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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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Superhost
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, 420 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 favorite
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, 183 reviews

Private | WiFi | Q Bed | TV | Desk | Café | 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 favorite
Home in Pickering
4.93 out of 5 average rating, 366 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 favorite
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, 754 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 favorite
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.

Guest favorite
Guest suite in Pickering
4.91 out of 5 average rating, 273 reviews

Urban HotTub Oasis/Separate Entry/Suite/DT 30 min

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 or smaller. Trucks will not fit. Safe and secure with a disclosed entrance camera and responsive hosting

Top guest favorite
Guest suite in Pickering
4.92 out of 5 average rating, 13 reviews

The Reytan Retreat

Welcome to your stylish 1-bedroom basement apartment in Pickering with queen bed, open living area, smart TV, full kitchen, modern bath, in-suite laundry, work desk, and private entrance. Located in a quiet neighborhood near shops, dining, Frenchman’s Bay, and Pickering Town Centre. Quick access to Hwy 401, transit, and GO Station for trips to Toronto. Explore nearby trails, beaches, Durham Live, and Rouge National Urban Park. Perfect for business or leisure, offering comfort and convenience.

Top guest favorite
Guest suite in Ajax
4.96 out of 5 average rating, 548 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 favorite
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, 114 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 favorite
A modern living space features a comfortable gray couch and two stylish lamps on side tables. A coffee table sits at the center, with a small dining area visible in the background. Natural light enters through large windows, enhancing the warm ambiance.
Guest suite in Ajax
4.78 out of 5 average rating, 125 reviews

Adorable 1-bedroom with free parking on premises

Forget your worries in this spacious and serene space. Enjoy this cozy, modern guest suite with a private bathroom, kitchen, workspace, HD TV with alexa fire stick Amazon Prime and fast wifi. Perfect getaway, 5 minutes walk to Ajax Waterfront Park and close to Casino Ajax, Rotary Park and general hospital. Note that this is a guest suite as a part of the main house where the landlord and their family live.

Superhost
Apartment in Pickering
4.93 out of 5 average rating, 14 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 favorite
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, 150 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

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 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 vacation rentals in Pickering

  • Total vacation rentals

    Explore 1,630 vacation rentals in Pickering

  • Nightly prices starting at

    Pickering vacation rentals start at € 9 per night before taxes and fees

  • Verified guest reviews

    Over 42,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    650 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 270 rentals that welcome pets

  • Vacation 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 vacation rentals include wi-fi 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
  5. Pickering