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Holiday houses in Pickering

Find and book unique accommodation on Airbnb

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
The sleeping area is defined by a cozy queen bed, featuring decorative pillows with intricate patterns. Soft lighting is provided by wall-mounted lamps on either side, against a calming blue accent wall. Minimalist artwork is displayed above the bed, enhancing the space's modern design.
Guest suite in Pickering
4.96 out of 5 average rating, 185 reviews

Private | WiFi | Q Bed | TV | Desk | Cafe | Park

- Free street parking - Great pitstop for travels along the 401 (exit 399) - Open concept space with private bathroom - Queen bed, fast Wi-Fi, and mini kitchen bar - Kettle, microwave, and coffee station included - Cozy workstation for remote work or email - Convenient location near transit, shops and restaurants - Pickering Casino (10 min drive), Pickering Golf club (2 min drive), Bubble tea, Rollz Ice Cream, Good Life, Shawarma, Mexi Guac within a 4 min drive -A cozy ~200 sq ft resting place

Top Guest favourite
Home in Pickering
4.93 out of 5 average rating, 371 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!

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, 759 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
The cozy living area features a plush gray sofa adorned with yellow throw pillows and a coordinating blanket. A stylish coffee table sits centrally, surrounded by two bright yellow armchairs. A smart TV is mounted on a marbled wall, enhanced by warm ambient lighting.
Apartment in Ajax
4.98 out of 5 average rating, 43 reviews

Tranquil Haven: Luxurious 2BR Retreat Near Hwy 401

Your search for the perfect two-bedroom legal basement apartment ends here! Designed with comfort and style in mind, this meticulously maintained and tastefully decorated space offers a peaceful retreat for travelers seeking a home away from home. With a fully equipped kitchen, a cozy living area, and two bedrooms with comfortable queen beds, you'll have everything you need. Plus, our convenient location and nearby amenities make it the ideal choice. Look no further, this is the place for you!

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.
Guesthouse in Pickering
4.97 out of 5 average rating, 103 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.

Top Guest favourite
The living room features two couches, one convertible into a bed, surrounding a coffee table. A fireplace is situated to the left, with a stack of wood beside it. A wall-mounted TV is visible, enhancing the space's functionality for relaxation and entertainment.
Guest suite in Pickering
4.97 out of 5 average rating, 101 reviews

Luxury Suite w/ Cafe & Sauna in Pickering

We welcome you to stay at our luxury suite that is perfect for a vacation retreat, visiting family/friends or for a business trip. Enjoy your own in-suite café, sauna, and fireplace. Our serene space will leave you relaxed from the very start to the end of your stay. There's plenty of room for yoga or stretching. Located just walking distance to Pickering’s beautiful waterfront, minutes to HWY 401, shopping, restaurants, and the GO Train Station that can take you to Downtown Toronto & more!

Top Guest favourite
Guest suite in Ajax
4.96 out of 5 average rating, 551 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
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, 122 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.
Apartment in Pickering
4.92 out of 5 average rating, 221 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.

Guest favourite
Apartment in Pickering
4.94 out of 5 average rating, 17 reviews

Pool/ King Bed/Wifi/Toronto LakeView/Free Parking

The Shopping & Dining Retreat Shop, dine, and relax in style. This chic 1-bedroom condo features high-end décor, a queen pull-out sofa, and a full kitchen. 🛍️ Just steps from a vibrant mall and countless restaurants. 🚆 Toronto is only 23 minutes away via GO. Perfect for weekend getaways, foodie trips, or retail therapy. Secure your dates now and enjoy the ultimate mix of comfort and city convenience!

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, 157 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

Top Guest favourite
A light-filled living area features a yellow sofa, an accent chair, and a wooden coffee table. The kitchenette is equipped with white cabinetry, and a small dining table adds functional space. Decorative items such as art and plants complement the serene environment.
Guesthouse in Pickering
5 out of 5 average rating, 66 reviews

Wildflower by The Bay

After a day spent by Frenchman's Bay, put your feet up in our serene backyard hideaway! A quick walk to Lake Ontario, a handful of great restaurants, bars, shops, and the expansive and scenic Waterfront Trail, this location is unbeatable. The Pickering Go Station less than a 20-min walk (or a short drive) away, bringing you to the heart of downtown Toronto in 40 minutes.

Popular amenities for Pickering holiday rentals

When is the best time to visit Pickering?

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Avg. price$103 NZD$105 NZD$106 NZD$110 NZD$118 NZD$121 NZD$126 NZD$130 NZD$120 NZD$118 NZD$113 NZD$116 NZD
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Frequently Asked Questions

  • How much does it cost to stay in apartment rentals in Pickering?

    Experience the best of Pickering with our apartment 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 condo rentals in Pickering have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • Do bungalow rentals in Pickering have a kitchen?

    Absolutely! We offer over 40 bungalow rentals with a kitchen in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Pickering?

    Enhance your stay in our House Rentals with the most popular amenities: over 960 homes with air conditioning, over 880 homes with free parking, over 980 homes with wifi, over 900 homes with a kitchen, 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 house rentals in Pickering have air conditioning?

    Absolutely! We offer over 960 house 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 360 vacation rentals in Riverside, over 120 vacation rentals in Lakeside, and over 1,450 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 1,630 holiday rentals in Pickering

  • Nightly prices starting at

    Pickering holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 42,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    650 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 270 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    1,000 properties have a dedicated workspace

  • Wi-Fi availability

    1,590 of Pickering holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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
  5. Pickering