Photo by Eric & Kristy's Adventures

Pickering holiday lettings

We found 526 holiday rentals — enter your dates for availability

Discover a selection of 65 homes, 21 apartments and other holiday rentals in Pickering that are perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as a fireplace and garden. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Pickering

Showing deals for:24 Oct - 31 Oct
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Why visit Pickering

  • Charming market town: Discover delightful local shops and eateries in Pickering's quaint town centre.
  • Scenic outdoor spaces: Enjoy picturesque views along the River Humber and from Potter Hill.
  • Family-friendly activities: Engage in various outdoor adventures and attractions suitable for all ages.
  • Botanical gardens: Relax in beautifully maintained gardens, perfect for a tranquil day out.
  • Diverse accommodation: Choose from private homes, apartments, and condos to suit your travel needs.

Popular types of accommodation in Pickering

If you're considering a getaway to Pickering, you'll find a variety of delightful accommodation options. Our most popular choices include houses, apartments, and condos, perfect for every traveller. Whether you're seeking houses for rent in the centre of Pickering or a cosy bedroom flat with easy access to local amenities, we have something to suit your needs. Enjoy the peace of mind that comes with transparent information and great savings on your stay.

  • Houses: The top choice for visitors to Pickering, these homes offer a spacious and comfortable retreat for families or groups seeking a home-away-from-home experience.
  • Apartments: A popular option for solo travellers or couples, apartments provide convenience and proximity to local amenities and attractions.
  • Condos: Ideal for those seeking a modern living space, condos combine comfort with a range of facilities in a community setting.
  • Cottages: These quaint retreats offer a charming, rustic atmosphere, perfect for a peaceful getaway.
  • Villas: For a touch of luxury, villas provide spacious accommodations with elegant surroundings and stunning views.**

Top attractions near Pickering

Pickering, Ontario, offers a delightful mix of experiences perfect for city-themed, family, and romantic getaways. Visitors can explore urban parks, modern colleges and universities, and beautiful botanical gardens. The area's attractions cater to those seeking outdoor adventures, family-friendly activities, and vibrant city experiences, ensuring there's something for everyone to enjoy during their stay.

  • University of Toronto Scarborough: A vibrant and contemporary campus that reflects city life, offering a unique educational atmosphere. Visitors can enjoy its beautiful architecture and engaging community events.
  • Rouge National Urban Park: A stunning urban park perfect for families, offering a blend of outdoor activities and natural beauty. Enjoy hiking trails, wildlife viewing, and picnicking amidst lush landscapes.
  • Ajax Convention Centre: A premier venue for business events and conferences, featuring modern facilities and a professional atmosphere, ideal for networking and corporate gatherings.

Things to do recommended for couples

For a romantic getaway in Pickering, explore the thrilling slopes at Skyloft Ski Resort, just 8.1km away. Enjoy a delightful afternoon at Willow Springs Winery, offering a perfect blend of romance and entertainment, located 8.7km from town. Don't forget the Earl Bales Ski Centre for some sports fun!

Things to do recommended for families

Families can enjoy a variety of activities in Pickering, including sports at the Markham Pan Am Centre, relaxation at Lynde Shores Conservation Area, and ice skating fun at Cedarena. These attractions offer a delightful mix of adventure, wellness, and entertainment for everyone.

Things to do recommended for groups

In Pickering, groups can enjoy shopping at Scarborough Town Centre, located 6.2km away, and experience outdoor fun at Deer Creek North Golf Course. Don't miss the Herongate Barn Theatre for a delightful evening of entertainment and culture, perfect for families and friends alike.

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

When travelling with a group, family, pets, or seeking extended stays, it’s important to filter according to your specific needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Pickering with a group: Think about the number of bedrooms you require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Pickering with young kids: Traveling with little ones can be quite a task. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Pickering: For many families, a holiday isn’t truly fulfilling without their beloved pet by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Pickering: If you're in search of holiday rentals with offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don't forget to include features such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Pickering

Pickering, Ontario, offers a delightful blend of family-friendly fun and romantic escapes. Explore the charming market town, where you can enjoy local shops and eateries, or take a leisurely stroll along the picturesque River Humber. Don't miss the scenic Potter Hill for a lovely view of the area. With its welcoming atmosphere and great location, Pickering is perfect for creating lasting memories with loved ones.

  • Ajax: Located a mere 1.9km from Pickering, Ajax is a vibrant city that offers a delightful mix of family-friendly activities and urban experiences. Visitors will find an array of shopping options, including a major shopping mall centre. The city also boasts a range of recreational venues, including a popular sports facility stadium and scenic lakes perfect for a leisurely stroll or picnic. Ajax is ideal for those seeking a balance of city life and outdoor enjoyment, making it an excellent choice for families and business travellers alike.
  • Rouge: Just 3.1km from Pickering, Rouge is a picturesque neighbourhood known for its stunning natural landscapes and outdoor adventures. This area is perfect for families looking to enjoy recreational activities, with an amusement park and extensive recreational areas that cater to all ages. The local river and nearby sports facility stadium provide ample opportunities for both relaxation and excitement. Rouge is a haven for nature lovers and those seeking an adventurous getaway, making it a perfect spot for a day out.
  • Port Union: Also situated 3.1km from Pickering, Port Union is a charming neighbourhood that combines urban convenience with outdoor appeal. Families will appreciate the variety of shopping options available at the local shopping centre and mall. The area’s urban parks and sports facility stadium offer excellent venues for leisure and community events. Port Union’s inviting atmosphere makes it a lovely destination for both relaxation and social activities, ideal for those looking to experience the local culture while enjoying outdoor space.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Are you hoping to save on your next getaway? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy platform for planning your trips, allowing you to easily start new ones, continue from where you last stopped, or manage your existing arrangements. You can view your saved or booked properties neatly organised into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Travel to friendly Pickering

The lake and surrounding scenery provide a peaceful ambience to your holiday home in Pickering. Well known for its zoo, hockey games and coffee shops, this welcoming city won't disappoint. Toronto Zoo and Scarborough Town Centre are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Pickering

Do you want to find attractions to visit while you're in the area? Venture out of your holiday home and experience everything that makes Pickering a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Toronto Zoo (5.1 mi / 8.1 km)
  • Deer Creek North Golf Course (7 mi / 11.3 km)
  • Royal Ashburn Golf Club (11.7 mi / 18.8 km)
  • Angus Glen Golf Club (12.5 mi / 20 km)
  • Neb's Funworld (13.2 mi / 21.2 km)
  • Cedar Park Resort (20.3 mi / 32.6 km)

Exploring the natural features in Pickering

Whether you're an adventurous traveller or just want to take in the scenery, Pickering is a great place to get out in nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Rouge National Urban Park (3.9 mi / 6.2 km)
  • Guild Inn Gardens (8.2 mi / 13.3 km)
  • Scarborough Crescent Park (12.1 mi / 19.5 km)
  • Lakeview Park Beach (13.2 mi / 21.2 km)
  • Woodbine Park (16.5 mi / 26.5 km)
  • Woodbine Beach (16.5 mi / 26.6 km)

Transport options to and around Pickering

The nearest airport is in Toronto, ON (YTZ-Billy Bishop Toronto City), located 21 mi (33.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Toronto, ON (YYZ-Pearson Intl.), which is 28.3 mi (45.6 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 holiday rental accommodation in Pickering?
The most desirable types of holiday rentals in Pickering are houses. Prefer something different? Vrbo has numerous options to match the unique needs of our guests, so you'll see holiday 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 holiday rental in Pickering?
Different factors determine how much you'll pay for a holiday rental in Pickering, including the time of year, length of stay and property type. However, all our holiday 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 travelling. 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 holiday rentals in Pickering?
There are, yes. Take your pick of 14 holiday 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 holiday 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 holiday 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 holiday properties have the best amenities for making epic memories with the people that matter most.
Are there holiday rentals in Pickering that welcome kids?
With 14 family-friendly holiday 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 holidaying 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 holiday rentals in Pickering?
Yes, there are four one-bedroom properties in Pickering to pick from. A one-bedroom holiday home is a wonderful option if it's just two of you or if you're travelling 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 holiday rentals in Pickering?
Take your pick of four two-bedroom holiday 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 holiday rentals with WiFi in Pickering?
You can choose from 11 holiday 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 holiday rentals with air conditioning in Pickering?
You can choose from 13 holiday 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.
How old do you have to be to rent a holiday rental in Pickering?
The age limit can differ across properties on Vrbo, so look at the rules of the holiday home in Pickering you want to book. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Pickering for?
It's down to the Pickering property. To see a list of options offering extended stays, simply type your travel dates and guest number into Vrbo. Enjoy having the place to yourself, along with amenities such as air conditioning, a fully-equipped kitchen and a yard where the kids can run around and play. Be on the lookout for long-term stays that offer weekly or monthly discounts.

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