Pickering holiday rentals

We found 674 holiday rentals — enter your dates for availability
Discover a selection of 67 homes, 25 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:18 Dec - 25 Dec

Interior
Exterior
Picnic table
Interior
Exceptional
(10 reviews)

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

Scugog

8% off
AU$3,491
for 7 nights, 1 chalet
AU$499 per night
includes taxes & fees
Tree House getaway with swimming, 18km of Hiking and MTN Biking Trails.
Living area
Interior
Backyard with gazebo
Interior
Wonderful
(19 reviews)

Newly renovated luxury Home with deck, surrounded by trees on a 5 acres land

Whitchurch-Stouffville

7% off
AU$4,034
for 7 nights, 1 villa
AU$576 per night
includes taxes & fees
Newly renovated luxury Home with deck, surrounded by trees on a 5 acres land
Property grounds
Living area
Private kitchen
Property grounds
Excellent
(6 reviews)

Serene 5 bedrm entire house on acres land & ponds

Whitchurch-Stouffville

8% off
AU$5,865
for 7 nights, 1 home
AU$838 per night
includes taxes & fees
Serene 5 bedrm entire house on acres land & ponds
Room
Interior
Private kitchen
Interior
Excellent
(20 reviews)

Oshawa Connect: Prime Location, Modern Space

Oshawa

8% off
AU$1,352
for 7 nights, 1 home
AU$193 per night
includes taxes & fees
Oshawa Connect: Prime Location, Modern Space
Living area
Private kitchen
Interior
Living area
Exceptional
(9 reviews)

Charming 2-bedroom house with AC, WiFi in Pleasant Ajax

Ajax

7% off
AU$1,129
for 7 nights, 1 home
AU$161 per night
includes taxes & fees
Charming 2-bedroom house with AC, WiFi in Pleasant Ajax
Private kitchen
Pool
Interior
Property grounds
Exceptional
(7 reviews)

Cozy 2 bedroom basement with pool, jacuzzi, gym & sauna. Come see the chickens

Whitchurch-Stouffville

12% off
AU$2,817
for 7 nights, 1 apartment
AU$402 per night
includes taxes & fees
Cozy 2 bedroom basement with pool, jacuzzi, gym & sauna. Come see the chickens
Property grounds
Private kitchen
Living area
Room
Very good
(5 reviews)

Brand new 2 bedroom basement apartment

Ajax

8% off
AU$1,067
for 7 nights, 1 apartment
AU$152 per night
includes taxes & fees
Brand new 2 bedroom basement apartment
Front view of the House
Stairs to the basement
Bedroom
Kitchen
Exceptional
(21 reviews)

Family Friendly | HOT TUB | Near Toronto & UOIT

Oshawa

7% off
AU$1,161
for 7 nights, 1 apartment
AU$166 per night
includes taxes & fees
Family Friendly | HOT TUB | Near Toronto & UOIT

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Joyride 150 Indoor Bike Park (9.7 mi / 15.6 km)
  • Royal Ashburn Golf Club (11.7 mi / 18.8 km)
  • Angus Glen Golf Club (12.5 mi / 20 km)
  • Willow Springs Winery (13.7 mi / 22 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)
  • Oshawa Valley Botanical Gardens (11.5 mi / 18.5 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)

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.
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.
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 Stayz.
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.
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.
Are all fees included in the Pickering holiday homes prices shown on Stayz?
Stayz 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.
Are there any Pickering holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Pickering holiday homes?
You can find great discounts on holiday homes in Pickering on Stayz, 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.
Can I change or cancel my Pickering holiday home booking on Stayz?
To find Pickering holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pickering?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Pickering holiday home?
Book your Pickering holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pickering?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pickering to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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