Holiday rentals in Pickering

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Top-rated holiday rentals in Pickering

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The image displays a suite featuring a spacious bed with floral bedding, a cozy half living room with a television, and an outdoor patio area surrounded by potted plants. Comfortable seating on the patio invites relaxation in the peaceful backyard, enhancing the overall living space.
Guest suite in Pickering
4.73 out of 5 average rating, 399 reviews

King Studio Suit W/parking+1st flr wlkout

Moonlight Meadow provides you this 1st floor Elegant suite with walkout door to the beautiful backyard. This unit includes one spacious bed room with a half living room,kitchenette(no kitchen)laundry room and a private bathroom.This place is a part of a 3 storey building.The 1st level will be for the guests with a private keyed to the unit with a self check in option (only main entrance is shared but guest will get a key for it)Also the suite includes a comfy king bed,and a convertible sofa bed

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, 337 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
4.99 out of 5 average rating, 67 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.

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, 146 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, 734 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

Guest favourite
A bright bedroom features a spacious bed with dark bedding, accented by light throw pillows. Nightstands with lamps are situated on either side. Large windows allow natural light, with curtains softly framing the view of the neighborhood outside.
Guest suite in Pickering
4.94 out of 5 average rating, 48 reviews

40min DT Toronto | PickeringGO|Lakeridge SkiResort

Welcome to our modern Pickering suite perfect for families, professionals, or leisure travelers. This newly built 3-bedroom, 2.5-bathroom suite offers memory foam beds, high-speed Wi-Fi, a Smart TV, an ensuite master bath, and dedicated workstations. Enjoy a chef-inspired kitchen, a cozy patio, and free street parking. Located less than 40 mins from downtown Toronto, our home offers easy access to numerous attractions, including golf courses, ski resorts, beaches, the zoo, a casino, and spas.

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, 531 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, 114 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!

Top guest favourite
A bedroom features a spacious bed adorned with a crisp white quilt and an orange throw. Two green decorative pillows are placed on the bed. A nightstand with a lamp is positioned beside the bed. A framed botanical artwork decorates the wall.
Guest suite in Ajax
5 out of 5 average rating, 14 reviews

Peaceful Escape to Town of Lakes

Brand new and bright basement apartment in Ajax, Just minutes’ drive to waterfront and conservation areas. Walking distance to outlet shopping mall, restaurants, and trail. Golf center, race track, and casinos are within 10-minute drive. Ski resorts and Toronto Zoo are within 20-minute drive. Separate entrance, self check in. One bed room with attached bathroom, and queen-size bed. Living room with a powder room has futon which can be converted to a sofa bed. Private Kitchen and laundry.

Guest favourite
Guest suite in Pickering
4.91 out of 5 average rating, 258 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, 84 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.

Popular amenities for Pickering holiday rentals

When is the best time to visit Pickering?

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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
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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

Destinations to explore

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