Book Holiday Homes in Pickering

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Featured Holiday Homes in Pickering

Luxury 2 Beds with Lakeview near CN Tower, Scotia Arena & FREE PRIVATE PARKING

Luxury 2 Beds with Lakeview near CN Tower, Scotia Arena & FREE PRIVATE PARKING

Toronto
Book a stay at this family-friendly vacation home in Toronto. Enjoy free WiFi, a fitness center, and a garden. Popular attractions CN Tower and Rogers Centre ...
Luxury 2 Beds with Lakeview near CN Tower, Scotia Arena & FREE PRIVATE PARKING
Spacious 3BR - Free Parking - City View - Pool - Gym

Spacious 3BR - Free Parking - City View - Pool - Gym

Toronto
Stay at this vacation home in Toronto. Enjoy free WiFi, a fitness center, and balconies. Popular attractions Scotiabank Arena and CN Tower are located ...
Spacious 3BR - Free Parking - City View - Pool - Gym
🌟 The Rouge Retreat: A Luxe Getaway in Markham 🍃✨

🌟 The Rouge Retreat: A Luxe Getaway in Markham 🍃✨

Markham
The price is NZ$663 per night from 6 Jan to 7 Jan
NZ$663
includes taxes & fees
6 Jan - 7 Jan 2025
Book a stay at this golf vacation home in Markham. Enjoy free WiFi and air conditioning. Popular attractions Toronto Zoo and Scarborough Town Centre are located ...
🌟 The Rouge Retreat: A Luxe Getaway in Markham 🍃✨
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Stunning Lake View Suite in Core Harbourfront

Stunning Lake View Suite in Core Harbourfront

Toronto
Stay at this vacation home in Toronto. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Scotiabank Arena and CN Tower are located ...
Stunning Lake View Suite in Core Harbourfront
The Isabella - Downtown Toronto

The Isabella - Downtown Toronto

Toronto
Stay at this vacation home in Toronto. Enjoy a fitness center, balconies, and an in-room coffeemaker. Popular attractions Scotiabank Arena and CN Tower are located ...
The Isabella - Downtown Toronto
Comfort Stay  - 2BR Suite - Free Parking - CN Tower View

Comfort Stay - 2BR Suite - Free Parking - CN Tower View

Toronto
Stay at this vacation home in Toronto. Enjoy a fitness center, balconies, and an in-room coffeemaker. Popular attractions Scotiabank Arena and CN Tower are located ...
Comfort Stay - 2BR Suite - Free Parking - CN Tower View
Restuary Stays - Pool|Gym|Sauna|Hot Tub|Free Parking

Restuary Stays - Pool|Gym|Sauna|Hot Tub|Free Parking

Toronto, ON
The price is NZ$556 per night from 24 Dec to 25 Dec
NZ$556
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in Toronto. Enjoy free WiFi, a fitness center, and balconies. Popular attractions Rogers Centre and CN Tower are located nearby.
Restuary Stays - Pool|Gym|Sauna|Hot Tub|Free Parking
Spectacular Presidential Loft - Downtown Toronto

Spectacular Presidential Loft - Downtown Toronto

Toronto
Stay at this vacation home in Toronto. Enjoy free WiFi, a fitness center, and an in-room coffeemaker. Popular attractions Rogers Centre and CN Tower are located ...
Spectacular Presidential Loft - Downtown Toronto
Amazing 1BR Suite - Rooftop Pool - View

Amazing 1BR Suite - Rooftop Pool - View

Toronto
Stay at this vacation home in Toronto. Enjoy free WiFi, a fitness center, and balconies. Popular attractions CN Tower and Rogers Centre are located nearby.
Amazing 1BR Suite - Rooftop Pool - View
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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.

Pickering Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Pickering vacation homes are the perfect way for you to wing it.

Holiday houses in Pickering let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Pickering in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Pickering adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pickering with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Pickering vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Pickering Holiday Homes essential information

Accommodation
828 Holiday Homes
Lowest Price
NZ$153
Highest Price
NZ$663
Popular accommodation
Luxury 2 Beds with Lakeview near CN Tower, Scotia Arena & FREE PRIVATE PARKING, Spacious 3BR - Free Parking - City View - Pool - Gym, 🌟 The Rouge Retreat: A Luxe Getaway in Markham 🍃✨ , Stunning Lake View Suite in Core Harbourfront, The Isabella - Downtown Toronto, Comfort Stay - 2BR Suite - Free Parking - CN Tower View, Restuary Stays - Pool|Gym|Sauna|Hot Tub|Free Parking, Spectacular Presidential Loft - Downtown Toronto, Amazing 1BR Suite - Rooftop Pool - View

Top trending hotels in Pickering

Pickering Casino Resort Hotel

Pickering Casino Resort Hotel

4 out of 5
888 Durham Live Ave, Pickering, ON
Fully refundableReserve now, pay when you stay
The price is NZ$153 per night from 24 Dec to 25 Dec
NZ$153
includes taxes & fees
24 Dec - 25 Dec
Stay at this 4-star business-friendly hotel in Pickering. Enjoy free WiFi, free parking, and 6 restaurants. Our guests praise the helpful staff and the clean ...
Pickering Casino Resort Hotel
Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is NZ$226 per night from 27 Dec to 28 Dec
NZ$226
includes taxes & fees
27 Dec - 28 Dec
Stay at this 4-star eco-certified hotel in Toronto. Enjoy free WiFi, 2 indoor pools, and 2 restaurants. Our guests praise the pool and the restaurant in our ...
Chelsea Hotel, Toronto
One King West Hotel & Residence

One King West Hotel & Residence

4 out of 5
1 King Street West, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is NZ$207 per night from 24 Dec to 25 Dec
NZ$207
includes taxes & fees
24 Dec - 25 Dec
Stay at this 4-star eco-certified aparthotel in Toronto. Enjoy free WiFi, room service, and a fitness center. Our guests praise the restaurant and the bar in ...
One King West Hotel & Residence
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Fairmont Royal York

Fairmont Royal York

4 out of 5
100 Front St West, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is NZ$317 per night from 24 Dec to 25 Dec
NZ$317
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this spa hotel in Toronto. Enjoy a full-service spa, 3 restaurants, and 3 bars/lounges. Our guests praise the pool and the restaurant in our reviews. ...
Fairmont Royal York
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.