Holiday Rentals in Pickering

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Pickering holiday rentals
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1702 Holiday rentals and Airbnb in Pickering

Best family friendly Pickering holiday rentals

Among the 1702 accommodations in Pickering, here are the 4 best family friendly rentals

40 Min To Dt Toronto | 2 Living Spaces | 2 Kitchen - Pickering
10 5 reviews

40 Min To Dt Toronto | 2 Living Spaces | 2 Kitchen

apartment, Oshawa
This modern house, situated in Pickering, Ontario, offers convenient access to the Toronto Zoo (approx. 21km) and Pickering Town Centre (approx. 19km), being less than 40 minutes from Toronto city centre.
Sleeping up to 10 guests, this four-bedroom, three-and-a-half bathroom property features two separate living areas, each with a kitchen, plus a garden, Wi-Fi, Smart TVs, and parking for four cars, making it ideal for families or large groups visiting Oshawa.
Stunning & Bright - My Home Is Close To The Highway & Thermea Spa - Pickering
8.0 7 reviews

Stunning & Bright - My Home Is Close To The Highway & Thermea Spa

apartment, Oshawa
This spacious Whitby holiday home, situated approximately 9.6km from Oshawa's Oshawa Valley Botanical Gardens and Neb's Funworld, and 9.6km from Deer Creek Golf Course, offers convenient access to local attractions.
The 325 square metre property boasts four bedrooms, four bathrooms, sleeps six guests, and includes a fully equipped kitchen, Jacuzzi, fitness centre, and private garden, alongside nearby options for golf and family entertainment.
Wildflower By The Bay - Pickering
10 90 reviews

Wildflower By The Bay

house, Toronto
This Pickering guest suite, a short walk from Lake Ontario and the Waterfront Trail, offers easy access to Toronto's city centre via Pickering GO station (a 40-minute train journey).
The self-contained apartment features a queen bed, a sofa bed, a kitchenette with microwave and fridge, accommodating up to three guests and is located close to a park and playground.
Modern Nest - 5 Beds, 2.5 Baths, 3 Park, Backyard - Pickering
9.8 74 reviews

Modern Nest - 5 Beds, 2.5 Baths, 3 Park, Backyard

apartment, Oshawa
This four-bedroom, two-bathroom family-friendly apartment in Pickering, Ontario, is situated approximately 23km from the Toronto Zoo and 19km from Pickering Town Centre.
The self-catering property sleeps ten guests, offers free parking for three cars, and includes a fully equipped kitchen, dedicated workspace, and family amenities such as a cot and high chair.

Best Pickering holiday rentals with parking

Guest Suite In Ajax/toronto - Pickering
9.9 15 reviews

Guest Suite In Ajax/toronto

apartment, Toronto
This one-bedroom flat in North Ajax, Ontario, offers convenient access to the 401 Highway (a 6-kilometre drive) and is situated within a manageable drive of Toronto and its international airport.
This well-appointed accommodation for two guests boasts a private garden, air conditioning, and a fully equipped kitchen, with the added convenience of on-site parking and immediate proximity to local amenities including restaurants and shops, alongside family-friendly attractions like a public playground directly opposite.
"Suite Escape" In Pickering - Pickering
9.9 47 reviews

"Suite Escape" In Pickering

apartment, Toronto
This Pickering apartment, situated near the intersection of Highways 401 and 407, offers easy access to Lake Ontario's waterfront, the Pickering Casino Resort, and the surrounding shopping and entertainment options.
The newly renovated self-catering flat features a queen-size bed, office space, living room, kitchenette, and washer/dryer; accommodating two guests and providing complete privacy with its private entrance, soundproofing, and tile flooring.
Cozy Studio: Private, Free Parking & Great Deals! - Pickering
8.4 11 reviews

Cozy Studio: Private, Free Parking & Great Deals!

studio, Toronto
This Pickering flat is situated 3.7km from Rouge National Urban Park and 3.9km from Lake Ontario, with the Toronto Zoo and Herongate Barn Theatre within a 9.7km radius, offering easy access to Toronto's attractions while enjoying a quieter suburban setting.
The one-bedroom, one-bathroom apartment sleeps two guests and includes convenient on-site parking, a microwave, Smart TV, and hair dryer, alongside a smoke-free environment.
Little Haven Loft - Pickering
9.4 3 reviews

Little Haven Loft

apartment, Oshawa
This flat is situated in Whitby, offering convenient access to Rouge National Urban Park and Darlington Provincial Park, with the Toronto Zoo and Oshawa Valley Botanical Gardens also within reach.
This two-bedroom flat accommodates up to four guests and includes internet and air conditioning, providing a comfortable base for exploring nearby attractions such as Neb's Funworld.

Frequently asked questions about holiday rentals in Pickering

  • What should a first-time visitor not miss in Pickering?

    If you're visiting Pickering for the first time, you should definitely check out the Pickering Museum Village. It's a great way to learn about the history of the area and see how people lived in the 19th century. Also, be sure to visit the Rouge National Urban Park. It's a beautiful place to go for a hike, bike ride, or picnic.
  • What are the best Airbnb and holiday rentals in Pickering?

  • Which neighborhood in Pickering should you consider for a vacation rental?

    The best neighbourhood to find a vacation rental in Pickering would be the one near Frenchman's Bay. It's a lovely area with easy access to the waterfront and the Rouge National Urban Park. You can find a range of rentals from apartments to houses, depending on your budget and needs.
  • What are the most popular Airbnbs in Pickering?

  • What are the top family-friendly attractions in Pickering?

    Pickering has a lot to offer families. The Pickering Museum Village is a great place to visit with kids, and the Rouge National Urban Park is perfect for a day of outdoor fun. The Toronto Zoo is just a short drive away and is always a popular choice for families.
  • What are the best holiday rentals with a pool in Pickering?

  • When is the best time to book a vacation rental in Pickering?

    The best time to book a vacation rental in Pickering would be during the shoulder seasons, from April to June and September to October. You'll find better deals and fewer crowds during these months.
  • What are the best rentals for families and kids in Pickering?

  • What are the best budget-friendly activities in Pickering?

    For budget-friendly activities, there's a lot to do in Pickering. The Rouge National Urban Park is free to enter and offers plenty of hiking and biking trails. You can also explore the Pickering Museum Village, which has free admission on certain days of the week.
  • What are the best rentals or Airbnbs with a jacuzzi in Pickering?

  • What are the best restaurants with local dishes in Pickering?

    For local dishes, you should try the pickerel at The Captain's Boil on Kingston Road. It's a popular spot for fresh seafood and a great place to try some local fare. You can also find some great restaurants in the Pickering Village area.
  • What are the best walking or cycling routes in Pickering?

    The most popular walking and cycling routes in Pickering are located within the Rouge National Urban Park. The park has a variety of trails, ranging from easy to challenging, so there's something for everyone. The Waterfront Trail is another great option for a scenic walk or bike ride.
  • Are there pet-friendly attractions in Pickering?

    Yes, there are a number of pet-friendly attractions in Pickering. The Rouge National Urban Park is a great place to take your dog for a walk, and many of the restaurants and cafes in the Pickering Village area are also pet-friendly.
  • What are the benefits of choosing a vacation rental in Pickering?

    Choosing a vacation rental in Pickering can offer a more spacious and comfortable stay than a hotel. You'll also have access to a kitchen and laundry facilities, which can be convenient for families or longer stays.
  • What are the top sports attractions and facilities in Pickering?

    Pickering is home to several sports facilities, including the Pickering Recreation Complex, which features a swimming pool, fitness centre, and ice rink. The city also has a number of parks and trails that are perfect for outdoor sports activities.

Popular destinations

Best Pickering holiday rentals with a balcony

Stylish Home Near Luxury Spa & Go Station - Pickering
No reviews

Stylish Home Near Luxury Spa & Go Station

apartment, Oshawa
This downtown Whitby flat offers a prime location, placing you within easy reach of the beach, Landmark Cinemas Whitby, and All or Nothing Distillery, with Lake Ontario and Darlington Provincial Park just a short distance away.
This spacious 4-bedroom, 2-bathroom maisonette provides Wi-Fi, air conditioning, a private garden, and a terrace, alongside practical amenities like laundry facilities, making it ideal for families seeking access to outdoor pursuits such as kayaking, cycling, and hiking.
Beautiful New Townhouse In Quiet Neighbourhood - Pickering
9.5 8 reviews

Beautiful New Townhouse In Quiet Neighbourhood

house, Toronto
This four-bedroom townhouse is located in Ajax, a suburb of Toronto, 21 km from the Toronto Zoo and 38 km from the Ontario Science Centre, offering a peaceful escape from the city. The property is conveniently located within easy reach of Toronto's attractions and amenities.
The 46 square metre townhouse comfortably accommodates eight guests and features a living room, fully equipped kitchen, and three bathrooms. Guests can enjoy modern amenities such as air conditioning, free Wi-Fi, a flat-screen TV, laundry facilities, and private parking.
Beautiful New Townhouse In Quiet Neighbourhood - Pickering
9.2 96 reviews

Beautiful New Townhouse In Quiet Neighbourhood

apartment, Toronto
This modern four-bedroom house is situated in Ajax, a suburb of Toronto, just 30km east of the city centre and close to the 401 highway. It has received excellent ratings for location, cleanliness and user experience.
This spacious property comfortably sleeps eight guests and provides full access to all areas. It has a fully equipped kitchen, a garden, parking and air conditioning, as well as being close to the beach, parks and a shopping mall.
Modern Gem| 2026 Fifa - 40 Mins To Bmo Field | Thh - Pickering
No reviews

Modern Gem| 2026 Fifa - 40 Mins To Bmo Field | Thh

house, Toronto
This three-bedroom, three-bathroom Ajax townhouse, situated approximately 30km from Toronto and close to Parkwood Estate and the Markham Museum, offers convenient access to local amenities and attractions.
The 185 square metre property boasts a fully equipped kitchen, a terrace, parking, super-fast Wi-Fi (3.5 Gbps), and accommodates up to 10 guests, making it ideal for families or groups visiting the Toronto area.

Best Pickering holiday rentals with air conditioning

Bravas Maple  5br Home  Uoft + Centennial + Zoo - Pickering
9.2 5 reviews

Bravas Maple 5br Home Uoft + Centennial + Zoo

apartment, Toronto
This spacious upper-level flat is located in a prime Scarborough district of Toronto, a short 5-kilometre drive from the Toronto Zoo and close to scenic nature trails.
This accommodation offers five Queen-sized bedrooms, three and a half bathrooms including a master ensuite with a jacuzzi tub, a fully-equipped chef's kitchen, two living areas, and a large private garden, comfortably hosting up to 16 guests with on-site laundry facilities.
Private Look-out Basement
2bed 1 Bath Full Kitchen - Pickering
9.9 26 reviews

Private Look-out Basement 2bed 1 Bath Full Kitchen

apartment, Toronto
This two-bedroom flat is located in a Toronto district, offering convenient access to local attractions.
This 119-square-meter flat accommodates up to four guests and features a custom kitchen, air conditioning, parking, and a unique '2 steps down lookout' for a distinctive living experience.
Elysium Where Happiness Is Real! - Pickering
9.9 431 reviews

Elysium Where Happiness Is Real!

apartment, Toronto
This basement flat is located in Pickering, a suburb east of Toronto, just a short drive from the Toronto Zoo, Pickering Casino, and Pickering Town Centre. The property has received excellent ratings for its cleanliness, location, and overall experience.
The self-contained flat can accommodate two guests and has a private entrance, ensuring privacy and independence. Guests can enjoy access to a range of amenities including a fully equipped kitchen, a comfortable living area with a TV and high-speed internet, and a private garden.
Luxury Basement Apartment - Pickering
10 1 review

Luxury Basement Apartment

apartment, Toronto
This Toronto basement flat, sleeping seven comfortably in two bedrooms and one bathroom, offers a private entrance and ample storage.
The self-catering property includes a fully equipped kitchen, air conditioning, parking, and excellent guest reviews; further details regarding its precise Toronto neighbourhood and proximity to landmarks are needed.
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