Vacation rentals in Pickering

4.96 out of 5 average rating, 181 reviews

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

- 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

4.93 out of 5 average rating, 360 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!

4.87 out of 5 average rating, 749 reviews

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

* 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

4.97 out of 5 average rating, 103 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.

4.97 out of 5 average rating, 35 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

5 out of 5 average rating, 3 reviews

Home in Whitby

Entire Detached House; 2 Bedrooms; 3 Parkings

Enjoy a completely independent, bright, and peaceful detached house in a safe, family-friendly neighborhood-perfect for relaxation or adventure. Located just 6 minutes from Ontario’s largest thermal spa, Thermea Spa Village Whitby, and close to ski resorts (Lakeridge 20 min, Dagmar 16 min), this home is ideal for spa lovers, families, and winter-sport getaways. Three parking spots! Although this is a new listing, we’ve been hosting another property on Airbnb for two years with a 4.91 rating.

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.

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!

5 out of 5 average rating, 20 reviews

A bedroom features a spacious bed adorned with a crisp white quilt and an orange throw. Two green decorative pillows are placed on the bed. A nightstand with a lamp is positioned beside the bed. A framed botanical artwork decorates the wall.

Guest suite in Ajax

Peaceful Escape to Town of Lakes

Brand new and bright basement apartment in Ajax, Just minutes’ drive to waterfront and conservation areas. Walking distance to outlet shopping mall, restaurants, and trail. Golf center, race track, and casinos are within 10-minute drive. Ski resorts and Toronto Zoo are within 20-minute drive. Separate entrance, self check in. One bed room with attached bathroom, and queen-size bed. Living room with a powder room has futon which can be converted to a sofa bed. Private Kitchen and laundry.

4.98 out of 5 average rating, 109 reviews

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

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.

4.79 out of 5 average rating, 29 reviews

A compact kitchen area features modern appliances, including a stainless steel stove and a microwave. A wooden table with two black stools provides a functional dining space. Light-colored walls and bright ceiling lights create a welcoming ambiance.

Guest suite in Pickering

GTA Suite | Lakeridge Ski Resort | Pickering GO

Welcome to our cozy studio, perfect for couples or professionals! The space includes a folding queen bed for flexibility, a dining table that doubles as a desk, and a portable couch. Enjoy shared laundry access, high-speed Wi-Fi, a smart TV, and free parking. Located less than 15 minutes from Pickering GO Station, our unit offers easy access to the GTA and is close to attractions like golf courses, ski resorts, beaches, the zoo, a casino, and spas.

5 out of 5 average rating, 125 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 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.

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.

4.94 out of 5 average rating, 147 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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Pickering

5 out of 5 average rating, 25 reviews

A bright, private bedroom features a spacious bed with a light-colored comforter and a yellow accent pillow. A desk with a lamp and a chair is positioned nearby. Natural light enters through a window, highlighting the room's neutral tones and wooden flooring.

Private room in Markham

Weekly OFF, Parking, Private Living Room & Bath!

4.81 out of 5 average rating, 108 reviews

Cozy Private Room & Bathroom Pickering

Private room in Scarborough

A modern kitchen is equipped with stainless steel appliances, including an electric stove and a refrigerator. White cabinetry and a designer backsplash emphasize the clean lines. Natural light enters through a window, and a front door with decorative glass is visible in the background.

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MK Pickering

5 out of 5 average rating, 5 reviews

A well-appointed kitchen features white cabinetry and a minimalist design. An electric stove is situated next to a dual sink, with utensils and dishware neatly arranged on the countertops. Natural light illuminates the space, enhancing the crispness of the white and grey color scheme.

Private room in Lakeview

Budget-friendly private bedroom Oshawa

5 out of 5 average rating, 4 reviews

Stylish Bedroom in Modern Pickering Home

4.9 out of 5 average rating, 123 reviews

A bright bedroom features a spacious bed with a floral-patterned comforter and yellow accent pillows. Natural light floods in through two windows, illuminating a geometric area rug on the floor. A dresser is placed beside the bed, contributing to a clean and minimalistic design.

Private room in Ajax

Room in Ajax with en-suite washroom