Vacation rentals in Pickering

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Top-rated vacation 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, 181 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
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, 747 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.
Guesthouse 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.

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, 100 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
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
4.85 out of 5 average rating, 118 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!

Superhost
A modern living area features a gray sectional sofa and two light-colored chairs positioned around a glass coffee table. A wall-mounted television is situated above a contemporary electric fireplace, with a decorative plant adding a touch of greenery to the space.
Guest suite in Whitby
4.81 out of 5 average rating, 128 reviews

Luxury 2 Bedroom Apartment - 5 mins to Thermea Spa

★ "Very nice apartment! Clean, spacious, and modern'' ★ ☞ Fully Private unit!!! ☞ Fully equipped kitchen!!!! With all required machines and pots ☞ Extended Kitchen Island ☞ All rooms w/ queen + Sheets and Duvet !!!!!! ☞ 55” smart Samsung TV w/ Netflix + Samsung sound bar with Sub ☞ Central AC + Heating ☞ Onsite washer + dryer ☞ Parking → 1 on the driveway!!!! ☞ 700mbps wifi ☞ Open Concept 5 mins → Thermëa spa village 12 mins → Whitby and 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, 104 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 welcoming home features a well-maintained exterior surrounded by lush green trees. The entrance is adorned with a small balcony and pathway, inviting guests into a bright living space. The design balances modern elements with natural landscaping, creating an inviting first impression.
Apartment in Pickering
4.82 out of 5 average rating, 125 reviews

Peaceful & Private Karma Stay, Easy Toronto Access

Relax in the spacious, newly renovated basement with a separate entrance. As hosts, we take pride in being approachable and friendly. Having spent our own fair share of time away from home since a young age & exploring different places, we deeply understand the importance of providing a warm & peaceful environment for our guests. Your comfort and well-being are our top priorities, and we're here to ensure your stay feels like a welcoming home.

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
4.93 out of 5 average rating, 216 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
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, 218 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

Top guest favourite
Apartment in Windfields
4.96 out of 5 average rating, 159 reviews

Family Friendly | HOT TUB | Near Toronto & UOIT

Newly built 1-bedroom private basement apartment in Oshawa featuring a work/study area, full kitchen, and in-suite laundry. Relax in the hot tub after exploring local trails, parks, and farms. Close to Ontario Tech University, Durham College, shops, and restaurants. Easy access to Durham Transit, GO Bus/Train, and Highway 407. Ideal for couples, professionals, or small families.

Popular amenities for Pickering vacation rentals

When is the best time to visit Pickering?

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Frequently Asked Questions

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

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

    Absolutely! We offer over 150 apartment rentals with wifi in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Pickering have a kitchen?

    Absolutely! We offer over 10 guesthouse 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 880 homes with free parking, over 900 homes with a kitchen, over 980 homes with wifi, over 960 homes with air conditioning, 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 1,400 vacation rentals in Malvern, over 120 vacation rentals in Lakeside, and over 340 vacation rentals in Riverside.

  • 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 vacation rentals in Pickering

  • Total vacation rentals

    Explore 1,540 vacation rentals in Pickering

  • Nightly prices starting at

    Pickering vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 40,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    620 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 270 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    940 properties have a dedicated workspace

  • Wifi availability

    1,510 of Pickering vacation 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