Holiday Rentals in Pickering

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Pickering holiday rentals
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Best Holiday rentals and Airbnb offers in Pickering

Explore Holiday Rentals for Families in Pickering

Getting the holiday rental right makes all the difference for a family trip to Pickering. Find city attractions within easy reach. Start comparing now.

Clean And Spacious 4-bdrm Family Home In Whitby! - Pickering
Pickering
10/10 – 16/10
£143/nighttotal: Â£858 (6 )

Clean And Spacious 4-bdrm Family Home In Whitby!

4 4
apartment , Oshawa
This brand-new four-bedroom house is situated in Whitby, providing swift access to the 412 and 407 motorways within 2 minutes, and is a 30-minute drive from Toronto.
This detached residence offers accommodation for up to ten guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, complimentary WiFi, and private driveway parking for four cars, with attractions such as Lynde Shores Conservation Area and Thermëa Spa Village nearby.
The Continental: Luxury 6b/3.5b + Tesla Charger - Pickering
10 6 reviews
Pickering
27/06 – 24/07
£266/nighttotal: Â£7182 (27 )

The Continental: Luxury 6b/3.5b + Tesla Charger

1 1
apartment , Oshawa
This spacious four-bedroom, three-and-a-half-bathroom flat is situated in Whitby, Ontario, a brief 3.5 kilometre drive from Thermëa Spa and conveniently positioned for access to Petticoat Creek Conservation Park and Lynde Shores Conservation Area.
This family-friendly apartment offers accommodation for up to 12 guests, featuring two living areas, a chef's kitchen, air conditioning, a garden, complimentary parking, and an electric car charger.
Stylish Home Near Luxury Spa & Go Station - Pickering
9.8 301 reviews
Pickering
23/08 – 26/08
£140/nighttotal: Â£420 (3 )

Stylish Home Near Luxury Spa & Go Station

4 1
apartment , Oshawa
This four-bedroom bungalow is situated in a peaceful neighbourhood in Whitby, just a short walk from the Ash Creek Channel Trail and within easy reach of the GO station, Iroquois Park and Port Whitby Marina. The property has received excellent ratings for its cleanliness, location and overall user experience.
The home is ideal for families or groups of up to ten guests, with a spacious living area, a fully equipped kitchen and three bedrooms each accommodating two adults. The apartment also offers a range of amenities and activities, including a private deck and backyard, a fitness centre, a garden, and access to Netflix, Disney+ and Spotify.
Flowers Falls Hideaway: 2-brm 2-wr Condo Retreat - Pickering
9.7 64 reviews
Pickering
27/06 – 04/07
£163/nighttotal: Â£1141 (7 )

Flowers Falls Hideaway: 2-brm 2-wr Condo Retreat

2 2
apartment , Toronto
This one-bedroom flat is located in a trendy district of Toronto, just a short walk from popular attractions and landmarks. It has received excellent ratings for location, cleanliness, and user experience.
The flat has two bathrooms and can accommodate up to four guests. It comes equipped with a modern kitchen, a comfortable living space, and a range of amenities including air conditioning, a garden, a fitness centre, and parking.

Popular Holiday Rentals with Parking in Pickering

On-site parking takes one thing off your list when visiting Pickering. Our holiday rentals have it included.

Beautiful Lakeview Cottage On The Beach - Pickering
9.3 205 reviews
Pickering
03/07 – 07/07
£399/nighttotal: Â£1596 (4 )

Beautiful Lakeview Cottage On The Beach

3 10
cottage , Ajax
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.
452 M² House ∙ 4 Bedrooms ∙ 8 Guests - Pickering
10 1 review
Pickering
30/07 – 05/08
£679/nighttotal: Â£4074 (6 )

452 M² House ∙ 4 Bedrooms ∙ 8 Guests

4 2
house , Toronto
This family-friendly three-bedroom detached house is situated in a quiet, residential area of Ajax, Canada, offering convenient access to major roads and public transport, with the Durham Regional Forest and Ajax Waterfront Park approximately 5 kilometres away.
This spacious accommodation, covering 232 square metres, accommodates up to nine guests with three bedrooms, two bathrooms, a fully equipped kitchen, and garden, and includes amenities such as Wi-Fi, air conditioning, a swimming pool, and parking, while being pet-friendly for up to two animals.
Guest Suite In Ajax/toronto - Pickering
Pickering
01/08 – 30/11
£50/nighttotal: Â£6050 (121 )

Guest Suite In Ajax/toronto

1 2
apartment , Toronto
This newly renovated one-bedroom flat is located in Ajax, offering convenient access to natural attractions such as Rouge National Urban Park and Darlington Provincial Park, and is a drive from the Toronto Zoo and Veterans' Point Gardens.
This modern flat accommodates two guests and features a custom kitchen, dedicated office space, and air conditioning, with check-out at 11:00.
Upscale Pickering Escape | Near Lake & Dining - Pickering
Pickering
03/07 – 07/07
£749/nighttotal: Â£2996 (4 )

Upscale Pickering Escape | Near Lake & Dining

5 10
apartment , Toronto
This five-bedroom, five-bathroom property in Pickering, Ontario, is situated a short 1.8km walk from Lake Ontario and 1.6km from Millennium Square.
The self-catering apartment sleeps ten guests and boasts a fully equipped kitchen, in-unit laundry, parking, air conditioning, Wi-Fi, and a fireplace; nearby attractions include Cineplex Pickering cinemas, Scarborough Golf and Country Club, Toronto Zoo, and Veterans' Point Gardens.

Frequently asked questions about holiday rentals in Pickering

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

    The neighbourhood of Rougemount is a good choice for a vacation rental. It's close to the waterfront and has a variety of restaurants and shops. If you're looking for a more rural setting, the neighbourhood of Pickering Village might be a better fit.
  • What are the best Airbnb and holiday rentals in Pickering?

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

    The Pickering Museum Village is a great place to take the kids, they'll love seeing the old-fashioned buildings and learning about how people used to live. The Toronto Zoo is also a popular choice, and it's only a short drive from Pickering. The waterfront is another great place to spend a day with the family, there's a playground, a splash pad, and plenty of space to run around.
  • What are the most popular Airbnbs 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 or September to October. The weather is still pleasant during these months, but the crowds are smaller and the prices are lower.
  • What are the best holiday rentals with a pool in Pickering?

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

    You can enjoy a picnic at Frenchman's Bay. The Rouge National Urban Park has plenty of free trails to explore. And of course, the Pickering Museum Village is always a great option for a budget-friendly day out.
  • What are the best rentals for families and kids in Pickering?

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

    The Pickering Village Restaurant is a great place to try some local dishes, they have a wide selection of Canadian classics. The Pickering Waterfront Restaurant is also a good choice, they have a beautiful view of the lake and offer a variety of fresh seafood dishes.
  • What are the best rentals or Airbnbs with a jacuzzi in Pickering?

  • What are the best walking or cycling routes in Pickering?

    The Waterfront Trail is a popular walking and cycling route that runs along the shore of Lake Ontario. It's a great way to enjoy the scenery and get some exercise. The Rouge National Urban Park also has a number of trails for walking and cycling, and there's something for everyone, from easy strolls to challenging climbs.
  • 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 for walking and running. The Pickering Waterfront is also pet-friendly, there's a dog park and plenty of space for your furry friend to run around.
  • What are the benefits of choosing a vacation rental in Pickering?

    Vacation rentals offer more space and privacy than a hotel room. They also often have a kitchen and laundry facilities, which can be very convenient for families or groups. And of course, you can often get a better value for your money by choosing a vacation rental.
  • What are the top sports attractions and facilities in Pickering?

    The Pickering Recreation Complex is a great place to find a variety of sports facilities, including an ice rink, a swimming pool, and a fitness centre. The Canadian Tire Motorsport Park is also a popular destination for motorsports fans, they host a variety of races throughout the year.

Destinations nearby

Top Holiday Rentals with a Balcony in Pickering

Choosing a holiday rental in Pickering with a private balcony offers city skyline views that are worth every penny. Compare options and find yours.

Modern 4bedroom Retreat I 2car Parking I Steps From The Ajax Waterfront - Pickering
Pickering
10/10 – 16/10
£249/nighttotal: Â£1494 (6 )

Modern 4bedroom Retreat I 2car Parking I Steps From The Ajax Waterfront

4 4
apartment , Toronto
This modern 4-bedroom house is located in Ajax, just 160 metres from Lake Ontario and the Ajax Waterfront Park, an 8-minute drive from Pickering Casino Resort and a 5-minute drive from Ajax GO Station.
This spacious 9-person residence features air conditioning, a kitchen equipped with a fridge, microwave oven, and dishwasher, a terrace/balcony, a spa, and parking, with a main-floor bedroom and bathroom ideal for families and close proximity to major retailers.
Beautiful New Townhouse In Quiet Neighbourhood - Pickering
9.5 8 reviews
Pickering
10/10 – 16/10
£168/nighttotal: Â£1008 (6 )

Beautiful New Townhouse In Quiet Neighbourhood

4 5
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.
Love And Relax At Dream Catcher Retreat - Pickering
9.8 25 reviews
Pickering
01/10 – 31/10
£90/nighttotal: Â£2700 (30 )

Love And Relax At Dream Catcher Retreat

1 2
apartment , Oshawa
This apartment is situated in Whitby, a town just outside of Oshawa, about 25 kilometres from the Toronto Zoo and 42 kilometres from the Ontario Science Centre. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The flat has one bedroom and one bathroom, spanning 70 square metres and comfortably accommodating up to six guests. It offers a range of amenities, including a fully equipped kitchen, a private garden, and a cosy fireplace, making it perfect for a relaxing getaway.
Central Location 4 Car Parking Semi - Pickering
Pickering
01/08 – 30/11
£111/nighttotal: Â£13431 (121 )

Central Location 4 Car Parking Semi

2 2
apartment , Toronto
This two-bedroom house is conveniently located in Scarborough, just a short distance from Centennial College and Scarborough Town Centre. The surrounding area is peaceful and quiet, offering a welcome escape from the city's hustle and bustle.
The property provides comfortable accommodation for families or groups of friends. Guests can enjoy a private garden, a tennis court, and free Wi-Fi, as well as a fully equipped kitchen and parking.

Best Pickering holiday rentals with air conditioning

Modern Townhome | Boardwalk · Spa · Zoo | Parking - Pickering
10 1 review
Pickering
14/08 – 29/08
£117/nighttotal: Â£1755 (15 )

Modern Townhome | Boardwalk · Spa · Zoo | Parking

1 2
apartment , Toronto
This modern townhome in Pickering offers a 45-minute GO Train commute to downtown Toronto, with restaurants and grocery stores within a 500-meter walk.
This newly built accommodation sleeps four guests and features two bedrooms, two bathrooms, abundant natural light, and two private balconies.
The Reach - Pickering
9.3 11 reviews
Pickering
01/10 – 31/10
£61/nighttotal: Â£1830 (30 )

The Reach

1 2
apartment , Toronto
This Toronto apartment, sleeping up to three guests, is situated in an unspecified district; further location details are unavailable to specify proximity to landmarks such as the CN Tower or the Royal Ontario Museum.
The two-bedroom, two-bathroom property includes a kitchen equipped with a freezer and dishwasher, air conditioning, and parking; additional amenities or the property's size remain undisclosed.
Maple Nest Pickering For Your Stay - Pickering
9.5 4 reviews
Pickering
10/10 – 16/10
£135/nighttotal: Â£810 (6 )

Maple Nest Pickering For Your Stay

4 5
apartment , Toronto
This four-bedroom upper-level residence is located on Westcreek Drive in Pickering, a peaceful, family-friendly district offering straightforward access to Highways 401 and 407, and situated a mere few minutes from local parks, shops, and schools.
This spacious dwelling accommodates up to eight guests, featuring a dedicated workspace, high-speed WiFi, air conditioning, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, with a separate entrance for the basement Airbnb unit ensuring guest privacy.
Entire Home - Spacious 4 Br Detached With Office - Pickering
9.9 52 reviews
Pickering
25/06 – 16/10
£237/nighttotal: Â£26781 (113 )

Entire Home - Spacious 4 Br Detached With Office

4 2
apartment , Toronto
This modern four-bedroom home is situated in Ajax, a town approximately 30 kilometres east of Toronto, within easy reach of the Ajax/Pickering Casino and other amenities. This fully furnished apartment sleeps up to 10 guests and includes amenities such as high-speed internet, Netflix, laundry facilities, and ample parking for up to six cars.
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