Vacation rentals in Pickering

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Top-rated vacation 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, 414 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, 182 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

Guest favorite
Home in Pickering
4.93 out of 5 average rating, 363 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, 751 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.

Top guest favorite
Home in Pickering
4.94 out of 5 average rating, 36 reviews

Luxurious Home Away From Home

Experience comfort and luxury in this spacious home. Whether you’re here for a relaxing getaway, visiting family/friends or a business trip. Your “Home Away From Home” has all the essentials for a relaxing stay. Enjoy easy access to local attractions, shopping, dining, transit and just 1 min to the Hwy. Includes: Netflix & featured Apps, fire stick stove, toaster, fridge, microwave, kettle, Keurig coffee maker, blender Fresh towels & linens Toiletries Washer & Dryer Work space AC & Heat

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, 547 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 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!

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, 111 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 favorite
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, 218 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 favorite
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, 219 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!

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 1,540 vacation rentals in Pickering

  • Nightly prices starting at

    Pickering vacation rentals start at € 9 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 & 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

  • Wi-Fi availability

    1,510 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

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  3. Ontario
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  5. Pickering