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Pickering holiday lettings

We found 627 holiday rentals — enter your dates for availability

Discover a selection of 64 homes, 20 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:10 Jul - 17 Jul

Image gallery for Tree House getaway with swimming, 18km of Hiking and MTN Biking Trails.

Picnic table
10 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)

Tree House getaway with swimming, 18km of Hiking and MTN Biking Trails.

Scugog

8% off
Price is £1,937
for 7 nights, 1 chalet
£277 per night
includes taxes & fees
Tree House getaway with swimming, 18km of Hiking and MTN Biking Trails.

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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. 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)
  • Lynde Shores Conservation Area (9.1 mi / 14.7 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)
  • Toronto Botanical Garden (15.3 mi / 24.6 km)
  • Woodbine Park (16.5 mi / 26.5 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 best area to stay in Pickering when booking a holiday rental?
When considering a holiday rental in Pickering, Ontario, a popular area to stay is near the waterfront. This picturesque neighbourhood offers stunning views of Lake Ontario and easy access to the beautiful waterfront parks. A highlight of this area is the picturesque Frenchman's Bay, where visitors can enjoy a leisurely walk along the boardwalk or participate in various water activities.

Another great option is the proximity to the Pickering Town Centre, which is great for those who enjoy shopping and dining. This lively area is home to numerous shops, restaurants, and entertainment options, making it a convenient choice for visitors seeking a vibrant setting.

In terms of holiday rentals, the waterfront and the town centre both offer a variety of properties to choose from, suiting different preferences and budgets. Whether you're looking for a cosy apartment or a spacious family home, you're likely to find something that suits your needs in these appealing neighbourhoods.
How much does it cost to rent a holiday home in Pickering?
Prices for holiday rentals in Pickering vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Pickering to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Pickering holiday house rentals?
You can find great discounts on house rentals in Pickering on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Pickering?
For renting a beach house in Pickering, the areas along Lake Ontario offer some lovely options. The waterfront neighbourhoods, particularly around Frenchman's Bay, provide access to beautiful sandy beaches and scenic walking trails. Many of the properties in this area come with amenities such as spacious decks with lake views, outdoor dining areas, and barbecues, making them ideal for enjoying the summer weather and waterfront activities.

Further along the shore, the Beachfront Park area features family-friendly beaches and picnic spots, with holiday rentals that often include features like fully equipped kitchens, laundry facilities, and sometimes even private access to the beach. This area is superb for families or groups looking for a relaxing getaway while still having access to local conveniences, such as shops and restaurants.

Additionally, the proximity to parks like the nearby Rouge National Urban Park adds opportunities for hiking and nature walks, making beach house rentals in Pickering an attractive choice for those seeking both relaxation and outdoor adventure.
Are there any houseboat rentals in Pickering?
In Pickering, there are several houseboat rentals available, offering a unique way to experience the scenic waterfront. These houseboats typically feature amenities such as comfortable sleeping quarters, fully equipped kitchens, and outdoor decks for enjoying the beautiful views of Lake Ontario. Many rentals are located near the waterfront parks and recreational areas, providing easy access to activities like boating and fishing.
What is the most popular type of holiday rental accomodation in Pickering?
In Pickering, holiday houses are the most popular type of holiday rental, with around 220 available throughout the area. These homes are often situated in family-friendly neighbourhoods, offering ample space and amenities for larger groups or families. Most holiday houses come with fully equipped kitchens, multiple bedrooms, and outdoor spaces such as gardens or patios, superb for enjoying the pleasant Ontario weather.

Additionally, there are about 56 apartments and 16 condos, which provide more compact accommodations for couples or solo travellers. These units typically feature essential amenities like kitchen facilities and comfortable living areas.
Are there any family house rentals in Pickering?
In Pickering, Ontario, there are numerous family-friendly house rentals available, with around 24 options throughout the area. Visitors can find spacious homes in neighbourhoods like West Shore and Dunbarton, which are ideal for families seeking comfort and convenience. Many of these properties come equipped with full kitchens, allowing for easy meal preparation, and offer ample living spaces where everyone can gather after a day of exploring.

Additionally, families can enjoy outdoor amenities such as private gardens or backyards where children can play safely. The proximity to local parks, such as the scenic Frenchman's Bay and the expansive Rouge National Urban Park, provides excellent opportunities for outdoor activities, including hiking and picnicking.
Can I rent a holiday home with a pool or hot tub in Pickering?
In Pickering, Ontario, there are several holiday homes available for rent that feature pools and hot tubs, providing a refreshing retreat for travellers. The city offers a variety of neighbourhoods where these properties can be found, including areas close to Lake Ontario, which not only enhance the scenic views but also provide access to waterfront activities.

Rentals in Pickering typically come equipped with amenities such as private pools, inviting hot tubs, spacious outdoor areas superb for relaxation, and fully furnished kitchens, making them ideal for families or groups. Some properties may also offer additional features like barbecue facilities and landscaped gardens, enhancing the outdoor experience.
Can I find long-stay holiday rentals in Pickering?
A long-stay holiday rental in Pickering is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Pickering?
In Pickering, Ontario, there are several pet-friendly house rentals available, offering a variety of amenities for a comfortable stay. These homes typically feature spacious layouts, modern kitchens, and outdoor spaces like backyards or patios, making them ideal for families or groups travelling with pets.

The neighbourhoods in Pickering provide access to local parks where pets can enjoy walks and playtime. For example, the nearby Frenchman's Bay offers scenic walking trails along the waterfront, and the expansive Greenwood Park is great for outdoor activities with your furry friends. Additionally, the proximity to the Rouge National Urban Park gives pet owners the opportunity to explore nature trails and engage in hiking, ensuring an enjoyable experience for both pets and their owners.
Are there any remote work holiday rentals in Pickering?
In Pickering, Ontario, there are numerous holiday rentals suitable for remote work, with approximately 224 options available. Many of these properties offer essential amenities for working from home, including free Wi-Fi, dedicated desk spaces, and comfortable living areas that facilitate productivity. You'll find a range of accommodations, from modern apartments to spacious homes, often equipped with kitchen facilities for convenient meal preparation.

The city is conveniently located near points of interest such as the scenic Lake Ontario waterfront, where you can enjoy parks and trails during your breaks. Additionally, the nearby Rouge National Urban Park offers opportunities for outdoor activities and relaxation after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pickering holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Pickering with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Pickering?
In Pickering, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and onsite parking for convenience. Many rentals also feature coffee and tea makers, providing a warm beverage option upon arrival. For those needing to work or stay connected, rentals typically offer desks and desk chairs, creating a comfortable workspace.
When is the best time to visit Pickering for a holiday rental?
The best time to book a holiday rental in Pickering is during the summer months, particularly in July. This peak season, spanning from June to August, invites visitors to enjoy the warm weather and participate in various outdoor activities. With temperatures typically ranging from 20 to 30 degrees Celsius, it's an ideal time for leisurely strolls in the parks or exploration of the scenic waterfront along Lake Ontario.

July is particularly popular, bustling with families and friends taking advantage of the vibrant setting and community events. You can explore local attractions like the Rouge National Urban Park, where hiking trails and beautiful landscapes offer an adventurous escape right at your doorstep.

For those looking for a more budget-friendly option, consider visiting Pickering in January. While this month is quieter, it presents a unique opportunity to experience the beauty of winter. The snowy landscapes can be stunning, and you might enjoy activities such as ice skating or cozying up at local cafés.
How early should I book a Pickering holiday rental?
Book your Pickering holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Pickering?
In Pickering, visitors can explore a variety of attractions that showcase both natural beauty and cultural experiences. The Rouge National Urban Park, located nearby, offers extensive hiking and biking trails amidst stunning landscapes and is a great spot for wildlife observation. For those interested in history, the Pickering Museum Village presents a glimpse into the region's past with its collection of historic buildings and interactive exhibits.

The waterfront area along Lake Ontario, particularly at Frenchman's Bay, is great for leisurely strolls and enjoying the scenic views of the lake. Many holiday rentals in this area provide easy access to the beach and recreational activities such as kayaking and paddleboarding. Additionally, the nearby Durham Live entertainment complex is an emerging destination that promises a range of dining and entertainment options.
Can I change or cancel my Pickering home rental booking on Vrbo?
To find Pickering holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Pickering holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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