Compare Vacation Rentals & Airbnb in Pickering

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Pickering vacation rentals
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1702 Rentals and Airbnb in Pickering

Best family friendly Pickering vacation rentals

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

Executive Retreat/forest Trails/golfing/skating - Pickering
10 2 reviews

Executive Retreat/forest Trails/golfing/skating

apartment, Scugog
This executive forest retreat is located in Whitby, a rural district adjacent to the Royal Ashburn Golf Club, offering convenient access to Durham Forest's scenic trails and the charming towns of Port Perry and Oshawa, which are within a 20-kilometre radius.
This 93 square metre apartment, suitable for up to four guests, provides a countryside living experience with a terrace/balcony, garden, air conditioning, and a kitchen equipped with a fridge, microwave, and dishwasher, while nearby attractions include Port Perry Fair Ground and Lynde Shores Conservation Area.
Stunning Luxe Design | 4 Br | Whitby | Thermea - Pickering
10 3 reviews

Stunning Luxe Design | 4 Br | Whitby | Thermea

apartment, Oshawa
This exclusive 4-bedroom residence is situated on a quiet cul-de-sac in North Whitby, just 150 metres from the Thermëa Spa Village and directly opposite the 100-hectare Heber Down Conservation Area.
This family-friendly property offers accommodation for up to 8 guests, featuring a fully equipped kitchen with a dining table for 13, air conditioning, a garden, and a fitness centre, with 3 driveway parking spaces available.
Beautiful Lakeview Cottage On The Beach!! - Pickering
9.3 208 reviews

Beautiful Lakeview Cottage On The Beach!!

apartment
This charming cottage is located in south Ajax, Ontario, just 20 kilometres east of Toronto, directly on Paradise Beach. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
This spacious three-bedroom cottage offers over 200 square metres of living space, comfortably accommodating up to 11 guests. The cottage includes a fully equipped kitchen, laundry facilities, a terrace, and a garden, as well as a barbecue grill for enjoying summer evenings.
3-bed 3-bath Cozy Vacation House In Ajax, Greater Toronto Area, On, Canada - Pickering
9.2 19 reviews

3-bed 3-bath Cozy Vacation House In Ajax, Greater Toronto Area, On, Canada

apartment, Toronto
This three-bedroom apartment is situated in Ajax, a quiet town just 11 miles east of Toronto Zoo and 21 miles east of the Ontario Science Centre, offering easy access to Toronto via car or public transport. It has received excellent ratings for location, cleanliness, and overall user experience.
The spacious 163 square metre flat comfortably accommodates six guests with three bathrooms and a fully-equipped kitchen. Guests can enjoy outdoor dining on the patio, relax in the shared lounge area, and benefit from amenities such as free parking, laundry service, and a flat-screen TV with streaming services.

Best Pickering vacation rentals with parking

#1 Best Deal In Scarborough - Pickering
9.8 44 reviews

#1 Best Deal In Scarborough

apartment, Toronto
This spacious Toronto house, conveniently located near downtown Toronto with easy access to Highway 401, provides effortless travel to and from Toronto Pearson International Airport.
The four-bedroom, three-bathroom property sleeps eight guests and boasts a fully equipped kitchen, a garden, a fitness centre, and two parking spaces, alongside a 4K microLED smart TV and high-quality linens.
Newly Renovated 2br Basement Suite, Private Entry - Pickering
9.3 4 reviews

Newly Renovated 2br Basement Suite, Private Entry

apartment, Claremont
This one-bedroom basement flat in Pickering offers a private entrance, situated 35 kilometres from The Distillery District and 39 kilometres from Ryerson University, with convenient complimentary private parking.
This family-friendly apartment spans 56 square metres, accommodating up to seven guests with a fully equipped kitchen including a dishwasher and oven, air conditioning, free Wi-Fi, and an in-unit washing machine, located 11 kilometres from the Toronto Zoo and 34 kilometres from the Ontario Science Centre.
Brand New Private Luxury Suite Open Consept Living - Pickering
9.9 215 reviews

Brand New Private Luxury Suite Open Consept Living

apartment, Toronto
This Ajax, Ontario private suite offers convenient access to Toronto, a 48km drive from the city centre, situated near the 401 highway and Ajax GO station.
The self-contained apartment sleeps four, boasting a fully equipped kitchen with new appliances, a jacuzzi, a 65-inch LG Smart TV with streaming services, and a dedicated workspace.
Spacious, Modern & Cozy Retreat - Pickering
9.8 37 reviews

Spacious, Modern & Cozy Retreat

apartment, Toronto
This Toronto Airbnb, ideally located near major highways and shopping centres, offers easy access to the city's attractions.
Sleeping up to 12 guests, this four-bedroom, three-bathroom house boasts a fully equipped kitchen, private backyard, and excellent guest reviews.

Frequently Asked Questions about vacation rentals in Pickering

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

    For a first-time visit, you should definitely check out the Rouge National Urban Park. It's a beautiful spot with lots of walking trails and wildlife to see. If you're interested in history, head to the Pickering Museum Village to see what life was like in the 19th century.
  • What are the best Airbnb and vacation rentals in Pickering?

    Private Apartment W/separate Entrance, Mercedes Palace and Love And Relax At Dream Catcher Retreat are the most popular Airbnb and vacation rentals in Pickering among travelers.

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

    The neighbourhood of Frenchman's Bay is a popular choice for vacation rentals. It's close to the waterfront and has a good selection of restaurants and shops. If you're looking for something more quiet, the neighbourhood of Rougemount is a good option.
  • What are the most popular Airbnbs in Pickering?

    Among the Airbnbs in Pickering, Private Apartment W/separate Entrance, Mercedes Palace and Love And Relax At Dream Catcher Retreat are the most popular ones.

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

    Pickering has lots to offer families! The Toronto Zoo is just a short drive away and is a great day out for all ages. For a more local experience, head to the Pickering Museum Village for a glimpse into the past. The waterfront is also a great spot for families, with playgrounds and picnic areas.
  • What are the best vacation 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 is during the shoulder seasons, from April to June and September to October. You'll avoid the crowds and get better prices. If you're looking for a summer holiday, book well in advance as rentals tend to get booked up quickly.
  • What are the best rentals for families and kids in Pickering?

  • What events or festivals should visitors check out in and around Pickering?

    Pickering has a few events throughout the year, but the biggest one is the Pickering Village Festival in July. This is a great event for families, with live music, food stalls, and activities for kids. The nearby city of Toronto also has a lot of festivals and events throughout the year.
  • What are the best rentals or Airbnbs with a jacuzzi in Pickering?

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

    There are plenty of free things to do in Pickering. Take a walk or cycle along the waterfront, visit the Pickering Museum Village, or explore the Rouge National Urban Park. You can also find free events at the Pickering Recreation Complex.
  • What are the best restaurants with local dishes in Pickering?

    For a taste of local cuisine, try the Pickering Village Restaurant. They have a great selection of traditional Canadian dishes. If you're looking for something a bit more casual, head to the Pickering Market for a variety of food stalls.
  • What are the best walking or cycling routes in Pickering?

    The Waterfront Trail is a great option for both walking and cycling. It stretches along the Lake Ontario shoreline and offers stunning views. For a shorter walk, try the Rouge National Urban Park trails.
  • Are there pet-friendly attractions in Pickering?

    The Rouge National Urban Park is a great place to bring your dog. There are plenty of trails and open spaces for them to run around. Many restaurants and cafes in the area also welcome dogs.
  • What are the benefits of choosing a vacation rental in Pickering?

    Vacation rentals offer more space and privacy than a hotel room. They can also be a more cost-effective option, especially for families or groups. Many rentals also offer amenities that you won't find in a hotel, such as a kitchen and laundry facilities.
  • What are the top sports attractions and facilities in Pickering?

    Pickering has a variety of sports facilities, including the Pickering Recreation Complex, which has a swimming pool, ice rink, and fitness centre. The city is also home to the Pickering Panthers, a junior hockey team that plays in the Ontario Junior Hockey League.

Popular destinations

Best Pickering vacation rentals with a balcony

Stunning & Bright - My Home Is Close To The Highway & Thermea Spa - Pickering
8.4 5 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.
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.
Willow Nest - 5 Beds, 2.5 Baths, 3 Park, Backyard, Thermea Spa - Pickering
10 1 review

Willow Nest - 5 Beds, 2.5 Baths, 3 Park, Backyard, Thermea Spa

apartment, Oshawa
This Whitby residence, a 3-bedroom, 2-bathroom flat, is situated 9 minutes by car from Lake Ontario and 18 minutes from the Toronto Zoo.
This pet-friendly holiday home accommodates up to 8 guests and features air conditioning, complimentary Wi-Fi, a full kitchen with an oven and hob, and an in-unit washer and dryer, with outdoor relaxation provided by a garden and sunroom.
Family Home Near Toronto, Game Room, Backyard, Parking, Self-checkin - Pickering
9.4 18 reviews

Family Home Near Toronto, Game Room, Backyard, Parking, Self-checkin

house, Toronto
This three-bedroom house is situated in Pickering, a suburb of Toronto, located 27 kilometres from the Ontario Science Centre and 37 kilometres from the Royal Ontario Museum, offering a peaceful escape from the city's hustle and bustle. The property has received excellent ratings for cleanliness, location and overall experience.
This spacious home, covering 19 square metres, comfortably accommodates up to seven guests. The house features a fully equipped kitchen, a private balcony with garden views, a water park, complimentary Wi-Fi, private parking, and is conveniently located near cycling and hiking trails.

Best Pickering vacation rentals with air conditioning

Modern 2bed/1bath + Parking - Pickering
9.2 69 reviews

Modern 2bed/1bath + Parking

apartment, Toronto
This two-bedroom flat is located in Ajax, Ontario, approximately 40 kilometres east of downtown Toronto, offering convenient access to local schools, parks, plazas, and grocery stores.
This well-appointed accommodation features a bright, open-concept living and kitchen area, a private entrance, air conditioning, in-suite laundry, a sofa bed for up to five guests, and dedicated driveway parking.
Little Haven - Pickering
9.4 40 reviews

Little Haven

apartment, Toronto
This peaceful apartment is situated in a quiet neighbourhood, just a short drive from the iconic CN Tower, offering a tranquil escape from the city's hustle and bustle. The apartment enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The two-bedroom flat comfortably accommodates up to four guests and features a well-equipped kitchen with a fridge and microwave oven, air conditioning, parking, and internet access. Enjoy the convenience of a tranquil haven with easy access to Toronto's attractions.
Spacious Basement Apartment In Rouge Hill Near Highway 401 - Pickering
No reviews

Spacious Basement Apartment In Rouge Hill Near Highway 401

apartment, Toronto
This Scarborough flat offers convenient access to the Toronto Zoo, Pickering Casino, and the Rouge Hill GO Station, situated near Highway 401.
This two-bedroom property accommodates up to four guests, featuring a well-equipped kitchen, a dedicated workspace, Wi-Fi, a television, and on-site laundry facilities.
Bright Walkout Suite - Private Entrance - Pickering
8.8 12 reviews

Bright Walkout Suite - Private Entrance

apartment, Toronto
This one-bedroom flat in Ajax offers excellent access to the 401 highway and the Ajax GO Station, placing downtown Toronto attractions within a 30-kilometre drive.
This modern suite accommodates two guests and features a kitchenette, air conditioning, WiFi, dedicated parking, and complimentary toiletries for a comfortable stay.
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