Book Holiday Homes in Pickering

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Featured Holiday Homes in Pickering

Entire Spacious 5BR Home  6 Beds, 3.5BA, Wi-Fi, 6 TVs, Parking & BBQ

Entire Spacious 5BR Home 6 Beds, 3.5BA, Wi-Fi, 6 TVs, Parking & BBQ

Richmond Hill, ON ON
Stay at this holiday home in Richmond Hill. Enjoy laundry facilities, in-room fireplaces and air conditioning. Popular attractions Vaughan Mills Mall and Elvis ...
Opens in a new windowEntire Spacious 5BR Home 6 Beds, 3.5BA, Wi-Fi, 6 TVs, Parking & BBQ
Eve’s Luxury Get Away

Eve’s Luxury Get Away

Whitby ON
The price is NZ$484 per night from 12 Jan to 13 Jan
NZ$484
12 Jan - 13 Jan 2026
includes taxes & fees
Stay at this holiday home in Whitby. Enjoy laundry facilities. Popular attractions Whitby History Museum & Children's Centre and Deer Creek North Golf Course ...
Opens in a new windowEve’s Luxury Get Away
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
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GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking

GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking

Ajax ON
The price is NZ$235 per night from 29 Dec to 30 Dec
NZ$235
29 Dec - 30 Dec
includes taxes & fees
Stay at this holiday home in Ajax. Enjoy air conditioning. Popular attractions Pickering Casino Resort and Veterans' Point Gardens are located nearby.
Opens in a new windowGORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking
Fabulous 3 bedroom in Whitby

Fabulous 3 bedroom in Whitby

Whitby ON
The price is NZ$349 per night from 31 Dec to 1 Jan
NZ$349
31 Dec - 1 Jan 2026
includes taxes & fees
Stay at this holiday home in Whitby. Enjoy a garden, patios and cable/satellite TV service. Popular attractions Whitby History Museum & Children's Centre and ...
Opens in a new windowFabulous 3 bedroom in Whitby
Newly renovated 2-story house with 5 bed rooms and 4 washrooms

Newly renovated 2-story house with 5 bed rooms and 4 washrooms

Richmond Hill ON
Stay at this golf holiday home in Richmond Hill. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Summit Golf & Country Club and Richmond ...
Opens in a new windowNewly renovated 2-story house with 5 bed rooms and 4 washrooms
Woodspring Vacation Home

Woodspring Vacation Home

Newmarket ON
The price is NZ$691 per night from 26 Dec to 27 Dec
NZ$691
26 Dec - 27 Dec
includes taxes & fees
Stay at this holiday home in Newmarket. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Upper Canada Mall and SilverCity ...
Opens in a new windowWoodspring Vacation Home
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.
Dazzling Home Next to Beach & Go Station

Dazzling Home Next to Beach & Go Station

3.5 out of 5
736 Hillview Crescent Pickering ON
Stay at this holiday home in Pickering. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Toronto Zoo and Millennium Square are located ...
Opens in a new windowDazzling Home Next to Beach & Go Station
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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$179
Highest Price
NZ$691
Popular accommodation
Entire Spacious 5BR Home 6 Beds, 3.5BA, Wi-Fi, 6 TVs, Parking & BBQ, Eve’s Luxury Get Away, Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything, GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking, Fabulous 3 bedroom in Whitby , Newly renovated 2-story house with 5 bed rooms and 4 washrooms, Woodspring Vacation Home, Newly renovated 2 bedroom suite lower level., Dazzling Home Next to Beach & Go Station

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$179 per night from 4 Jan to 5 Jan
NZ$179
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Pickering. Enjoy free Wi-Fi, free parking and 6 restaurants. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowPickering 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$257 per night from 22 Jan to 23 Jan
NZ$257
22 Jan - 23 Jan 2026
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
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$215 per night from 1 Jan to 2 Jan
NZ$215
1 Jan - 2 Jan 2026
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
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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$398 per night from 28 Dec to 29 Dec
NZ$398
28 Dec - 29 Dec
includes taxes & fees
Stay at this luxury hotel in Toronto. Enjoy 3 restaurants, 3 bars/lounges and breakfast (surcharge). Our guests praise the pool and the restaurant in their reviews. ...
Opens in a new windowFairmont 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.

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^Subject to availability and chosen travel dates.