
Holiday rentals in Pickering
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Top-rated holiday rentals in Pickering
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“Elysium” Where happiness is real!
Stay connected with our fast Bell Fibe Wi-Fi, free parking and unwind with over 1000 streaming channels on our TV, including Netflix and Prime. Whether you're here to catch the game or watch an exciting fight you’ll have everything you need for a great time Our location is the perfect base for discovering all that Pickering has to offer. You’ll be just a short drive away from fantastic restaurants, lively bars, shopping spots, and even casinos—everything you need for a fun and convenient stay!

Brand New Private Luxury Suite Open Consept living
Sun filled Private Suite, cozy & modern. Entire space with separate entrance. Peaceful Ravine, walking path & Sunrise. Minutes to the 401 & Ajax Go Station. 18 min to Toronto Pan Am Sports Centre. 30 min to downtown Toronto. Walking distance to a wide variety of restaurants, major shopping plazas, Walmart, Costco, RCSS, Iqbal foods, Ajax Downs & Casino. Life Time Athletic, Ajax convention Centre. Minutes to Lake Ontario & Pickering Casino. 12 min to Dagmar Ski Resort & Whitby Thermëa spa village

* HOT TUB* Guest Suite - Minutes to the Beach!
Welcome to the Hidden Gem - Romanic Zen Den! Your separate entrance will lead you to your lower level of the bungalow and is the perfect place to find your inner zen after enjoying the beautiful outdoors of Pickering. Elevate your experience with add-on packages! *there is another guest unit on the main floor. You will hear signs of life from above *9 pm pls no loud noise outside 4 min walk to Beach 12 min Casino 11 min Zoo 7 min Mall/Movies 18 min Thermea Spa 30 min Dwntwn Toronto

Guest Suite in Pickering
Enjoy in the comfort of this modern 3 bedrooms, 2 bathrooms lower unit suite with separate entrance and outstanding facilities in the peaceful family-friendly neighborhood of Pickering, at the border of Toronto. Enjoy free access to high speed Wi-Fi, TV, Arcade, fully functional kitchen, laundry, and work desks in two of the rooms. We trust that you will have an amazing time! Conveniently located close to Shopping, Dining, Pickering Casino, Hwy 401, and a 30-mins drive to downtown Toronto.

Bright Private Suite w/Separate Entrance & Patio
PRIVATE Walk Out Basement Apartment W/Separate Entrance. 420 Sq.Ft space. Queen Sized Bed. Oversized Shower w/ Rainfall Shower-head. Microwave, Two Mini Fridges, Coffee/Hot Water Tea Maker. Please note: not a full kitchen. Dining/Work Table w/Benches. High Speed Wi-fi. Living Room w/ Reclining Lazy Boy Couch and 50” Smart Tv. Over 1000 Live Tv Channels and Netflix. Private Little Backyard Patio w/Table. Private Driveway ( 2 Cars). 1 Min Drive to Hwy 401. 15 Min Walk to Ajax Go Station.

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.
Welcome! Our 3 bedroom, 2 bath home is centrally located on a low traffic court. Spacious, clean and bright! Featuring a large walk-out family room with high ceilings and a wood-burning fireplace. Completely renovated with wood floors throughout. Large sunny west-facing backyard and 6 car-park on the driveway. Enjoy many unique amenities like our chromo-therapy steam room & outdoor Brazilian hammock. Walking distance to strip plaza, restaurants & parks. A comfortable home away from home!

Private Loft w Sauna, Fireplace, Wi-Fi & Projector
Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE in 2021, this private loft includes a sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

Lakeside Sweet Home
Private entrance with passcode keypad self check-in 10-MINUTES WALK to BEACH !!! 2 bedrooms, Queen-sized+Full-sized bed and a Sofa bed in the living room 30-sec walk to Bus stop 4-min drive to Pickering Go station 3-min drive to reach Hwy 401 8-min drive Toronto Zoo 30-min drive Toronto City Center 40-inch TV with smart TV box Free Washer and Dryer in the suite Fully equipped Kitchen. Coffee maker,stove,oven,microwave, and refrigerator, toaster, cookware and dishes

Lower Unit - Central location
Enjoy the charming touches of this cozy basement suite with a clean modern feel. Beautifully decorated featuring a spacious open concept living room/kitchen combo area with spacious island and a brightly lit bathroom with a stand-up shower. This guest suite with your very own private entrance is bright and full of warmth. Conveniently located: 5 min walk to Pickering Town Center, 10 min walk to the Pickering GO and 2 min drive to 401.

Ultra-Modern Luxury Retreat! Close to Thermea SPA.
COZY and INVITING, this modern suite is in a quiet, family-friendly Ajax neighborhood. Just 10 minutes to Thermea Spa and Ajax GO Station, and a short walk to parks, shops, and groceries. Newly built with deluxe finishes, the 1,000 sq. ft. space includes in-floor heating, an electric fireplace, a spacious sofa, and smart TV with Netflix/Prime. Downtown Toronto is 35–45 mins by car, and Pearson Airport or Mississauga in about 55 mins.

Muskoka on the City
Located in Rouge National Urban Park, steps from a beautiful lake and beach. Enjoy hiking, kayaking, biking, and fishing nearby. Close to Toronto Zoo, Seaton Trail, highways, restaurants, shopping malls, and Rouge Hill GO Station. Bright ground-level suite with a private entrance, kitchen, dining area, TV, bathroom, and queen bedroom. Includes Wi-Fi and laundry. Perfect for a peaceful and convenient stay!

Luxurious, modern basement unit
Kick back and relax in this calm, stylish space. Prime location near bus stop, shops, restaurants there is something for everyone. Whether you are here for work or pleasure this is your best place. Your home away home. Nice and modern new basement apartment with fast and reliable fibe internet , smart TV with Netflix, Amazon prime and Disney plus , dedicated work space and free parking
Popular amenities for Pickering holiday rentals
Other great holiday rentals in Pickering

King Studio Suit W/parking+1st flr wlkout

Modern Basement Apartment

Home away home

Beautiful Private Guest House

Tranquil Haven: Luxurious 2BR Retreat Near Hwy 401

Luxury Suite w/ Cafe & Sauna in Pickering

Miden Touch: Stylish Modern Basement w/ Workspace

Ravine Retreat | Chef Kitchen | Toronto Zoo | SPA
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $81 SGD | $82 SGD | $83 SGD | $86 SGD | $92 SGD | $95 SGD | $99 SGD | $102 SGD | $94 SGD | $95 SGD | $92 SGD | $89 SGD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Frequently Asked Questions
How much does it cost to stay in house rentals in Pickering?
Experience the best of Pickering with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do guesthouse rentals in Pickering have wifi?
Absolutely! We offer over 10 guesthouse rentals with wifi in Pickering. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Pickering have a kitchen?
Absolutely! We offer over 70 townhouse rentals with a kitchen in Pickering. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Private Suite Rentals in Pickering?
Enhance your stay in our Private Suite Rentals with the most popular amenities: over 150 homes with air conditioning, over 130 homes with a kitchen, over 140 homes with free parking, over 160 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Pickering?
Yes! Work meets play with ease at over 940 vacation rentals in Pickering featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do guesthouse rentals in Pickering have air conditioning?
Absolutely! We offer over 10 guesthouse rentals with air conditioning in Pickering. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Pickering?
Pickering has more than 620 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there Pickering vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Pickering, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Pickering?
Make yourself at home in Pickering by choosing from our most frequently booked neighborhoods. We have over 10 vacation rentals in Brooklin, over 1,590 vacation rentals in Guildwood, and over 1,400 vacation rentals in Malvern.
Do house rentals in Pickering have free parking?
Absolutely! We offer over 880 house rentals with free parking in Pickering. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Pickering

Total holiday rentals
Explore 1,540 holiday rentals in Pickering

Nightly prices starting at
Pickering holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 40,310 verified reviews to help you choose

Family-friendly holiday rentals
620 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 270 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
940 properties have a dedicated workspace

Wifi availability
1,510 of Pickering holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pickering rentals

4.7 Average rating
Pickering stays receive an average rating of 4.7 out of 5 from guests
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Distillery District
- Metro Toronto Convention Centre
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- Financial District
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- BMO Field
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Rouge National Urban Park
- Royal Ontario Museum
- Christie Pits Park
- Toronto City Hall
- Royal Woodbine Golf Club
- Jackson-Triggs Niagara Estate




