Holiday Rentals in Pickering

1167 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Pickering holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

1167 Holiday rentals and Airbnb in Pickering

Best family friendly Pickering holiday rentals

Among the 1167 accommodations in Pickering, here are the 4 best family friendly rentals

Cozy Suite-close To Pickering Casino Resort, Dog Parks, And Waterfront Trail - Pickering
10 7 reviews
Pickering
30/07 – 05/08
110 â‚¬/nighttotal: 660 â‚¬ (6 )

Cozy Suite-close To Pickering Casino Resort, Dog Parks, And Waterfront Trail

1 2
apartment , Toronto
This self-contained basement flat in Ajax, Ontario, offers easy access to Deer Creek Golf Course and Lake Ontario, approximately 30-40km from Toronto attractions including the Toronto Zoo and Veterans' Point Gardens.
The one-bedroom, one-bathroom apartment sleeps three guests and features a fully equipped kitchenette, private entrance, air conditioning, parking, and internet access; nearby recreational activities include golfing and exploring Rouge National Urban Park.
The Lake View Stay - Pickering
9.6 43 reviews
Pickering
22/08 – 02/09
130 â‚¬/nighttotal: 1430 â‚¬ (11 )

The Lake View Stay

1 4
apartment , Toronto
This two-bedroom apartment is located in Ajax, a town just 15 kilometres east of Toronto, offering a peaceful setting with easy access to nature trails, parks, a lake and a golf course.
The apartment has a modern open-plan design, accommodating up to five guests, and includes a fully equipped kitchen, a garden with a barbecue area, and a basement for extra storage or relaxation. Guests can enjoy free Wi-Fi, a TV, air conditioning and laundry facilities for stays longer than five days.
Toronto [45 Mins] Sleep 8| Free Parking | Backyard - Pickering
10 156 reviews
Pickering
10/10 – 16/10
271 â‚¬/nighttotal: 1626 â‚¬ (6 )

Toronto [45 Mins] Sleep 8| Free Parking | Backyard

1 5
apartment , Claremont
This four-bedroom apartment is located in a suburban area near Claremont, Ontario, approximately 72 kilometres from central Toronto, and within a 24-kilometre drive of attractions such as the Toronto Zoo, Thermea Spa, and Pickering Casino. The spacious self-catering property is ideal for families or groups of up to eight, with dedicated workspaces, a modern kitchen equipped with appliances such as a dishwasher, microwave, and oven/air fryer, and a 65-inch OLED smart TV for entertainment.
Cozy Private Detached Entire Coach House - Pickering
Pickering
26/08 – 25/11
81 â‚¬/nighttotal: 7371 â‚¬ (91 )

Cozy Private Detached Entire Coach House

1 2
apartment , Toronto
This pet-friendly flat in Markham, a district of Toronto, is situated 640 metres by car from Markham Museum and 966 metres from Markham Village.
This one-bedroom, one-bathroom flat accommodates up to three guests and includes air conditioning, Wi-Fi, a fully equipped kitchen with an oven and stovetop, and on-site parking, with proximity to the Toronto Zoo and Cedarena.

Best Pickering holiday rentals with parking

Luxury Stay W/ Chefs Kitchen - Pickering
Pickering
30/07 – 05/08
405 â‚¬/nighttotal: 2430 â‚¬ (6 )

Luxury Stay W/ Chefs Kitchen

3 2
apartment , Toronto
This Pickering holiday home is situated 0.8km from Lake Ontario, 4.8km from Rouge National Urban Park, and 9.6km from Pickering Casino Resort, offering easy access to Toronto-area attractions.
The three-bedroom, two-bathroom property sleeps six guests and boasts a fully equipped kitchen with appliances including a fridge, microwave, and dishwasher, plus free Wi-Fi, on-site parking, and air conditioning.
Beautiful One Bedroom Basement Apartment - Pickering
Pickering
20/10 – 27/04
81 â‚¬/nighttotal: 15309 â‚¬ (189 )

Beautiful One Bedroom Basement Apartment

1 2
apartment , Toronto
This Scarborough flat is conveniently located 1.8km from Morningside Park, within 4.8km of Guild Inn Gardens and Lake Ontario, and 4.2km from Centennial College.
The one-bedroom, one-bathroom apartment sleeps three, offering free parking, Wi-Fi, a fully equipped kitchen with appliances including a microwave and oven, plus a dryer, Smart TV, and coffee/tea maker.
Spacious 3 Br Suite With Parking, Backyard & Desk - Pickering
10 1 review
Pickering
20/06 – 27/06
144 â‚¬/nighttotal: 1008 â‚¬ (7 )

Spacious 3 Br Suite With Parking, Backyard & Desk

1 2
apartment , Toronto
This Toronto flat is located 25.75 kilometres from Billy Bishop Toronto City Airport, offering a location removed from the immediate downtown core.
This one-bedroom flat, suitable for up to 11 guests, features a fully equipped kitchen with an oven and microwave, air conditioning, complimentary high-speed WiFi, and 6 square metres of floor area, with private check-in and check-out available.
Cozy Entire Apartment - Quiet & Privacy - Pickering
8.0 2 reviews
Pickering
14/08 – 29/08
172 â‚¬/nighttotal: 2580 â‚¬ (15 )

Cozy Entire Apartment - Quiet & Privacy

2 2
apartment , Toronto
This Pickering apartment, situated approximately 0.8km from Lake Ontario, offers easy access to Rouge National Urban Park and Millennium Square, providing a peaceful suburban escape near Toronto's attractions.
This two-bedroom, one-bathroom flat sleeps four guests and includes free Wi-Fi, on-site parking, and air conditioning; nearby attractions include Pickering Casino Resort (within 9.6km).

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.

Destinations nearby

Best Pickering holiday rentals with a balcony

Beautiful Lakeview Cottage On The Beach - Pickering
9.3 205 reviews
Pickering
10/10 – 16/10
329 â‚¬/nighttotal: 1974 â‚¬ (6 )

Beautiful Lakeview Cottage On The Beach

3 4
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.
Love And Relax At Dream Catcher Retreat - Pickering
9.8 25 reviews
Pickering
22/08 – 02/09
133 â‚¬/nighttotal: 1463 â‚¬ (11 )

Love And Relax At Dream Catcher Retreat

1 4
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.
Willow Nest - 5 Beds, 2.5 Baths, 3 Park, Backyard, Thermea Spa - Pickering
10 1 review
Pickering
14/08 – 29/08
308 â‚¬/nighttotal: 4620 â‚¬ (15 )

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

3 2
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.
Modern 4bedroom Retreat I 2car Parking I Steps From The Ajax Waterfront - Pickering
Pickering
10/10 – 16/10
151 â‚¬/nighttotal: 906 â‚¬ (6 )

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

4 4
house , Toronto
This four-bedroom detached house is situated in Ajax, 19 kilometres from the Toronto Zoo and a short walk from the Ajax Waterfront, with Paradise Beach 2.4 kilometres away.
This property offers 167 square metres of living space, accommodating up to 15 guests with four bedrooms and four bathrooms, and includes a fully equipped kitchen, WiFi, air conditioning, and a balcony.

Best Pickering holiday rentals with air conditioning

Sun Shine - Pickering
Pickering
23/06 – 23/07
111 â‚¬/nighttotal: 3330 â‚¬ (30 )

Sun Shine

1 4
apartment , Toronto
This Toronto flat is located in a family-friendly district, providing easy access to key city landmarks.
This property accommodates up to four guests and offers amenities including a kitchen, air conditioning, and internet, making it suitable for families exploring Toronto's attractions.
Fb04-cozy Holiday Home - Pickering
Pickering
20/10 – 27/04
31 â‚¬/nighttotal: 5859 â‚¬ (189 )

Fb04-cozy Holiday Home

1 2
apartment , Toronto
This one-bedroom flat is situated in Scarborough, Toronto, a convenient base for visitors to the University of Toronto Scarborough Campus and Centennial College, with TTC bus stops a mere 200 metres away for easy access to the city.
This basement apartment offers WiFi, air conditioning, and a shared kitchen and bathroom, accommodating up to two guests with a queen-size bed, and is located 3 kilometres from Lake Ontario and the Scarborough Town Centre.
Guildwood Stays - 3 Bedroom Beautiful Home - Pickering
Pickering
23/06 – 23/07
102 â‚¬/nighttotal: 3060 â‚¬ (30 )

Guildwood Stays - 3 Bedroom Beautiful Home

1 4
apartment , Toronto
This three-bedroom house in Guildwood, Scarborough, is a short walk from Guildwood GO station and local buses to Kennedy Subway Station, offering easy access to Toronto's public transport network.
The property features a full kitchen with modern appliances, three queen-sized bedrooms sleeping six guests, a full bathroom with a bathtub, and convenient on-street parking.
Modern Suite | Private Entry | 401/go + Parking - Pickering
9.5 4 reviews
Pickering
10/10 – 16/10
168 â‚¬/nighttotal: 1008 â‚¬ (6 )

Modern Suite | Private Entry | 401/go + Parking

1 4
apartment , Toronto
This executive suite is located in an upscale Pickering neighbourhood, offering convenient access within minutes to Highway 401, the GO Station, shopping, dining, and the casino.
This spacious 102 square meter legal basement apartment, featuring 10-foot ceilings and an open layout, comfortably accommodates up to six guests with two double beds and a sofa bed, and includes a fully equipped kitchen, in-suite laundry, a Smart TV, and private parking for two vehicles.
©2026 cozycozy.com