Book Holiday Homes in Pickering

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Featured Holiday Homes in Pickering

Upscale & Bright 6 Bedroom 2.5 Bathroom House

Upscale & Bright 6 Bedroom 2.5 Bathroom House

Richmond Hill ON
The price is NZ$776 per night from 8 Apr to 9 Apr
NZ$776
8 Apr - 9 Apr
includes taxes & fees
Stay at this holiday home in Richmond Hill. Enjoy laundry facilities and air conditioning. Popular attractions Canada's Wonderland and Vaughan Mills Mall are ...
Opens in a new windowUpscale & Bright 6 Bedroom 2.5 Bathroom House
The Artist House in Downtown Richmond Hill [2bdrm|1 bath]

The Artist House in Downtown Richmond Hill [2bdrm|1 bath]

Richmond Hill ON
Stay at this holiday home in Richmond Hill. Enjoy free Wi-Fi, Netflix and an in-room coffee maker. Popular attractions Canada's Wonderland and Vaughan Mills ...
Opens in a new windowThe Artist House in Downtown Richmond Hill [2bdrm|1 bath]
Newly renovated 3 bedroom unit Richmond Hill

Newly renovated 3 bedroom unit Richmond Hill

Richmond Hill ON
Stay at this holiday home in Richmond Hill. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Richmond Hill Heritage Centre and Richmond ...
Opens in a new windowNewly renovated 3 bedroom unit Richmond Hill
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Family frieindly house in richmond hill 7beds

Family frieindly house in richmond hill 7beds

Richmond Hill ON
Stay at this holiday home in Richmond Hill. Enjoy laundry facilities and air conditioning. Popular attractions Richmond Hill Heritage Centre and Richmond Hill ...
Opens in a new windowFamily frieindly house in richmond hill 7beds
Newly renovated 2 bedroom suite lower level.

Newly renovated 2 bedroom suite lower level.

Richmond Hill ON
Stay at this holiday home in Richmond Hill. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Richmond Hill Heritage Centre ...
Opens in a new windowNewly renovated 2 bedroom suite lower level.
Luxury 5 Bedroom Home in Richmond Hill, Free Parking, Private Gym

Luxury 5 Bedroom Home in Richmond Hill, Free Parking, Private Gym

Richmond Hill ON
Stay at this holiday home in Richmond Hill. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Lake Wilcox Park and Richmond Hill Centre for ...
Opens in a new windowLuxury 5 Bedroom Home in Richmond Hill, Free Parking, Private Gym
5 Bedroom Resort Vibes| Hot Tub + Dry Sauna + Chill Zone | BIG FAMILY HOME

5 Bedroom Resort Vibes| Hot Tub + Dry Sauna + Chill Zone | BIG FAMILY HOME

Richmond Hill ON
Stay at this family-friendly holiday home in Richmond Hill. Enjoy free Wi-Fi, a sauna and a garden. Popular attractions Canada's Wonderland and Vaughan Mills ...
Opens in a new window5 Bedroom Resort Vibes| Hot Tub + Dry Sauna + Chill Zone | BIG FAMILY HOME
Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything

Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything

Ajax ON
Stay at this holiday home in Ajax. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Pickering Casino Resort and Veterans' Point Gardens ...
Opens in a new windowBrand New Luxury Entire Private Suite, Open Concept Retreat, close to everything
Charming Townhouse Retreat Near Nordic Spa

Charming Townhouse Retreat Near Nordic Spa

Whitby ON
Stay at this golf holiday home in Whitby. Enjoy laundry facilities, balconies and an in-room coffee maker. Popular attractions Ontario Regiment Museum and Whitby ...
Opens in a new windowCharming Townhouse Retreat Near Nordic Spa
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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
917 Holiday Homes
Lowest Price
NZ$260
Highest Price
NZ$776
Popular accommodation
Upscale & Bright 6 Bedroom 2.5 Bathroom House, The Artist House in Downtown Richmond Hill [2bdrm|1 bath], Newly renovated 3 bedroom unit Richmond Hill, Family frieindly house in richmond hill 7beds, Newly renovated 2 bedroom suite lower level., Luxury 5 Bedroom Home in Richmond Hill, Free Parking, Private Gym, 5 Bedroom Resort Vibes| Hot Tub + Dry Sauna + Chill Zone | BIG FAMILY HOME, Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything, Charming Townhouse Retreat Near Nordic Spa

Top trending hotels in Pickering

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
30 Widmer St Toronto ON
Fully refundableReserve now, pay when you stay
The price is NZ$363 per night from 2 Apr to 3 Apr
NZ$363
2 Apr - 3 Apr
includes taxes & fees
Stay at this business-friendly hotel in Toronto. Enjoy free breakfast, free Wi-Fi and a 24-hour fitness centre. Popular attractions CN Tower and Rogers Centre ...
Opens in a new windowHotel Riu Plaza Toronto
Holiday Inn Toronto Downtown Centre by IHG

Holiday Inn Toronto Downtown Centre by IHG

3.5 out of 5
30 Carlton Street Toronto ON
Fully refundable
The price is NZ$306 per night from 2 Apr to 3 Apr
NZ$306
2 Apr - 3 Apr
includes taxes & fees
Stay at this business-friendly hotel in Toronto. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the restaurant and the helpful ...
Opens in a new windowHoliday Inn Toronto Downtown Centre by IHG
DoubleTree by Hilton Hotel Toronto Downtown

DoubleTree by Hilton Hotel Toronto Downtown

4 out of 5
108 Chestnut St Toronto ON
Fully refundableReserve now, pay when you stay
The price is NZ$294 per night from 2 Apr to 3 Apr
NZ$294
2 Apr - 3 Apr
includes taxes & fees
Stay at this business-friendly hotel in Toronto. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the breakfast and the restaurant ...
Opens in a new windowDoubleTree by Hilton Hotel Toronto Downtown
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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$260 per night from 2 Apr to 3 Apr
NZ$260
2 Apr - 3 Apr
includes taxes & fees
Stay at this family-friendly hotel in Toronto. Enjoy free Wi-Fi, 2 indoor pools and 2 restaurants. Our guests praise the pool and the restaurant in their reviews. ...
Opens in a new windowChelsea Hotel, Toronto
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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.