Holiday Rentals in Pickering

1167 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
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

The Continental: Luxury 6b/3.5b + Tesla Charger - Pickering
10 6 reviews
Pickering
01/07 – 31/07
NZ$702/nighttotal: NZ$21060 (30 )

The Continental: Luxury 6b/3.5b + Tesla Charger

1 5
apartment , Oshawa
This spacious four-bedroom, three-and-a-half-bathroom flat is situated in Whitby, Ontario, a brief 3.5 kilometre drive from Thermëa Spa and conveniently positioned for access to Petticoat Creek Conservation Park and Lynde Shores Conservation Area.
This family-friendly apartment offers accommodation for up to 12 guests, featuring two living areas, a chef's kitchen, air conditioning, a garden, complimentary parking, and an electric car charger.
A Beautiful Walkout Basement - Pickering
8.8 3 reviews
Pickering
14/08 – 29/08
NZ$242/nighttotal: NZ$3630 (15 )

A Beautiful Walkout Basement

3 2
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.
Bright Studio - Pickering
10 1 review
Pickering
26/08 – 25/11
NZ$82/nighttotal: NZ$7462 (91 )

Bright Studio

1 2
apartment , Toronto
This centrally located flat offers a peaceful and secure base, with convenient access to major motorways for travel across the region and excellent connectivity to both Toronto and the Durham area.
This one-bedroom flat accommodates two guests and includes a kitchen with a fridge, freezer, and microwave, plus air conditioning and Wi-Fi, with a garden also available.
Ultra-modern Luxury Retreat! Close To Thermea Spa. - Pickering
10 132 reviews
Pickering
14/08 – 29/08
NZ$237/nighttotal: NZ$3555 (15 )

Ultra-modern Luxury Retreat! Close To Thermea Spa.

1 2
apartment , Toronto
This one-bedroom apartment is located in Ajax, a suburb of Toronto, just a short drive from Thermea Spa and within walking distance of local amenities. It has received excellent ratings for location, cleanliness, and user experience.
The apartment comfortably accommodates two guests and features a modern open-plan layout with a fully equipped kitchen, a private patio, and a separate entrance. Guests can enjoy amenities such as high-speed internet, in-floor heating, a Sonos music system, and a wine fridge, making it an ideal choice for a relaxing and comfortable stay.

Best Pickering holiday rentals with parking

Quiet Upscale Neighbourhood - Pickering
9.9 55 reviews
Pickering
20/10 – 27/04
NZ$117/nighttotal: NZ$22113 (189 )

Quiet Upscale Neighbourhood

1 2
apartment , Toronto
This Toronto apartment is conveniently located near Rouge National Urban Park and Rouge Beach, offering easy access to the GO train for a straightforward commute to the city centre.
The self-contained flat, sleeping up to four guests, boasts a fully equipped kitchen, private bathroom, laundry facilities, two TVs, and private parking, all within a quiet neighbourhood.
City Comfort Meets Nature  Walk To Lake & Trails - Pickering
Pickering
23/06 – 23/07
NZ$341/nighttotal: NZ$10230 (30 )

City Comfort Meets Nature Walk To Lake & Trails

3 4
apartment , Toronto
This three-bedroom flat is located in the Scarborough district of Toronto, offering convenient access to local amenities and a reasonable distance from downtown attractions such as the Hockey Hall of Fame and the Royal Ontario Museum.
This furnished apartment accommodates up to six guests and includes a microwave, dishwasher, air conditioning, and free three-car parking, with the basement area excluded for privacy.
Lakeside Luxe - Pickering
10 4 reviews
Pickering
20/06 – 27/06
NZ$943/nighttotal: NZ$6601 (7 )

Lakeside Luxe

3 2
apartment , Toronto
This three-bedroom, three-bathroom Pickering holiday home is situated near Frenchman's Bay, offering easy access to attractions such as the Herongate Barn Theatre and Scarborough Museum, and is within a variable distance of the Toronto Zoo (distances depend on exact location within Pickering).
The spacious property features a family room, living room, elegant dining area, well-appointed kitchen, and a relaxing deck with tree views, accommodating up to six guests and providing modern comforts for a relaxing stay near Toronto.
Private 2 Bedroom Unit, Private Entry, 2 Parking- Pet/smoke Free - Pickering
Pickering
10/07 – 12/07
NZ$413/nighttotal: NZ$826 (2 )

Private 2 Bedroom Unit, Private Entry, 2 Parking- Pet/smoke Free

2 2
apartment , Toronto
This Pickering apartment, situated near Highway 401, is 2.3km from Pickering beaches, 1.7km from the Pickering Casino, and 9.3km from the Toronto Zoo, offering easy access to major attractions and Downtown Toronto (33km away).
The 74 square metre self-contained flat features two bedrooms, one bathroom, sleeps six guests, includes parking, Wi-Fi, and a kitchen with a fridge and microwave; laundry facilities are available for stays of two nights or more.

Frequently asked questions about holiday rentals in Pickering

Destinations nearby

Best Pickering holiday rentals with a balcony

Stylish 3 Br Apt W/ Free Parking, Wifi & Patio - Pickering
10 2 reviews
Pickering
22/08 – 02/09
NZ$400/nighttotal: NZ$4400 (11 )

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

1 4
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.
Scarborough Oasis Near Uoft Campus, Free Parking - Pickering
Pickering
14/08 – 29/08
NZ$536/nighttotal: NZ$8040 (15 )

Scarborough Oasis Near Uoft Campus, Free Parking

1 2
apartment , Toronto
This Scarborough flat is located 8.4 kilometres from the Toronto Zoo and 14.5 kilometres from the Ontario Science Centre, with key attractions such as the Distillery District and Ryerson University situated 20.9 kilometres away.
This self-catering apartment offers free WiFi, air conditioning, a private balcony, and private parking for up to three guests, with a fully equipped kitchen and one bathroom.
Modern 4bedroom Retreat I 2car Parking I Steps From The Ajax Waterfront - Pickering
Pickering
10/10 – 16/10
NZ$574/nighttotal: NZ$3444 (6 )

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

4 4
apartment , Toronto
This modern 4-bedroom house is located in Ajax, just 160 metres from Lake Ontario and the Ajax Waterfront Park, an 8-minute drive from Pickering Casino Resort and a 5-minute drive from Ajax GO Station.
This spacious 9-person residence features air conditioning, a kitchen equipped with a fridge, microwave oven, and dishwasher, a terrace/balcony, a spa, and parking, with a main-floor bedroom and bathroom ideal for families and close proximity to major retailers.
Furnished Family Home Near Toronto - Great Location Game Room - Backyard - Parking & Self Checkin - Pickering
9.3 18 reviews
Pickering
10/10 – 16/10
NZ$495/nighttotal: NZ$2970 (6 )

Furnished Family Home Near Toronto - Great Location Game Room - Backyard - Parking & Self Checkin

3 4
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 air conditioning

Brand New 2 Bedroom Basement Apartment - Pickering
8.6 16 reviews
Pickering
25/06 – 27/06
NZ$263/nighttotal: NZ$526 (2 )

Brand New 2 Bedroom Basement Apartment

2 2
apartment , Toronto
This recently renovated two-bedroom basement flat in Ajax, Ontario, is situated approximately 18 kilometres from the Toronto Zoo, 35 kilometres from the Ontario Science Centre, and 45 kilometres from both the Distillery District and Ryerson University.
The 12-square-metre self-catering property sleeps seven guests and features two bathrooms, free Wi-Fi, private parking, and a fully equipped kitchen; on-site car rental is available for exploring the wider Toronto area.
Entire 2 Storey Home 1bdrm Private - Pickering
10 44 reviews
Pickering
10/07 – 12/07
NZ$343/nighttotal: NZ$686 (2 )

Entire 2 Storey Home 1bdrm Private

1 2
apartment , Toronto
This Pickering semi-detached house offers easy access to the 401, Toronto Zoo, and downtown Toronto, situated conveniently near shops, restaurants, and grocery stores.
This one-bedroom flat accommodates two guests and features air conditioning, Wi-Fi, a kitchen with a fridge, freezer, and microwave, plus off-street parking, providing a private, two-storey home experience in a quiet neighbourhood.
Bright & Cozy Basement Apartment - Pickering
9.6 17 reviews
Pickering
22/08 – 02/09
NZ$207/nighttotal: NZ$2277 (11 )

Bright & Cozy Basement Apartment

1 4
apartment , Toronto
This brand new self-catering basement flat in Ajax, Ontario, is situated approximately 32 kilometres east of Toronto, offering easy access to the Toronto Zoo and various conservation areas.
The two-bedroom, two-bathroom property sleeps five guests and includes a private kitchen, laundry facilities, and a living room with a sofa bed; nearby attractions include the Outlet Collection at Niagara, restaurants, and hiking trails.
Pinnacle Of Luxury & Leisure -1 Bedroom With Washroom | Shared Full Kitchen - Pickering
Pickering
20/06 – 27/06
NZ$181/nighttotal: NZ$1267 (7 )

Pinnacle Of Luxury & Leisure -1 Bedroom With Washroom | Shared Full Kitchen

1 1
apartment , Oshawa
This newly constructed legal basement flat in Whitby is conveniently situated near Herber-Down Conservatory, Durham College, Ontario Tech University, and Lake Ontario, offering straightforward access to ski resorts and a spa.
This modern, open-plan studio apartment accommodates one guest and features a fully equipped shared kitchen, a queen bedroom with a spa shower, and complimentary high-speed Wi-Fi.
©2026 cozycozy.com