Vacation rentals in Pickering

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Top-rated vacation rentals in Pickering

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Top guest favorite
Home in Pickering
4.93 out of 5 average rating, 390 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 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, 772 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, 107 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
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, 103 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!

Guest favorite
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
4.97 out of 5 average rating, 172 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.

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, 119 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
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
4.99 out of 5 average rating, 146 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 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
4.99 out of 5 average rating, 142 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, 225 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 favorite
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, 127 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 favorite
A spacious living area features a large sectional sofa paired with a modern armchair. Natural light streams through the expansive windows, highlighting a round coffee table and a light-toned area rug underneath. A potted plant adds a touch of greenery to the serene space.
Home in Pickering
4.88 out of 5 average rating, 126 reviews

Serene Stays - Pickering (5Beds, 2.5Baths, 4Park)

Welcome to Serene Stays - Pickering, where you'll find comfort, style, and convenience all come together! This is a newly built, spacious 4 bedroom, 2 storey home where you can completely relax with access to the entire home - boasting 4 bedrooms, 2.5 bathrooms, living room, dining room, full kitchen, private outdoor patio, and laundry room. This home has 4 parking spaces and is perfect for large families or groups!

Top guest favorite
A modern kitchen area features sleek gray cabinets and stainless steel appliances. A dining table is set for four, complete with neatly arranged plates and glassware, inviting shared meals. The kitchen backdrop displays a contemporary black and white patterned wall, enhancing the space's clean aesthetic.
Guest suite in Pickering
4.95 out of 5 average rating, 109 reviews

RedDore - 2 Bedroom Cozy Basement Suite

Enjoy the charming touches of this spacious basement suite with a clean modern feel. Beautifully decorated featuring a spacious living/dining room combo area, and a brightly lit bathroom with a stand-up shower. This guest suite with your very own private entrance is luxurious and full of warmth. Along with our beautiful accomodations we have car rentals available to make your trip complete. Just ask for details.

Popular amenities for Pickering vacation rentals

When is the best time to visit Pickering?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$12,966 GYDG$13,175 GYDG$13,384 GYDG$13,802 GYDG$14,848 GYDG$15,266 GYDG$15,894 GYDG$16,312 GYDG$15,057 GYDG$14,848 GYDG$14,221 GYDG$14,639 GYD
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Frequently Asked Questions

  • Are there family-friendly townhouse rentals in Pickering?

    Pickering has more than 30 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Pickering with our condo rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly bungalow rentals in Pickering?

    Four-legged friends are welcome in Pickering. Choose from more than 10 bungalow rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Pickering?

    Yes! Work meets play with ease at over 650 house rentals in Pickering featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Pickering vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 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 120 vacation rentals in Lakeside, over 1,450 vacation rentals in Malvern, and over 360 vacation rentals in Riverside.

  • Do condo rentals in Pickering have air conditioning?

    Absolutely! We offer over 10 condo rentals with air conditioning 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.

  • Do bungalow rentals in Pickering have wifi?

    Absolutely! We offer over 60 bungalow rentals with wifi in Pickering. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Pickering have free parking?

    Absolutely! We offer over 140 apartment 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 G$2,091 GYD 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