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.

King Bed Comfort On Main Floor - Pickering
8.0 1 review

King Bed Comfort On Main Floor

apartment, Toronto
This three-bedroom flat is located in Ajax, a town just east of Toronto, approximately 40 kilometres from the city centre and close to attractions like the Whitby History Museum & Children's Centre and Herongate Barn Theatre. The property has received very good user ratings and an excellent location rating.
The 232 square metre flat has a dedicated workspace, a charming interior, and a garden. It offers a range of amenities including a fully equipped kitchen, air conditioning, a jacuzzi, and parking.
Entire Spacious Private Home Steps To Beach - Pickering
9.5 71 reviews

Entire Spacious Private Home Steps To Beach

bungalow, Toronto
This charming bungalow is located just 25 kilometres from downtown Toronto, in a peaceful neighbourhood close to Rouge Beach and Petticoat Creek Conservation Park, offering stunning lake views and easy access to nature. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom house comfortably accommodates up to four guests and features a fully equipped kitchen, air conditioning, and a private garden. Enjoy relaxing evenings in the tranquil surroundings, or explore the nearby walking trails, restaurants, and attractions.
Ultimate King & Queen,privatebalcony, Freeparking, Wifi, Safe, Stylish - Pickering
9.0 7 reviews

Ultimate King & Queen,privatebalcony, Freeparking, Wifi, Safe, Stylish

apartment, Toronto
This Pickering condominium provides a peaceful suburban retreat with easy access to Toronto's attractions, located near theme parks and waterfront parks such as Rouge National Urban Park, approximately 35 kilometres east of downtown Toronto.
This one-bedroom, one-bathroom flat accommodates up to four guests and features a chef-inspired kitchen, air conditioning, a swimming pool, garden, sauna, spa, and parking, with opportunities for wildlife activities like game walks and birdwatching nearby.
Luxury Ground-level "Suite Escape" - Pickering
9.9 123 reviews

Luxury Ground-level "Suite Escape"

house, Toronto
This guest suite is situated in Pickering, Ontario, just 30-40 minutes from downtown Toronto and Pearson Airport, offering easy access to the city's attractions and amenities. The property has consistently received excellent ratings for its cleanliness, location, and user experience.
The self-contained apartment comfortably accommodates two guests and features a modern design with a queen bed, a spa bathroom with a towel warmer, a fireplace, a designated workstation, a 65” TV, air conditioning, a kitchenette, and parking. Guests can enjoy a peaceful retreat from the city while still being close to major highways, public transportation, and various attractions, including malls, cinemas, casinos, waterfront, hiking trails, golf courses, and wineries.

Best Pickering holiday rentals with parking

The Devineridge Executive House - Pickering
9.9 17 reviews

The Devineridge Executive House

apartment, Toronto
This 2500 sq ft, four-storey detached residence in Ajax offers excellent access to major motorways, placing Toronto and attractions such as the Pickering Casino Resort and Deer Creek Golf Club within easy reach.
This property features three bedrooms, four bathrooms, and accommodation for six guests, with amenities including a fully equipped modern kitchen, two distinct living areas, a dedicated workspace, private balcony, and a garden patio, plus parking for three vehicles.
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.
Beautiful One Bedroom Basement Apartment - Pickering
No reviews

Beautiful One Bedroom Basement Apartment

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.
2br Basement W Parkin Near Transit,shoppin,nature - Pickering
9.1 13 reviews

2br Basement W Parkin Near Transit,shoppin,nature

apartment, Toronto
This basement flat is located in a quiet residential neighbourhood in Northeast Ajax, just a short drive from major highways, shopping centres and public transport links. The property has received excellent ratings for its location, cleanliness and overall experience.
The self-contained flat can sleep up to five guests and features a comfortable living space with a well-equipped kitchen, a private entrance and access to a shared patio. Guests can enjoy a 58" TV with streaming services, air conditioning and a private garden.

Frequently asked questions about holiday rentals in Pickering

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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.

Cosy 3-bedroom Home In Quiet Cul-de-sac. - Pickering
9.7 196 reviews

Cosy 3-bedroom Home In Quiet Cul-de-sac.

house, Toronto
This comfortable 3-bedroom house is located in Pickering, a quiet suburb just 12km from the Toronto Zoo, 29km from the Ontario Science Centre, and 37km from the Royal Ontario Museum. The property has received excellent ratings for location, cleanliness, and user experience.
The house spans 139 square metres and comfortably accommodates up to 6 guests. This family-friendly house offers a range of amenities, including a fully-equipped kitchen, a terrace, a garden, a sauna, a spa, a fitness centre, and private parking.
Home Away From Home! - Pickering
10 1 review

Home Away From Home!

apartment, Toronto
This Pickering flat offers convenient access to Toronto attractions, situated approximately 12.5 kilometres from the Toronto Zoo and 37 kilometres from Yonge-Dundas Square.
This one-bedroom flat, measuring 37 square meters, accommodates up to three guests and features a private balcony, complimentary WiFi, private parking, and a kitchenette, with the Toronto Zoo a mere 12.5 kilometres away.
Detached 3 Br Home In Ajax,on - Pickering
9.5 135 reviews

Detached 3 Br Home In Ajax,on

apartment, Toronto
This four-bedroom home is located in a peaceful suburban area, just 12 miles from the Toronto Zoo and 26 miles from the Ontario Science Centre. The property has received excellent ratings for its cleanliness, location, and overall experience.
The spacious 158 square metre apartment can comfortably accommodate up to eight guests. Amenities include a fully equipped kitchen, a private garden, free parking, and free Wi-Fi, making it ideal for families or groups looking for a comfortable and convenient stay.
Stylish 3 Br Apt W/ Free Parking, Wifi & Patio - Pickering
10 2 reviews

Stylish 3 Br Apt W/ Free Parking, Wifi & Patio

apartment, Oshawa
This three-bedroom Whitby apartment, a 13-minute walk (approx. 2km) from the Whitby Museum and Children's Centre, offers easy access to Lake Ontario (8km) and Darlington Provincial Park.
Sleeping six guests, this self-catering property boasts a fully equipped kitchen, Wi-Fi, air conditioning, a private balcony, garden, on-site parking, and a workspace; nearby attractions include the Ontario Regiment Museum and Lynde Shores Conservation Area.

Best Pickering holiday rentals with air conditioning

Guest Suite In Whitby - Pickering
9.8 114 reviews

Guest Suite In Whitby

apartment, Oshawa
This two-bedroom flat is situated in Whitby, a short drive from Oshawa and within easy reach of attractions like the Toronto Zoo and Ontario Science Centre. The property enjoys excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The 950 square metre flat comfortably accommodates up to four guests and includes a fully equipped kitchen with a fridge, microwave oven, and dishwasher. Amenities include air conditioning, free parking, and free Wi-Fi, ensuring a comfortable and convenient stay.
Luxury Lakeview Condo  Steps To Sandy Beach - Pickering
9.8 12 reviews

Luxury Lakeview Condo Steps To Sandy Beach

apartment, Toronto
This modern flat offers a peaceful retreat near Sandy Beach, just a 5-minute walk from the GO Station and minutes from Pickering Town Centre, with straightforward travel to downtown Toronto.
This one-bedroom condo accommodates two guests and features air conditioning, a garden, a fitness centre, parking, and a well-equipped kitchen including a fridge, freezer, microwave, and dishwasher, ideal for couples or solo travellers.
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.
Main Floor Bright Modern 1 Bedroom - Pickering
10 1 review

Main Floor Bright Modern 1 Bedroom

apartment, Toronto
This Pickering flat offers a private entrance and a full main floor balcony, situated in a quiet, family-friendly neighbourhood just 500 metres from local parks and within easy reach of GO Transit and Durham Bus services for convenient travel across the Greater Toronto Area.
This one-bedroom, one-bathroom flat accommodates two guests and includes on-site laundry, parking, air conditioning, and a kitchen with a fridge, ensuring a comfortable stay with excellent transit connectivity and proximity to shops and amenities.

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.

Luxury & Stylish 3bd | Chefs Kitchen & Cozy - Pickering
9.7 103 reviews

Luxury & Stylish 3bd | Chefs Kitchen & Cozy

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

Comfy 2 Bedroom Near The Beach!

apartment, Toronto
Spacious Basement Lower Suite 3br Home Stay 1 King 2 Queen Beds 2 Car Parkings Fifa 2026 - Pickering
9.2 14 reviews

Spacious Basement Lower Suite 3br Home Stay 1 King 2 Queen Beds 2 Car Parkings Fifa 2026

apartment, Toronto
Apartment In Pickering - Pickering
9.8 8 reviews

Apartment In Pickering

apartment, Toronto
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