Vacation rentals in Pickering

4.93 out of 5 average rating, 304 reviews

A modern kitchenette is shown, featuring a silver refrigerator and a stainless-steel microwave above the stove. Light cabinetry contrasts with a wood countertop. A gray sofa sits in the foreground, accompanied by a wall clock and a lamp, enhancing the sleek and organized space.

Condo in Pickering

“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!

4.99 out of 5 average rating, 131 reviews

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

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. 30 min 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 village

5 out of 5 average rating, 115 reviews

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

Ultra-Modern Luxury Retreat! Close to Thermea SPA.

Cozy and welcoming, located in a quiet and family-friendly neighborhood; it is a terrific offering that will impress guests. It is centrally located in Ajax and 10 min from Thermea Spa, newly built with deluxe finishes situated within walking distance to superb services, including groceries, parks, and shops. The space is approximately 1,000 sq. ft in total, with in-floor heating. The modern electric fireplace sits in front of the expansive couch, with a TV with Netflix and Prime Video access.

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.

4.87 out of 5 average rating, 704 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

4.98 out of 5 average rating, 88 reviews

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

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.

The open layout features a living area with a blue sofa bed facing a large TV, while a dining table for two is positioned nearby. A well-equipped kitchen with modern appliances, including a refrigerator and stove, is visible. Natural light comes in through a row of windows above.

4.92 out of 5 average rating, 12 reviews

Basement Apt w/ Full Kitchen, Netflix, & Work Area

Cozy and budget-friendly private 1BR suite, ideal for long stays! Conveniently located 3-4 minutes off Hwy 401, 2 minutes from Pickering GO Station, and just a short drive to the beach. Enjoy easy access to 5+ grocery stores and a shopping mall within a 10-minute drive. Unwind with a large TV and Netflix, or prepare meals in the small kitchen with all the essentials. Queen bed provides a comfortable night's sleep for solo travelers or couples alike. Perfect for an affordable, extended stay!

A welcoming living area features two leather sofas paired with a light-colored end table and a lamp. Large glass doors open to a private yard, while natural light brightens the space through multiple windows adorned with decorative curtains.

4.92 out of 5 average rating, 48 reviews

Beautifully renovated apartment

Located on a quiet cul-de-sac right beside the popular Seaton Trail. Self-check into your beautiful walk-out apartment. Relax and watch the birds in the back yard. Parking included. Large windows provide natural light. There are 2TV's !Netflix and Amazon Prime). The bedroom has a queen bed. Elegant bathroom with oversized shower. Easy access to downtown Toronto, by transit or highway. A short drive to numerous shops and excellent restaurants, a huge new casino, and Toronto Zoo.

An outdoor patio area features a dining table surrounded by comfortable chairs. Ambient string lights create a warm glow above, complemented by decorative umbrella and lounge chairs. Lush greenery is present alongside a hot tub, enhancing the inviting atmosphere of the space.

4.91 out of 5 average rating, 238 reviews

Urban HotTub Oasis/Separate Entrance/Unit/DT 30min

Completely private studio suite with cozy queen bed and 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. Safe and secure with a disclosed entrance camera and responsive hosting

Superhost

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.

4.79 out of 5 average rating, 200 reviews

Muskoka on the City

Property situated on Rouge National Urban Park, close to Toronto zoon, seaton trail. step to beautiful lake and beach , you will enjoy hiking,kayak ,bike and fishing.Close to highway,resultant,shopping mall,public transport, Rouge Hill GO Station. bright in ground suite .kitchen ,dinning room in basement with TV, private bathroom(basement), and private entrance(back yard). Suite has a separate bedroom with a queen sized bed, free wireless internet, and full laundry.

5 out of 5 average rating, 6 reviews

A cozy living area is furnished with a light-colored sofa and a wooden coffee table centered on a soft rug. A large mirror is mounted on a wooden wall unit, which features cabinets for storage. Bright lighting enhances the warm tones of the wooden flooring.

Guesthouse in Pickering

Beautiful Private Guest House

This beautiful one bedroom unit is great for a romantic getaway and it's 5 min driving to Frenchman's Bay Beach. The private patio is beautiful with space to relax and enjoy. Separate entrance from the main unit. Utilities and wifi included. Wifi and TV with free Netflix and Crave installed. The kitchen is spacious with full appliances, Fridge, Stove, Microwave, Dishwasher, Coffee maker, Toaster and Kettle. Dishes and cookware are available in the kitchen.

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.

4.84 out of 5 average rating, 102 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.

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.

4.92 out of 5 average rating, 191 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.

Vacation rentals for every style

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A space thats all yours, with room for everyone

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Quaint homes, peaceful surroundings

Popular amenities for Pickering vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Pickering

A light-filled living area showcases a comfortable sofa adorned with a plaid pattern. A small plant sits on the coffee table, while a blue accent table and a television are visible nearby. Mirrored closet doors reflect the serene color palette of the walls.

4.97 out of 5 average rating, 66 reviews

Relaxing Private 1-bdrm apt Surrounded by Nature

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.

4.98 out of 5 average rating, 84 reviews

Luxury Suite w/ Cafe & Sauna in Pickering

4.98 out of 5 average rating, 47 reviews

A contemporary living area is shown, featuring a plush green sofa and a round wooden coffee table. A flat-screen TV is mounted on the wall, with a modern lamp and a potted plant adding character to the space. Soft lighting creates a relaxed ambiance.

Apartment in Ajax

Miden Touch: Stylish Modern Basement w/ Workspace

4.78 out of 5 average rating, 96 reviews

A three-story luxury house is shown, featuring a stone facade and large front steps. Lush greenery surrounds the property, and the well-maintained street leads towards the nearby beach. Clear blue skies create a bright and inviting atmosphere.

Home in Pickering

Beach House: First Floor

4.94 out of 5 average rating, 47 reviews

A cozy living area is presented with a comfortable blue sofa positioned around a coffee table. A 55-inch Smart TV is mounted on the wall opposite. A stylish mirror and decorative accents add to the warm ambiance. The space is well-lit with natural light from the door.

Home in Ajax

Cozy 1-Bedroom Retreat

A bright bedroom features a spacious bed with dark bedding, accented by light throw pillows. Nightstands with lamps are situated on either side. Large windows allow natural light, with curtains softly framing the view of the neighborhood outside.

4.93 out of 5 average rating, 27 reviews

40min DT Toronto | PickeringGO|Lakeridge SkiResort

An open living area is presented, featuring a comfortable sofa and a wooden coffee table, with a decorative plant on a side table. The modern kitchen is visible in the background, equipped with sleek appliances. Natural light fills the space from nearby windows.