Compare Pickering Villas

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Featured Villas in Pickering

Richmond Hill 5BR | Game Room | Huge Yard | 3 Parking , Pets OK

Richmond Hill 5BR | Game Room | Huge Yard | 3 Parking , Pets OK

Richmond Hill ON
$249 nightly
The price is $282 total per night
$282 total
Jul 14 - Jul 15
Total with taxes and fees
At this villa, guests have access to an arcade/game room, laundry facilities, and a garden. This family-friendly villa also has barbecue grills.
Kitchen
Washer
Modern Gem| 2026 FIFA - 40 Mins to BMO Field | THH

Modern Gem| 2026 FIFA - 40 Mins to BMO Field | THH

Ajax ON
$273 nightly
The price is $309 total per night
$309 total
Jul 12 - Jul 13
Total with taxes and fees
At this villa, guests have access to features like laundry facilities.
Kitchen
Washer
Forest Villa for Large Group with Outdoor Pool and indoor Swim Spa-Pet friendly

Forest Villa for Large Group with Outdoor Pool and indoor Swim Spa-Pet friendly

Newmarket ON
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Other amenities at this golf villa include a garden and barbecue grills.
Pool
Hot Tub
Cheerful luxury 7 bedroom/7 washroom ravine house

Cheerful luxury 7 bedroom/7 washroom ravine house

Richmond Hill ON
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has barbecue grills.
Kitchen
Washer
Elegant & Cozy English Villa with beautiful fenced backyard

Elegant & Cozy English Villa with beautiful fenced backyard

Kettleby ON
At this villa, guests have access to a gym, laundry facilities, and a garden. This family-friendly villa also has barbecue grills.
Kitchen
Washer
Grand Waterfront Retreat – Under 1hr from Toronto

Grand Waterfront Retreat – Under 1hr from Toronto

Bowmanville ON
$398 nightly
The price is $450 total per night
$450 total
Jul 16 - Jul 17
Total with taxes and fees
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has barbecue grills.
Kitchen
Washer
Ajax Heaven

Ajax Heaven

2 out of 5
Southam St Ajax ON
Free parking is included with your stay.
Parking included
Free WiFi
Luxury 4 Bedroom/5 Bathroom Huge Ravine Backyard

Luxury 4 Bedroom/5 Bathroom Huge Ravine Backyard

Richmond Hill ON
Guests of this villa enjoy access to ski-in/ski-out access, laundry facilities, and barbecue grills. This ski villa also has a garden.
Kitchen
Washer
King City Villa • 4 Bedroom Retreat with Spacious Backyard

King City Villa • 4 Bedroom Retreat with Spacious Backyard

King City ON
At this villa, guests have access to features like laundry facilities.
Washer
Dryer
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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.

Hotel Options in Pickering

    Pickering Casino Resort Hotel

    Pickering Casino Resort Hotel

    888 Durham Live Ave Pickering ON
    $96 nightly
    The price is $112 total per night from Jul 16 to Jul 17
    $112 total
    Jul 16 - Jul 17
    Total with taxes and fees
    9/10 Wonderful! (4,905 reviews)
    Chelsea Hotel, Toronto

    Chelsea Hotel, Toronto

    33 Gerrard St W Toronto ON
    $143 nightly
    The price is $176 total per night from Jul 12 to Jul 13
    $176 total
    Jul 12 - Jul 13
    Total with taxes and fees
    9/10 Wonderful! (477 reviews)
    Holiday Inn Toronto Downtown Centre by IHG

    Holiday Inn Toronto Downtown Centre by IHG

    30 Carlton Street Toronto ON
    $122 nightly
    The price is $149 total per night from Jul 26 to Jul 27
    $149 total
    Jul 26 - Jul 27
    Total with taxes and fees
    8.6/10 Excellent! (6,120 reviews)

Luxury Villas

Book luxury villas in Pickering
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Pickering. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Pickering, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Pickering
You won’t have a problem finding your own space in Pickering. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Pickering on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Pickering rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Pickering Villas essential information

Accommodation
12 Villas
Lowest Price
$112
Highest Price
$450
Popular accommodation
Richmond Hill 5BR | Game Room | Huge Yard | 3 Parking , Pets OK, Modern Gem| 2026 FIFA - 40 Mins to BMO Field | THH, Forest Villa for Large Group with Outdoor Pool and indoor Swim Spa-Pet friendly, Cheerful luxury 7 bedroom/7 washroom ravine house, Elegant & Cozy English Villa with beautiful fenced backyard, Grand Waterfront Retreat – Under 1hr from Toronto, Ajax Heaven, Luxury 4 Bedroom/5 Bathroom Huge Ravine Backyard, King City Villa • 4 Bedroom Retreat with Spacious Backyard