A calm lake with rocky shores, surrounded by dense forest and a clear sky.

Pickering Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Pickering holiday rentals

A laundry area with stacked washers and dryers, wooden cabinets, and a tiled backsplash.

1. Modern Comforts, Quiet Neighborhood, Free 02 Parking

Modern Comforts, Quiet Neighborhood, Free 02 Parking
2.0 star property
Liverpool
10.0 out of 10, Exceptional, (1 review)
"House was neat and clean as showed in the pictures. We had a smooth check in process and enjoyed our stay. The house is really beautiful"
Canada
Prem
The price is AU$318
includes taxes & fees
12 Oct - 13 Oct
Modern Comforts, Quiet Neighborhood, Free 02 Parking
A living room with a sofa, coffee table, and patterned ottoman. There is a staircase with a railing and a door leading to another room.

2. Spacious Villa in Scarborough

Spacious Villa in Scarborough
2.0 star property
Scarborough
The price is AU$6,418
includes taxes & fees
12 Oct - 13 Oct
Spacious Villa in Scarborough
A hotel entrance with a glass facade and a sign reading "COSMOPOLITAN".

3. Executive Hotel Cosmopolitan and Spa

Executive Hotel Cosmopolitan and Spa
4.0 star property
Downtown Toronto
8.4 out of 10, Very good, (2,741 reviews)
"Love the location, check in was great. We had a lovely stay"
Canada
Teresa
The price is AU$254
includes taxes & fees
12 Oct - 13 Oct
Executive Hotel Cosmopolitan and Spa
A modern apartment with a balcony, a dining area, a living room with a sofa and ottoman, and a kitchen with a TV and fireplace.

4. Modern Apartments in North York

Modern Apartments in North York
4.0 star property
North York
8.2 out of 10, Very good, (397 reviews)
"Great place, and check in was pretty easy as they provided detailed instructions."
Canada
Shubeedsha
The price is AU$323
includes taxes & fees
13 Oct - 14 Oct
Modern Apartments in North York
A modern living space with a grey sofa, wooden flooring, a kitchen with red cabinets, and a dining area with white chairs.

5. Modern Downtown Suites Near CN Tower

Modern Downtown Suites Near CN Tower
3.5 star property
Downtown Toronto
9.2 out of 10, Wonderful, (11 reviews)
"Very spacious and location was great!"
Canada
Veronique-Anne
The price is AU$238
includes taxes & fees
12 Oct - 13 Oct
Modern Downtown Suites Near CN Tower
A rooftop terrace with outdoor seating and a city skyline view.

6. Nester Finn St. Lawrence Market

Nester Finn St. Lawrence Market
2.5 star property
Downtown Toronto
9.8 out of 10, Exceptional, (188 reviews)
"Enjoyed our stay"
United States
Hussam
The price is AU$309
includes taxes & fees
12 Oct - 13 Oct
Nester Finn St. Lawrence Market
A spacious lobby with a modern design, featuring a grey sectional sofa, a white sofa, and a wooden accent wall.

7. Modern Sonic Way Condos

Modern Sonic Way Condos
2.5 star property
North York
8.8 out of 10, Excellent, (23 reviews)
"Very clean, comfortable, and well located. We really enjoyed our stay."
Canada
Sophia
The price is AU$354
includes taxes & fees
13 Oct - 14 Oct
Modern Sonic Way Condos
A high-rise building with a modern glass facade, multiple floors, and a view of a cityscape at sunset.

8. Polaris Suites

Polaris Suites
4.0 star property
Downtown Toronto
9.2 out of 10, Wonderful, (887 reviews)
"Easy to check in, accommodating people, reasonable price."
Canada
Kerry
The price is AU$211
includes taxes & fees
12 Oct - 13 Oct
Polaris Suites
A modern kitchen with white cabinets and stainless steel appliances, a dining area with a glass table and chairs, and large windows offering a city view.

9. Maple Leaf Square

Maple Leaf Square
3.5 star property
Downtown Toronto
8.2 out of 10, Very good, (624 reviews)
"Great location"
Canada
Piotr
The price is AU$398
includes taxes & fees
12 Oct - 13 Oct
Maple Leaf Square
A dining area with a glass table and two chairs, a lamp, and a view of a cityscape through large windows.

10. Yonge Street Downtown Toronto Condos

Yonge Street Downtown Toronto Condos
4.0 star property
Downtown Toronto
8.8 out of 10, Excellent, (281 reviews)
"Great. Parking is a bit of a trick, but I figured it out."
United States
David
The price is AU$367
includes taxes & fees
12 Oct - 13 Oct
Yonge Street Downtown Toronto Condos
A high-rise building with a glass balcony, offering a city view.

11. Modern Downtown Apartments

Modern Downtown Apartments
4.0 star property
Downtown Toronto
8.0 out of 10, Very good, (628 reviews)
"Loved the location. What a beautiful place and close to everything"
Canada
Maria
The price is AU$433
includes taxes & fees
12 Oct - 13 Oct
Modern Downtown Apartments
A high-rise building with a modern architectural design, featuring a curved facade and multiple balconies.

12. Teahouse Condos in Downtown Toronto

Teahouse Condos in Downtown Toronto
4.0 star property
Downtown Toronto
8.4 out of 10, Very good, (84 reviews)
"Nice place"
United States
John-Rey
The price is AU$333
includes taxes & fees
12 Oct - 13 Oct
Teahouse Condos in Downtown Toronto
A modern outdoor seating area with a sofa and lounge chairs, a wooden deck, and a view of the ocean and a tower.

13. Skyline Suites - Next to MTCC, ACC & CN Tower

Skyline Suites - Next to MTCC, ACC & CN Tower
4.0 star property
Downtown Toronto
8.4 out of 10, Very good, (337 reviews)
"Loved the location!! Great place to stay while visiting Toronto."
Canada
Cyrene
The price is AU$271
includes taxes & fees
9 Nov - 10 Nov
Skyline Suites - Next to MTCC, ACC & CN Tower
A living room with a sofa, armchair, wooden cabinet, and a small table with a bowl.

14. 1 bd Apartment Sleeps 4- 20 Mins From Everything!

1 bd Apartment Sleeps 4- 20 Mins From Everything!
2.0 star property
North York
The price is AU$383
includes taxes & fees
12 Oct - 13 Oct
1 bd Apartment Sleeps 4- 20 Mins From Everything!
A hotel room with a large bed, a bedside table with a lamp, a mirror, and a wooden floor.

15. StayToronto - Eaton Centre Escape

StayToronto - Eaton Centre Escape
3.0 star property
Downtown Toronto
8.0 out of 10, Very good, (1 review)
"Thanks!"
Canada
Layne
The price is AU$219
includes taxes & fees
12 Oct - 13 Oct
StayToronto - Eaton Centre Escape
A dining area with a wooden table, four chairs, a vase with flowers, and a television in the background.

16. Dan Leckie Apartments

Dan Leckie Apartments
3.0 star property
Downtown Toronto
9.8 out of 10, Exceptional, (6 reviews)
"loved the location. central and CLEANNNNNNN"
United States
Jayne
The price is AU$155
includes taxes & fees
15 Oct - 16 Oct
Dan Leckie Apartments
Room

17. Chic Suites in Downtown Toronto

Chic Suites in Downtown Toronto
3.5 star property
Downtown Toronto
10.0 out of 10, Exceptional, (1 review)
"The place looks exactly like the pictures—actually, even better in person! We loved the balcony and the beautiful city lights at night. The location was perfect for us, the check-in instructions were very easy to follow, and the host/support team replied right away whenever we had questions. We had a great stay and would definitely recommend it!"
Canada
Ernesto Luis
The price is AU$307
includes taxes & fees
9 Nov - 10 Nov
Chic Suites in Downtown Toronto
A high-rise apartment with a city view, a green sofa, a glass coffee table, and a modern chandelier.

18. Bellair Yorkville

Bellair Yorkville
3.5 star property
Old Toronto
9.6 out of 10, Exceptional, (110 reviews)
"The location is perfect right in the heart of Yorkville the only problem was the amenities, such as towels and soap etc. inside the unit which were in short supply and some minor maintenance related issues that could be attended to"
Canada
joel
The price is AU$531
includes taxes & fees
1 Nov - 2 Nov
Bellair Yorkville
A modern living room with a grey sofa, yellow cushions, a glass coffee table, and a view of tall buildings through large windows.

19. Modern Lillian Street Condos Midtown Toronto

Modern Lillian Street Condos Midtown Toronto
4.0 star property
Old Toronto
8.4 out of 10, Very good, (334 reviews)
"good location, good staff"
Canada
nathalia
The price is AU$343
includes taxes & fees
18 Oct - 19 Oct
Modern Lillian Street Condos Midtown Toronto
A hotel room with two beds, each with white linens and towels, a wooden headboard, bedside lamps, and a nightstand with a phone and clock.

20. HarbourtFront Center

HarbourtFront Center
2.5 star property
Downtown Toronto
8.0 out of 10, Very good, (4 reviews)
"Perfect for staying"
Canada
Lovejoban
The price is AU$390
includes taxes & fees
17 Oct - 18 Oct
HarbourtFront Center
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pickering Hotel Reviews

Fairmont Royal York

Fairmont Royal York

10/10 Excellent
"Clean and helpful staff"
Purisima 2-night trip
Posted 1 hour ago
Fairmont Royal York

Find out more about Pickering

Everything you need to know about Pickering holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pickering holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pickering holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pickering holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pickering. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pickering holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pickering holiday rentals we have selected for you start as low as AU$211 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pickering rentals

At Expedia, we put the best Pickering holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pickering rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pickering holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pickering. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Pickering?

Yes, there are holiday rentals in Pickering close to Chestnut Hill Developments Recreation Complex, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Pickering is known for its zoo. Make sure you have time to check out the hockey games and coffee shops during your trip.

What are some of the best holiday rentals that Pickering has to offer?

Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!: This highly rated holiday home rental in Pickering is located near the beach, and offers a garden, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

How many holiday rentals are there in Pickering?

Choose from 72 Expedia holiday rentals in Pickering for a memorable holiday.

What can I see and do in Pickering?

Rouge National Urban Park and Lake Ontario are a couple of scenic spots to enjoy the outdoors, whereas Luke Andrews Wood Sculptures is one of the cultural attractions. Pickering Casino Resort and Deer Creek North Golf Course are other places to visit while you're in town.

What are holiday rentals like in Pickering?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pickering. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip.