreational areas, amusement parks, and sports facilities, Rouge is a perfect spot for those looking to enjoy active pursuits. Visitors can revel in the excitement of local attractions such as waterparks and stadiums, making it an ideal destination for a fun-filled day with loved ones. The natural beauty and recreational opportunities in Rouge ensure that you’ll have a memorable experience during your vacation.
  • Port Union: Port Union, also located 5 miles away from Pickering, is a delightful neighborhood that combines family-friendly activities with outdoor adventures. The area is dotted with shopping centers and recreational spots, providing ample opportunities for relaxation and leisure. Notable landmarks include urban parks and sports facilities, where visitors can enjoy various activities and events. Port Union's inviting atmosphere and diverse attractions make it a fantastic choice for those seeking a mix of urban life and outdoor experiences, ensuring a well-rounded vacation experience.

Best time to go to Pickering

If you're planning a trip to Pickering, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January23.0°F (-5.0°C)Light RainMostly CloudySlightly LowSlightly Low
February23.4°F (-4.8°C)Light RainMostly CloudyAverageSlightly Low
March32.0°F (0.0°C)Light RainMostly CloudyAverageSlightly Low
April42.3°F (5.7°C)Light RainMostly CloudyAverageAverage
May54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
June63.5°F (17.5°C)Light RainMostly SunnySlightly HighSlightly High
July70.2°F (21.2°C)Light RainMostly SunnySlightly HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnySlightly HighSlightly High
September63.3°F (17.4°C)Light RainMostly SunnyAverageAverage
October51.4°F (10.8°C)Light RainMostly SunnyAverageAverage
November39.7°F (4.3°C)Light RainMostly CloudySlightly LowAverage
December30.7°F (-0.7°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to significant price differences. Moreover, extending your stay can often result in even greater savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. It's rewarding to be the planner! By enrolling in our travel rewards program, One Key, you can immediately access member savings and earn OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new trips, pick up where you last stopped, or review and organize your travel plans. You can easily access the properties you've saved and booked, now categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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

How much does it cost to rent a vacation rental in Pickering?
Different factors can determine how much you pay for a vacation rental in Pickering, including the type of property, season and length of stay. But, all of our vacation homes have something in common — amazing value. Simply add your travel dates to find your home away from home.
How much does it cost to rent a beach house in Pickering?
The average price for a vacation home close to the beach in Pickering depends on when you’re traveling and the size and style of property you want. You can easily and quickly find prices on Vrbo by entering your dates of travel. Then use our filter tool to select the number of bedrooms and amenities that you prefer, like WiFi, air conditioning and a hot tub.
How old do you have to be to rent a vacation rental in Pickering?
The minimum required age is normally 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your preferred Pickering vacation home before making a booking.
How long can I rent a vacation rental in Pickering for?
The amount of time you can rent a Pickering vacation home for differs depending on the property. Just tap in your travel dates to browse available options that offer long-term stays. They include all you need to make your extended trip more comfortable and convenient, such as kitchens and backyards. Some vacation homes may also offer weekly or monthly discounts, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Pickering?
In Pickering, you’ll find some great deals and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re off on a weekend getaway or a much longer stay, we’ve got plenty of options to suit your style.

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