Holiday rentals in Pickering

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Top-rated holiday rentals in Pickering

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

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Top guest favourite
Apartment in Pickering
4.94 out of 5 average rating, 349 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 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, 745 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 modern living space is highlighted by a spacious bed and an entertainment area featuring a large wall-mounted TV. A cozy seating arrangement includes a soft couch and a stylish armchair. Ambient lighting is provided by a chandelier above, complemented by a decorative fire feature.
Guest house in Pickering
4.97 out of 5 average rating, 101 reviews

Luxury Ground-Level "Suite Escape"

"Suite Escape" offers a luxurious private guest suite in Pickering, Ontario. Fully equipped w/ a cozy Queen Bed, spa bathroom, workstation, 65” TV, A/C, fireplace, & kitchenette. Conveniently located to Hwy 401 & 407, GO Train, Durham Transit, malls, cinemas, casinos, waterfront & hiking trails, golf courses + wineries within a short walk or drive. Downtown Toronto & Pearson Airport is 30-40 mins away. Immerse yourself in luxury, tranquility, and easy access to the best of Pickering and beyond.

Superhost
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
4.96 out of 5 average rating, 152 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. Drive or GO 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.

Top guest favourite
Guest suite in Ajax
4.96 out of 5 average rating, 539 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.

Top guest favourite
The living room features a large sectional sofa and a coffee table with a decorative plant. A modern gas fireplace is situated beneath a wall-mounted television displaying a streaming service. Sunlight fills the space through multiple windows, creating a bright and cozy atmosphere.
Home in Pickering
4.98 out of 5 average rating, 132 reviews

4BR |Chef Kitchen| Casino Dagmar Thermea (15km)

Why you will love your stay here: - ***ENTIRE HOME*** No one will be on the property but those on the booking. This is a DETACHED house. No connecting houses. - Open concept on the main floor so you can connect and create memories - Dedicated work from home spaces . Cat 6 ports -The 2nd floor has 4 different rooms where you can unwind and take a much deserved break - 10ft ceilings on a corner lot with lots of sunlight - Central Hub to Toronto (45 min drive)

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, 100 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.

Guest favourite
A cozy living area is presented with a grey sofa adorned with yellow cushions. A large TV is mounted on the wall, facing a white coffee table on a textured rug. A colorful abstract painting decorates one wall, complemented by a small indoor plant.
Flat in Pickering
4.93 out of 5 average rating, 215 reviews

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.

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, 124 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.

Guest favourite
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, 217 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!

Top guest favourite
A modern living space is displayed, featuring a wall-mounted television above a sleek dark cabinet. To the right, a laundry area is visible with stacked washer and dryer units. Light hardwood flooring runs throughout the space, contributing to a clean and contemporary look.
Home in Pickering
4.94 out of 5 average rating, 144 reviews

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

Guest favourite
A modern living area features a pair of vibrant blue sofas arranged around a decorative area rug. Large windows allow natural light to brighten the space, complemented by a sleek kitchen with dark cabinetry and stainless steel appliances visible in the background.
Home in Whitby
4.86 out of 5 average rating, 209 reviews

Luxurious & Modern Guest Suite-Walkout Bsmt Apt.

Luxurious new constriction basement apartment in central Whitby. Gorgeous kitchen, living area, and laundry. Ravine lot with excellent views of forest nearby. One stunning bedroom and one 3pc bath. One Free parking on the premises! Please keep in mind we do have a dog on the property. Please note: The kitchen only has a wine fridge. We do not have a freezer.

Popular amenities for Pickering holiday rentals

When is the best time to visit Pickering?

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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 £7 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