Vacation rentals in Pickering

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Top-rated vacation rentals in Pickering

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest suite in Pickering
Separate 2 Bedroom & 2 Washroom up to 4 people.
Hotel-style apartment in a home annex. Not a basement. The apartment has 2 bedrooms with attached washrooms, Living area, kitchen, dining. Our property accommodates up to 4 people. Children are welcome to stay. Conveniently located just off Highway 401. Close to downtown Pickering, Go Station, mall, restaurants. We are a good stopover point if you are traveling to downtown Toronto which is only a 40 min drive. Note: Show us your ID when "Checking In" and it has to match with your booking name.
May 21 – 28
$168 CAD per night
4.93 out of 5 average rating, 123 reviews
Guest favourite
Dome in Bradford West Gwillimbury
Four season glamping dome under the stars
Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...
Nov. 28 – Dec. 5
$184 CAD per night
4.98 out of 5 average rating, 198 reviews
Guest favourite
Apartment in Whitby
Serenity Suite w/Sauna-Your Entire Apt Awaits You
LONG-TERM stays welcome. A short drive to Thermea Spa Village. This is a beautiful, newly renovated, spacious basement apartment, perfect for two. Located in Whitby Shores (w/ hot tub) just a few minutes’ walk to Lake Ontario, a park, & trails, the house is situated in a quiet and friendly neighbourhood. It is close to all amenities - shopping, movie theatre, and other entertainment options, restaurants, GO Train station, Hwy 401, and easy access to Hwy 407. We look forward to meeting you!
Oct. 29 – Nov. 5
$124 CAD per night
4.94 out of 5 average rating, 144 reviews

Popular amenities for Pickering vacation rentals

Stay near Pickering's top sights

Pickering Town Centre45 locals recommend
Toronto Pan Am Sports Centre26 locals recommend
Ajax Waterfront Park17 locals recommend
Costco Wholesale7 locals recommend
Beachfront Park8 locals recommend
Port Union Waterfront Park10 locals recommend

Other great vacation rentals in Pickering

Guest favourite
Home in Pickering
Cosy 3-Bedroom Home in Quiet Cul-de-Sac.
Jan. 30 – Feb. 6
$207 CAD per night
4.8 out of 5 average rating, 54 reviews
Guest favourite
Bungalow in Pickering
Beachy bungalow
Apr. 21 – 28
$198 CAD per night
5.0 out of 5 average rating, 20 reviews
Guest favourite
Guesthouse in Pickering
Luxury Ground-Level "Suite Escape"
Dec. 8 – 15
$174 CAD per night
4.95 out of 5 average rating, 20 reviews
Guest favourite
Guest suite in Pickering
*Hotub* Walkout Patio* Separate Unit* Inlaw Suite!
May 21 – 28
$130 CAD per night
4.89 out of 5 average rating, 100 reviews
Guest favourite
Apartment in Pickering
Pure Springs Oasis
Jul. 13 – 20
$177 CAD per night
4.82 out of 5 average rating, 17 reviews
Guest favourite
Home in Ajax
Ultra-Modern Luxury Retreat! Close to Thermea SPA.
Jul. 23 – 30
$206 CAD per night
5.0 out of 5 average rating, 61 reviews
Guest favourite
Apartment in Ajax
Luxurious Private Suite by the Lake
Sep. 20 – 27
$106 CAD per night
4.83 out of 5 average rating, 81 reviews
Guest favourite
Guest suite in Pickering
Guest Suite in Pickering
Feb. 4 – 11
$223 CAD per night
4.93 out of 5 average rating, 61 reviews
Guest favourite
Apartment in Pickering
Rouge Valley National Park
Apr. 27 – May 4
$112 CAD per night
4.91 out of 5 average rating, 32 reviews
Guest favourite
Townhouse in Pickering
Gorgeous 2-BR Townhouse with full stocked kitchen
Aug. 5 – 12
$189 CAD per night
4.95 out of 5 average rating, 74 reviews
Guest favourite
Guesthouse in Pickering
Spacious fully private studio basement & parking
Dec. 8 – 15
$104 CAD per night
4.93 out of 5 average rating, 14 reviews
Guest favourite
Guest suite in Ajax
1 bed, 1 bath beside Golf Course
Oct. 13 – 20
$123 CAD per night
4.96 out of 5 average rating, 28 reviews

Quick stats about vacation rentals in Pickering

Total rentals

1.4K properties

Rentals with dedicated workspaces

840 properties have a dedicated workspace

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

220 properties allow pets

Family-friendly rentals

540 properties are a good fit for families

Total number of reviews

26K reviews

Destinations to explore