Vacation Rentals in Pickering

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Pickering holiday rentals
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1702 Holiday rentals and Airbnb in Pickering

Outstanding Family Holiday Rentals in Pickering, Canada

Book a spacious home base equipped with a full kitchen and open living areas at family holiday rentals in Pickering, Canada.

Flowers Falls Hideaway | Modern 2br Condo Escape - Pickering
9.7 70 reviews

Flowers Falls Hideaway | Modern 2br Condo Escape

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.
Clean And Modern Guest Suite In Whitby - Pickering
9.8 31 reviews

Clean And Modern Guest Suite In Whitby

apartment, Oshawa
This two-bedroom apartment is situated in Whitby, just a short drive from the Whitby History Museum & Children's Centre, Lake Ontario, and the Ontario Regiment Museum. It's rated excellent by previous guests, making it a popular choice for travellers seeking a comfortable stay.
The flat comfortably accommodates four guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher. Guests can enjoy modern amenities like free Wi-Fi, a Smart TV, and a coffee maker, as well as in-unit laundry facilities and parking.
A Beautiful Walkout Basement - Pickering
9.6 10 reviews

A Beautiful Walkout Basement

apartment, Toronto
This spacious 3-bedroom, 1-bathroom flat is situated in Pickering, a district east of Toronto, offering convenient access to local points of interest such as the Markham Museum and Markham Village, and within reasonable travel distance of the Toronto Zoo and Cedarena.
This extensive 185-square-metre walkout basement dwelling comfortably accommodates up to six guests and features essential amenities including a fridge, microwave, dishwasher, and air conditioning, with parking and a garden also available for your convenience.
Family Home Near Toronto, Game Room, Backyard, Parking, Self-checkin - Pickering
9.4 14 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 holiday rentals with parking

Apartment In Pickering - Pickering
9.8 8 reviews

Apartment In Pickering

apartment, Toronto
This self-contained flat is situated in Pickering, a 5-minute drive from Pickering Town Centre and the M401, offering park views from its lower-level position, ideal for those seeking a convenient base for exploring the Greater Toronto Area.
The accommodation features one bedroom and one bathroom, accommodating up to two guests, and includes a private patio, backyard access with a barbecue, in-unit laundry, and air conditioning, with Centennial Park nearby for outdoor recreation.
2 Plush Queen Beds + 1 Sofa-bed - Sleeps 6 - Apt - Pickering
9.9 204 reviews

2 Plush Queen Beds + 1 Sofa-bed - Sleeps 6 - Apt

apartment, Toronto
This three-bedroom flat is situated in a convenient location near the Highway 401, just a 5-minute drive from the GO Train station and within easy reach of the Toronto Zoo.
The self-contained apartment features a fully equipped kitchen, an iMac and printer for remote working, and a private entrance with self-check-in, perfect for families or groups of up to six people.
Private 2bedroom Unit, Free Parking, Free From Smoke & Pet, Self-check In - Pickering
9.1 61 reviews

Private 2bedroom Unit, Free Parking, Free From Smoke & Pet, Self-check In

apartment, Toronto
This Pickering apartment, situated 16 kilometres from the Toronto Zoo and 42 kilometres from downtown Toronto attractions such as the Distillery District, offers a peaceful suburban retreat.
The 65 square metre self-catering flat features two bedrooms, one bathroom, sleeps eleven guests, and includes free Wi-Fi, private parking, and a garden.
Lake Breeze 1 Bedroom Basement Apartment - Pickering
No reviews

Lake Breeze 1 Bedroom Basement Apartment

house, Toronto
This tranquil and stylish apartment is located in a Toronto district, offering a peaceful retreat within easy reach of key attractions such as the CN Tower, located approximately 3 kilometres away.
This one-bedroom, one-bathroom flat accommodates up to two guests and features a kitchen, air conditioning, and parking, providing a comfortable and aesthetically pleasing stay.

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Top-Rated Holiday Rentals with a Balcony in Pickering, Canada

Take in beautiful local sunsets directly from the privacy of holiday rentals with balconies in Pickering, Canada.

Modern Townhome W Parking: 10 Min To Boardwalk · Spa · Zoo - Pickering
9.4 3 reviews

Modern Townhome W Parking: 10 Min To Boardwalk · Spa · Zoo

apartment, Toronto
This modern, newly built 2-bedroom townhome in Pickering provides convenient access to the GO Train (800 metres), Frenchman's Bay Lakefront (800 metres), the Toronto Zoo (10 minutes by car), and Thermëa Spa (15 minutes by car).
This property offers 2 bedrooms, 2.5 bathrooms, accommodation for 4 guests, air conditioning, complimentary parking, and high-speed 1 Gbps WiFi, with a kitchen equipped with a fridge, microwave oven, and dishwasher.
Spacious 3 Bedroom Walkout Basement Apartment - Pickering
9.4 20 reviews

Spacious 3 Bedroom Walkout Basement Apartment

apartment, Toronto
This three-bedroom Ajax apartment, situated approximately 5km from the Ajax Convention Centre and Deer Creek Golf Club, offers easy access to the Pickering Casino Resort.
Sleeping six guests, this self-catering property boasts two bathrooms, a fully equipped kitchen including a dishwasher, free Wi-Fi, a Smart TV, on-site parking, and a terrace with garden access; it’s roughly a 30-40 minute drive from Toronto.
King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km From Tesla Chrg - Pickering
10 29 reviews

King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km From Tesla Chrg

apartment, Claremont
This spacious apartment is located in Pickering, a short drive from Claremont, and is within 15 minutes of the Toronto Zoo, Thermea Spa, Frenchman's Bay Marina, and Pickering Casino. It has received excellent user ratings and is perfect for families or groups of up to eight people.
The property offers a generous 195 square metres of living space, with four bedrooms and eight bathrooms. Guests can enjoy a range of amenities including a fully equipped kitchen, a gas fireplace, a 65-inch smart TV, and a private garden, as well as dedicated workspaces and high-speed internet.
Modern Gem| 2026 Fifa - 40 Mins To Bmo Field | Thh - Pickering
9.0 2 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

Homey H*c*man - Pickering
10 7 reviews

Homey H*c*man

apartment, Toronto
This apartment in the Durham region offers a strategic base for exploring Toronto, with convenient access to western attractions and eastern destinations such as Peterborough, Port Hope, and Cobourg.
This one-bedroom flat accommodates up to four guests and features air conditioning, Wi-Fi, and a kitchen equipped with a fridge, freezer, and microwave oven, providing a comfortable retreat after a day of sightseeing.
Ajax Newly Furnished Spacious & Bright 2 Beds. Basement Apart. W/t Own Laundry - Pickering
10 6 reviews

Ajax Newly Furnished Spacious & Bright 2 Beds. Basement Apart. W/t Own Laundry

apartment, Toronto
This private, newly furnished 2-bedroom basement flat in Central Ajax offers a peaceful retreat backing onto the Greenbelt pathway and stream, located 6 kilometres from the 401 highway and Ajax GO Train Station for travel to Toronto.
This self-contained accommodation for up to 4 guests includes its own entrance, air conditioning, dedicated parking, and an in-unit washer and dryer, with a fully equipped kitchen and smart TV in the living area, all within a 10-kilometre drive of Pickering Casino and Pickering Mall.
Luxury & Stylish 3bd | Chefs Kitchen & Cozy - Pickering
9.7 103 reviews

Luxury & Stylish 3bd | Chefs Kitchen & Cozy

apartment, Toronto
This three-bedroom house, situated in Pickering's West Shore neighbourhood, is conveniently located approximately 4.8km from Pickering GO station, Pickering Town Centre, and Highway 401, offering easy access to Toronto Union Station via a 23-minute GO Train journey.
The property boasts a newly renovated chef's kitchen with stainless steel appliances, including a Wolf cooktop, two modern bathrooms, a large smart TV, keyless entry, and two dedicated parking spaces; sleeping six guests comfortably, it's close to Frenchman's Bay for waterside activities.
Studio For Two In Central Pickering - Pickering
9.7 15 reviews

Studio For Two In Central Pickering

studio, Toronto
This studio apartment offers excellent transport links, situated directly opposite Pickering GO Station and a short drive from the M401, with Pickering Town Centre and the Marina within walking distance.
This ground-floor flat, ideal for one guest, features a fully equipped kitchen with a full-size fridge, in-suite laundry with a large washer and dryer, and entertainment including a TV with Fire Stick, all within a 1-bedroom, 1-bathroom layout.

Top Rated Luxury Holiday Rentals in Pickering, Canada

Treat yourself to smart-home features, high-end interiors, and curated artwork at luxury holiday rentals in Pickering, Canada.

Cozy Suite-close To Pickering Casino Resort, Dog Parks, And Waterfront Trail - Pickering
10 10 reviews

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

apartment, Toronto

Top-Rated Downtown Holiday Rentals in Pickering, Canada

Walk to top historic sights, museums, and transport hubs from centrally located holiday rentals in Pickering, Canada.

2 Queen Beds + 1 Sofa-bed - Basement Apt - Pickering
10 18 reviews

2 Queen Beds + 1 Sofa-bed - Basement Apt

apartment, Toronto
Home Away From Home! - Pickering
10 1 review

Home Away From Home!

apartment, Toronto
Comfy 2 Bedroom Near The Beach! - Pickering
9.0 4 reviews

Comfy 2 Bedroom Near The Beach!

apartment, Toronto
Home Away From Home - Pickering
9.3 46 reviews

Home Away From Home

apartment, Toronto
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