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Holiday rentals in Pickering

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Top-rated holiday rentals in Pickering

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Top guest favourite
A modern kitchenette is shown, featuring a silver refrigerator and a stainless-steel microwave above the stove. Light cabinetry contrasts with a wood countertop. A gray sofa sits in the foreground, accompanied by a wall clock and a lamp, enhancing the sleek and organized space.
Apartment in Pickering
4.93 out of 5 average rating, 335 reviews

“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!

Top guest favourite
A contemporary living area is shown, featuring a plush green sofa and a round wooden coffee table. A flat-screen TV is mounted on the wall, with a modern lamp and a potted plant adding character to the space. Soft lighting creates a relaxed ambiance.
Flat in Ajax
4.98 out of 5 average rating, 66 reviews

Miden Touch: Stylish Modern Basement w/ Workspace

Escape to our modern basement suite in Ajax, perfectly situated just 10 minutes' drive from Ajax Waterfront and close to the 401. This newly renovated space combines style, comfort, and convenience for an unforgettable stay. Enjoy a private entrance leading to a large bedroom with a plush queen bed and a stylish bathroom stocked with essentials. Relax in the contemporary living area, featuring a comfy sofa and smart TV with full kitchen, Wi-Fi, dedicated workspace and laundry facilities in unit.

Top guest favourite
The spacious living area features a leather sectional sofa and a cozy ottoman, situated atop a soft area rug. A modern kitchen with an island and dark cabinetry is visible in the background, complemented by ambient blue lighting.
Guest suite in Ajax
4.99 out of 5 average rating, 145 reviews

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

Guest favourite
A cozy living area features a brick fireplace with a warm flame, complemented by soft lighting from decorative lanterns. A coffee table is adorned with candles and a chilled bottle of champagne, while comfortable seating invites relaxation.
Guest suite in Pickering
4.87 out of 5 average rating, 732 reviews

* 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

Top guest favourite
A cozy living area is presented, featuring a large comfortable couch and a wooden coffee table. A television stands atop a media console, with a decorative plant placed on the table. The space is illuminated by natural light streaming through glass doors, leading to the outdoor patio.
Guest suite in Ajax
4.96 out of 5 average rating, 529 reviews

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.

Guest favourite
A warm living area features a large leather sofa paired with a circular chair. A rustic wooden coffee table is positioned in front. Natural light filters through sheer curtains, illuminating the space with a cozy ambiance. A wood-burning fireplace is framed by vertical wood paneling.
Home in Pickering
4.84 out of 5 average rating, 113 reviews

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!

Guest favourite
A bright living area features a neutral-toned sofa positioned across from a wooden coffee table adorned with a small vase of colorful flowers. A wall art piece of abstract design adds visual interest. The open layout includes doorways leading to the kitchen and bedrooms.
Home in Pickering
4.86 out of 5 average rating, 148 reviews

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

Guest favourite
Guest suite in Pickering
4.91 out of 5 average rating, 257 reviews

Urban HotTub Oasis/Separate Entrance/Unit/DT 30min

Completely private studio suite kitchenette (no full kitchen) Exclusive hot tub access for ultimate relaxation Modern space with Fireplace and smart TV for streaming Fast Wi-Fi and dedicated parking included Approximately 30 minutes from downtown Toronto Conveniently located near Thermea Spa and Frenchman’s Bay, Pickering Casino Resort & Toronto Zoo One parking spot for SUV size car. Safe and secure with a disclosed entrance camera and responsive hosting

Top guest favourite
A cozy bedroom features a spacious bed with elegant bedding, flanked by two nightstands. A dresser is positioned against the wall, and natural light filters through a window, illuminating the soft grey walls and light-colored flooring.
Home in Ajax
4.98 out of 5 average rating, 80 reviews

Private Sauna Suite Retreat

1 Bedroom • 1.5 Bathrooms • Private Entire Unit Newly renovated and quiet, just minutes from Hwy 401 and local restaurants. Highlights • Private self check-in • Driveway parking for 1 car • Private sauna • 55 Inch TV with Netflix Amenities Fresh towels, linens, tooth brushes & pastes, hairdryer, home essentials, shower essentials, and extra pillows/towels on request. Spotless home, quick replies, and your comfort guaranteed - book with confidence.

Top guest favourite
The living area features a spacious couch and two cozy blue accent chairs, positioned around a round coffee table. A large flat-screen TV is mounted on the wall, while a modern mirror reflects the open concept layout, enhancing the light from the recessed lighting.
Home in Ajax
5 out of 5 average rating, 121 reviews

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.

Superhost
A serene landscape of golden grasses and vibrant trees reflects in calm water. The scene captures a natural environment, inviting contemplation and enjoyment of the surrounding flora and fauna.
Guest suite in Pickering
4.8 out of 5 average rating, 215 reviews

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!

Guest favourite
A modern kitchen is featured with sleek cabinetry and a breakfast bar, accompanied by four dark leather chairs. A cozy living area includes a large sectional sofa facing a mounted flat-screen television. Warm lighting enhances the ambiance of the space.
Home in Pickering
4.96 out of 5 average rating, 27 reviews

Modern Basement Apartment

**Modern Basement Apartment - Affordable Luxury with Sauna!** Enjoy this stylish basement apartment featuring chic pot lights and a luxurious washroom, complete with a relaxing sauna. Perfectly located near a movie theater, shopping mall, and restaurants, it offers privacy and convenience. Free parking included, and with a five-star rating, you can expect top-notch service. Book your stay today!

Popular amenities for Pickering holiday rentals

When is the best time to visit Pickering?

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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 € 9 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

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Durham Region
  5. Pickering