Find short term rentals in Pickering at the best prices

1428 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Pickering short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Pickering

Best Pickering luxury short term rentals

Room In Ajax With En-suite Washroom - Pickering
9.8 137 reviews

Room In Ajax With En-suite Washroom

apartment, Toronto
This charming bed and breakfast is situated just 2 kilometres from the intersection of Highways 401 and 412, close to a shopping district, offering easy access to both downtown Toronto and surrounding areas. It has consistently received excellent ratings for its location, cleanliness and overall experience.
The guesthouse has one bathroom and can accommodate up to two guests. It features high-speed Wi-Fi, a designated workspace, and on-site parking, making it ideal for both leisure and business travellers.

Best Pickering Short term rentals with a jacuzzi

Among the 1428 accommodations in Pickering, here are the 4 best rentals with a jacuzzi

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.
Assets Event Venue Modern Interior With Elegant Décor. - Pickering
9.2 16 reviews

Assets Event Venue Modern Interior With Elegant Décor.

apartment, Oshawa
This spacious six-bedroom house is located in north Whitby, a 45-minute drive north of downtown Toronto, offering a tranquil escape from the city. It has received excellent user ratings, making it a popular choice for travellers.
The property features a private pool, hot tub, and gym, along with a fully equipped kitchen and five bathrooms. It can accommodate up to 20 guests, making it perfect for large families or groups of friends. Guests can enjoy a variety of amenities including a garden, spa, and concierge services, as well as access to nearby attractions such as golf courses, botanical gardens, and wineries.
2 King Beds Hot Tub Parking Dt Whitby 401/ Go - Pickering
10 2 reviews

2 King Beds Hot Tub Parking Dt Whitby 401/ Go

apartment, Oshawa
This ground-floor flat in downtown Whitby offers proximity to amenities and public transport, being a 5-minute walk to local cafés, restaurants, breweries, shops, and a 5-minute drive to Whitby GO Station and the Highway 401.
This two-bedroom, one-bathroom apartment accommodates up to four guests and features a private backyard with a hot tub, fire pit, BBQ, a fully equipped kitchen, a dedicated workspace, and entertainment options including a record player and Smart TVs, all within an hour's drive of Toronto attractions.
Hot Tub Oasis | 35 Min To Dt | Main Floor Suite - Pickering
9.8 329 reviews

Hot Tub Oasis | 35 Min To Dt | Main Floor Suite

B&B, Toronto
This charming guest suite is located just 7km from the 401/407 highway interchange and train station, making it easy to explore Toronto and its surrounding areas. The property has received excellent ratings for its cleanliness, location, and overall experience.
The self-contained suite is situated on the main floor and can accommodate up to two guests. It comes equipped with a fireplace, free parking, internet, cable, air conditioning, a fridge, Keurig, tea kettle, microwave, induction burner, air fryer, and laundry access.

Frequently Asked Questions about short term rentals in Pickering

Popular destinations

Best family friendly Pickering Short term rentals

Among the 1428 accommodations in Pickering, here are the 4 best family friendly rentals

Discover The Perfect Fusion Of Style And Comfort Your Home Away From Home. - Pickering
9.2 9 reviews

Discover The Perfect Fusion Of Style And Comfort Your Home Away From Home.

apartment, Toronto
This four-bedroom, three-bathroom flat is situated in the South Ajax district, offering proximity to natural areas such as Lynde Shores Conservation Area and Oshawa Valley Botanical Gardens, and is approximately 30 kilometres east of downtown Toronto.
This spacious 204 square metre residence, suitable for up to eight guests, features a newly renovated open-concept kitchen with modern appliances, air conditioning, Wi-Fi, and provides access to a garage space and the backyard.
Lovely Garden View Private Apartment With Patio - Pickering
9.4 135 reviews

Lovely Garden View Private Apartment With Patio

B&B, Toronto
This comfortable apartment is situated in a peaceful residential neighbourhood in Pickering, a suburb of Toronto, just 15 kilometres from the Beachfront Park and 10 kilometres from Pickering Town Centre. The property consistently receives excellent ratings for cleanliness, location and overall guest experience.
The apartment has a modern, open-plan design with a well-equipped kitchen and a cosy living area, comfortably accommodating up to three guests. Enjoy a private, fenced backyard, a fully equipped kitchen, a washing machine and dryer, free parking and high-speed internet, perfect for relaxing and exploring the area.
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.
Luxury & Stylish 3bd | Chefs Kitchen & Cozy - Pickering
9.7 97 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.

Best Pickering lodging with parking

Home Away Home - Pickering
10 51 reviews

Home Away Home

apartment, Toronto
This three-bedroom Toronto property, sleeping five, is located 1.5km from Pickering Beach and a 5-minute drive from the highway, offering easy access to the Ancient Spirit Garden and several parks.
The self-catering house boasts a fully equipped kitchen with fridge, microwave, and dishwasher, air conditioning, a garden, parking, and excellent guest reviews, making it perfect for family getaways near Toronto.
Modern Cozy Living. - Pickering
9.8 66 reviews

Modern Cozy Living.

apartment, Toronto
This private Toronto basement apartment, ideal for families, offers peace and quiet in a residential area; further details on its precise neighbourhood and proximity to landmarks are needed for a complete location assessment.
The two-bedroom, two-bathroom flat sleeps four guests and includes a kitchen equipped with a fridge, microwave, and dishwasher, plus keyless entry and backyard access.
Paris Cafe: Modern Bsmt 3b/1b, Kitchen & 3 Parking - Pickering
9.3 36 reviews

Paris Cafe: Modern Bsmt 3b/1b, Kitchen & 3 Parking

B&B, Toronto
This two-bedroom basement flat in Pickering, Ontario, offers convenient access to the Toronto Zoo (approximately 25km away) and Frenchman's Bay Marina, bordering Scarborough and close to the 401 highway.
The 2-bathroom property sleeps up to 7 guests, features a fully equipped kitchen, high-speed internet, dedicated parking, and a separate entrance; nearby attractions include Petticoat Creek Conservation Park.
Cozy 2-bedroom With Kitchen - Pickering
9.9 18 reviews

Cozy 2-bedroom With Kitchen

apartment, Toronto
This spacious Toronto basement flat is conveniently located near a highway, offering easy access to Toronto city centre, approximately 56km away.
The 111 sqm self-contained unit sleeps four guests, boasting two bedrooms, one bathroom, a kitchen, air conditioning, internet access, and three off-street parking spaces with CCTV surveillance.
©2026 cozycozy.com