Compare vacation rentals in Pickering from 100+ sites!
1167 available vacation rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Vacation rentals and Airbnb offers in Pickering
8.0 1 review
Pickering
07/30 – 08/05
$212/nighttotal: $1272 (6 )
Full House Steps To Beach Pickering | 3br Sleeps 6
1 2
apartment , Toronto
This 1930s cottage is located in Pickering, a 45-minute train ride from downtown Toronto, offering direct access to the waterfront trail and proximity to the beach, boardwalk, cafés, and restaurants. This 3-bedroom, 1-bathroom rental accommodates up to 6 guests and features a separate media room, air conditioning, internet, a kitchen, and parking for two cars.
9.8 136 reviews
Pickering
06/20 – 06/21
$479/nightfor 1 night
Serene Stays - Pickering (5beds, 2.5baths, 4park)
1 10
apartment , Oshawa
This spacious Pickering house, a 15-23 minute drive from the Toronto Zoo and Pickering Casino Resort, offers convenient access to area attractions. The 4-bedroom, 2-bathroom home sleeps 10, features a fully equipped kitchen with dishwasher, high-speed internet (up to 2.5 Gbps), in-unit laundry, and four parking spaces; a crib and high chair are available for families.
10 6 reviews
Pickering
07/10 – 07/12
$217/nighttotal: $434 (2 )
Lake Breeze Apartment, Ev Charging & Free Parking
2 2
apartment , Toronto
This two-bedroom basement rental is located in Ajax, Ontario, a beachfront community on Lake Ontario, approximately a 30-minute drive from Toronto and close to attractions like the Toronto Zoo and Whitby's museums. The 2-bedroom unit, which sleeps four, features a full kitchen with a refrigerator, microwave, and dishwasher, air conditioning, a garden, and access to a fitness center; guests can enjoy birdwatching and nearby lake activities.
9.8 8 reviews
Pickering
08/22 – 09/02
$261/nighttotal: $2871 (11 )
The Devineridge Executive House
1 4
apartment , Toronto
This spacious detached home is located in a quiet, family-friendly neighborhood in Ajax, Ontario, offering convenient access to Highways 401/407/412 and proximity to shopping, dining, and the Pickering Casino Resort. This 4-story residence features 3 bedrooms, 4 bathrooms, accommodates up to 6 guests, and includes a modern kitchen, private balcony, backyard patio, and secure parking for 3 vehicles.
10 7 reviews
Pickering
06/20 – 06/27
$120/nighttotal: $840 (7 )
Cozy Suite-close To Pickering Casino Resort, Dog Parks, And Waterfront Trail
1 2
apartment , Toronto
This Ajax, Ontario basement apartment offers easy access to Deer Creek Golf Course and Lake Ontario, a short drive from Toronto attractions like the Toronto Zoo and Rouge National Urban Park. The one-bedroom, one-bathroom unit sleeps three guests and features a kitchenette with a refrigerator and microwave, air conditioning, parking, and a private entrance; enjoy nearby golf, nature trails, and easy access to Toronto.
9.9 78 reviews
Pickering
07/10 – 07/12
$199/nighttotal: $398 (2 )
Cheery 1941 Historic Home In Ajax
1 2
apartment , Toronto
This cozy historic house is located in a quiet neighborhood in Ajax, just a short drive from Toronto, with easy access to the Go Train, Highway 401, and various amenities. The house has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The house offers two bedrooms and one bathroom, accommodating up to four guests. Enjoy the convenience of a fully equipped kitchen, a private backyard with a BBQ, a gym room, and access to a washer and dryer for stays of five nights or more.
9.6 17 reviews
Pickering
08/22 – 09/02
$121/nighttotal: $1331 (11 )
Bright & Cozy Basement Apartment
1 4
apartment , Toronto
This brand-new two-bedroom, two-bathroom basement apartment in Ajax, Ontario, offers convenient access to Toronto attractions such as the Toronto Zoo (20-minute drive), Ajax Outlets, and major highways (401, 407). The 2-bedroom rental features a private kitchen, laundry facilities, a queen-size bed and a futon, accommodating up to 5 guests, and is close to golf courses, a racetrack, and casinos.
9.7 106 reviews
Pickering
07/01 – 07/31
$246/nighttotal: $7380 (30 )
Newly Renovated, 3 Bdrm Modern Oasis W/ Parking!!!
1 5
house , Oshawa
This luxurious townhome is located just outside of Downtown Whitby, minutes from Highway 401 and 407, making it easy to explore the Greater Toronto Area. It has received excellent ratings for location, cleanliness, and overall user experience. This spacious home offers 1900 square feet of living space, perfect for families or groups of friends, with a capacity of up to 8 guests. The fully equipped kitchen includes a fridge, freezer, microwave, dishwasher, kettle, and coffee machine, and each bathroom is stocked with shampoo, conditioner, body wash, and a blow dryer.
10 4 reviews
Pickering
06/20 – 06/27
$548/nighttotal: $3836 (7 )
Lakeside Luxe
3 2
apartment , Toronto
This Pickering vacation rental, near Frenchman's Bay, offers easy access to attractions like the Herongate Barn Theatre and Scarborough Historical Museum, and is a short drive from the Toronto Zoo and several conservation areas including Lynde Shores. This three-bedroom, three-bathroom home sleeps six and features a gourmet kitchen, spacious living areas, a relaxing deck, and modern amenities.
9.9 14 reviews
Pickering
07/28 – 08/11
$198/nighttotal: $2772 (14 )
Spacious Ravine-view Escape-bsmt
1 4
apartment , Toronto
This two-bedroom, two-bathroom Toronto apartment rental in the Rouge Hill neighborhood offers convenient access to the Rouge Hill GO station, Highway 401, and Port Union Waterfront Park. The 2-bedroom unit features a modern, open-concept layout, in-unit laundry, free Wi-Fi, parking, air conditioning, and stunning ravine views from a private patio; it comfortably sleeps five guests and is near many Toronto attractions.
Pickering
06/20 – 06/27
$105/nighttotal: $735 (7 )
Pinnacle Of Luxury & Leisure -1 Bedroom With Washroom | Shared Full Kitchen
1 1
apartment , Oshawa
This newly constructed legal basement suite is located in Whitby, offering convenient access to Herber-Down Conservatory, Durham College, and Ontario Tech University, and is a short drive from Lake Ridge Ski Resort. This one-bedroom, one-bathroom apartment accommodates one guest and features air conditioning, high-speed Wi-Fi, a 65-inch Smart TV with IPTV, and a spa-like shower, with a shared full kitchen available.
10 3 reviews
Pickering
07/30 – 08/05
$104/nighttotal: $624 (6 )
A Homely Inn
1 2
apartment , Toronto
This one-bedroom, one-bathroom rental unit is located in Rouge Hill, eastern Scarborough, offering direct access to Rouge National Urban Park and convenient proximity to major highways. This duplex provides air conditioning, internet, a kitchen, and parking for up to two guests, with opportunities for hiking, paddling, and wildlife viewing in the nearby Rouge Valley and Toronto Zoo.
Top Vacation Rentals for Families in Pickering
These family-friendly vacation rentals in Pickering offer spacious layouts and easy access to top city attractions.
10 2 reviews
Pickering
08/21 – 09/07
$547/nighttotal: $9299 (17 )
Entire Home | Toronto Hub | Therma Spa | 12 Guests | Dagmar | Sports Arenas
6 2
apartment , Oshawa
This spacious Whitby apartment, a six-minute drive from Lake Ontario and three minutes from the Whitby Museum & Children's Centre, offers easy access to Oshawa attractions. The 3,000-square-foot rental boasts six bedrooms, five bathrooms, sleeps twelve, and includes amenities such as Wi-Fi, parking, and a fully equipped kitchen.
9.2 56 reviews
Pickering
08/14 – 08/29
$160/nighttotal: $2400 (15 )
Private 2bedroom Unit, Free Parking, Free From Smoke & Pet, Self-check In
2 2
apartment , Toronto
This Pickering rental is conveniently located about 16 kilometers from the Toronto Zoo and roughly 42 kilometers from downtown Toronto attractions such as the Distillery District and Ryerson University. This 700-square-foot apartment features two bedrooms, one bathroom, and accommodates up to 11 guests, offering free Wi-Fi, in-unit laundry, a fully equipped kitchen, private parking, and a garden.
10 2 reviews
Pickering
06/25 – 06/27
$246/nighttotal: $492 (2 )
Stylish 3 Br Apt W/ Free Parking, Wifi & Patio
1 2
apartment , Oshawa
This fully furnished 3-bedroom Whitby basement apartment, located 3 minutes from downtown Whitby's restaurants and shops and 6 minutes from both the Whitby GO Station and Port Whitby Marina, offers easy access to Toronto and Oshawa attractions. The 3-bedroom rental boasts a private entrance, self check-in, free parking for two cars, a private patio, a fully equipped kitchen with complimentary coffee, a washer/dryer, central heating and air conditioning, a smart TV with streaming apps, and accommodates up to 6 guests.
9.8 23 reviews
Pickering
07/01 – 07/31
$360/nighttotal: $10800 (30 )
Mid-century Modern Castle | King Bed+free Parking
1 5
apartment , Toronto
This Ajax, Ontario rental property, near Highway 401, the GO Train station, a casino, and Lake Ontario, offers convenient access to Toronto attractions. This three-bedroom, three-bathroom home sleeps up to ten guests and features a fully equipped kitchen, high-speed Wi-Fi, a spacious living area with a large flat-screen TV, and ample parking for two vehicles.
Best Pickering vacation rentals with parking
9.5 281 reviews
Pickering
08/26 – 11/25
$68/nighttotal: $6188 (91 )
Lovely Studio Apartment With Easy Access To City
1 2
studio , Toronto
This studio apartment is located in a residential neighborhood in Toronto, just a short walk from local shops and restaurants. The studio features a spacious open-concept layout that can comfortably accommodate three guests with a queen bed and a futon, and includes a private entrance, air conditioning, a fully equipped kitchen with a fridge, freezer, and microwave, and laundry facilities available upon request.
9.9 416 reviews
Pickering
07/10 – 07/12
$140/nighttotal: $280 (2 )
“Elysium” Where Happiness Is Real!
1 2
apartment , Toronto
This basement suite is located in Pickering, a suburb east of Toronto, just a short drive from the Toronto Zoo, Pickering Casino, and Pickering Town Centre. The apartment has received excellent ratings for user experience, location, and cleanliness. This private, walk-out basement suite can comfortably accommodate two guests and features a separate street and building access for privacy. Guests can enjoy amenities such as free parking, Bell Fibe wifi, a TV with 1000+ streaming channels, an iPad to control the temperature, and laundry access for stays of 5 nights or longer.
9.9 55 reviews
Pickering
10/20 – 04/27
$68/nighttotal: $12852 (189 )
Quiet Upscale Neighbourhood
1 2
apartment , Toronto
This Toronto apartment rental near Rouge National Urban Park and Rouge Beach offers easy access to downtown via the GO train and major highways. The one-bathroom unit sleeps four guests and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus in-suite laundry, TVs in the living room and bedroom, and private parking.
Pickering
06/23 – 07/23
$142/nighttotal: $4260 (30 )
New High End Finishing Apartment
2 4
apartment , Toronto
This 2-bedroom apartment is located in Scarborough, just a short distance from the University of Toronto Scarborough, Colonel Danforth Park, Morningside Park, and Lake Ontario. The quiet neighborhood offers a peaceful setting away from the bustling downtown core. The unit features a kitchen and shower, and can comfortably accommodate up to 28 guests. You'll also have access to parking, internet, air conditioning, and a smoke-free environment.
Frequently Asked Questions about vacation rentals 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, like spring and fall. The weather is still pleasant, and the crowds are smaller. You'll also find better deals on rentals during these times.
What are the best Airbnb and vacation rentals in Pickering?
What are the best budget-friendly activities in Pickering?
Pickering offers a lot of free activities, like exploring the Rouge National Urban Park or taking a walk along the waterfront. You can also check out the Pickering Museum Village, which offers free admission on Tuesdays.
What are the best restaurants with local dishes in Pickering?
For a taste of local cuisine, try the Pickering Village Restaurant. They offer a variety of dishes, including Canadian comfort food. Another option is the Pickering Fish Market, which serves fresh seafood.
What are the best vacation rentals with a pool 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 shores of Lake Ontario. It offers scenic views of the lake and the city. You can also check out the Rouge National Urban Park, which has a variety of hiking trails.
What are the best rentals for families and kids in Pickering?
Yes, the Rouge National Urban Park is pet-friendly. You can bring your furry friend for a walk on the trails or a swim in the lake. Many restaurants also have outdoor patios that are pet-friendly.
What are the best rentals or Airbnbs with a jacuzzi in Pickering?
What are the benefits of choosing a vacation rental in Pickering?
Vacation rentals offer more space and privacy than a hotel room. They are often located in residential areas, which gives you a more authentic experience of the city. They can also be more affordable than hotels, especially for families or groups.
What are the top sports attractions and facilities in Pickering?
The Pickering Recreation Complex is a popular spot for sports and recreation. It has an indoor pool, fitness center, and ice rink. The city also has several parks and fields for outdoor sports.
Destinations nearby
Best Vacation Rentals with Balconies in Pickering
Wake up to breathtaking views at these Pickering vacation rentals with balconies, perfect for your morning coffee.
Pickering
10/10 – 10/16
$333/nighttotal: $1998 (6 )
Modern 4bedroom Retreat I 2car Parking I Steps From The Ajax Waterfront
4 4
apartment , Toronto
This 4-bedroom house in Ajax, Toronto, is located a 1-minute drive from Ajax Waterfront Park and Lake Ontario, offering 5-minute drive access to the Ajax GO Station for transit. This home accommodates up to 9 guests with 3 bathrooms, a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, a balcony, and is near retailers like Costco and Walmart.
Pickering
07/10 – 07/12
$116/nighttotal: $232 (2 )
One Bedroom Apartment
1 2
apartment , Toronto
This one-bedroom rental unit is situated in Ajax, approximately 30 miles east of downtown Toronto's core attractions, including the Distillery District and the University of Toronto. This 170 square foot studio apartment accommodates two guests and offers complimentary WiFi, air conditioning, and free private parking, with a kitchenette featuring a microwave and toaster.
Pickering
08/26 – 11/25
$93/nighttotal: $8463 (91 )
2-bedroom Plus Den Condo In Enjoyable Toronto With Wifi, Ac
2 2
apartment , Toronto
This Scarborough, Toronto vacation rental is a 12-minute walk from Morningside Park and a 3-minute drive from Lake Ontario, offering easy access to attractions like Guild Inn Gardens and Colonel Danforth Park. The two-bedroom, two-bathroom apartment comfortably sleeps five guests and includes Wi-Fi, air conditioning, and in-unit laundry; nearby amenities include the Scarborough Town Centre and the Toronto Zoo.
9.8 25 reviews
Pickering
08/22 – 09/02
$154/nighttotal: $1694 (11 )
Love And Relax At Dream Catcher Retreat
1 4
apartment , Oshawa
This comfortable one-bedroom apartment is conveniently located in Whitby, just outside of Oshawa, a 25-minute drive from the Toronto Zoo and 42 minutes from the Ontario Science Centre. Guests consistently rate the apartment as excellent for cleanliness, location, and overall experience. The 750-square-foot apartment comfortably sleeps up to six guests and includes a well-equipped kitchen, a private garden, and a modern bathroom. Enjoy amenities like air conditioning, a dishwasher, an outdoor fireplace, and a convenient on-site cafe, all within easy reach of Lake Ontario's natural beauty.
Best Pickering vacation rentals with air conditioning
9.5 11 reviews
Pickering
06/20 – 06/21
$486/nightfor 1 night
Embers Nest - 5 Beds, 4 Bath, 2 Park, Thermea Spa
1 10
apartment , Oshawa
This Oshawa townhouse offers a prime location in Whitby, with easy access to dining, shopping, and entertainment, and is situated 9 miles from Heber Down Conservation Area and 17 miles from Lynde Shores Conservation Area. This family-friendly rental accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, featuring a private backyard, a dedicated workspace, in-unit laundry, free parking for two vehicles including garage access, and a master suite with a standing shower and soaker tub.
9.7 13 reviews
Pickering
06/23 – 07/23
$117/nighttotal: $3510 (30 )
Modern 2br Suite | One Free Parking & Wifi
1 4
apartment , Toronto
This brand-new basement apartment rental in Ajax, Ontario, offers easy highway access for convenient commutes to Toronto and its attractions. The fully furnished 2-bedroom, 1-bathroom unit sleeps four guests and includes a full kitchen, air conditioning, and parking; nearby shops and restaurants provide additional convenience.
9.8 9 reviews
Pickering
10/10 – 10/16
$157/nighttotal: $942 (6 )
Beautiful 3bedroom Home Away From Home In Ajax
1 5
apartment , Toronto
This 3-bedroom, 1-bathroom condo is located in a quiet Toronto neighborhood, offering a peaceful retreat less than 5 miles from the CN Tower and Ripley's Aquarium of Canada. This apartment accommodates up to 6 guests and features air conditioning, internet, a kitchen, and parking, with easy access to public transport and renowned dining and shopping areas.
9.7 91 reviews
Pickering
07/01 – 07/31
$288/nighttotal: $8640 (30 )
Luxury & Stylish 3bd | Chefs Kitchen & Cozy
1 5
apartment , Toronto
This three-bedroom house rental in Pickering's West Shore neighborhood is conveniently located three minutes from the GO station, Pickering Town Centre, and Highway 401, offering easy access to downtown Toronto (23 minutes to Union Station via GO). The 3-bedroom, 2-bathroom home features a newly renovated chef's kitchen with stainless steel appliances (including a Wolf cooktop), a spacious living room with a smart TV, high-speed Wi-Fi, two driveway parking spots, and proximity to Frenchman's Bay for lakefront activities; it comfortably sleeps six guests.