Vacation rentals in Pickering

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.

4.96 out of 5 average rating, 183 reviews

- 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

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, 755 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

4.97 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.

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.

4.97 out of 5 average rating, 101 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!

4.91 out of 5 average rating, 276 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

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.

5 out of 5 average rating, 21 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.

4.96 out of 5 average rating, 156 reviews

A comfortable sofa in a neutral brown tone is positioned in the living room, complemented by a decorative blanket. In the background, a modern kitchen with bar stools and a light-colored counter is visible, along with a window allowing natural light into the space.

Apartment in Pickering

2 Plush Queen Beds + 1 Sofa-bed - Sleeps 6 - Apt

Spacious lower-level legal basement apartment featuring open-concept living room & kitchen. 2 queen-sized beds & 1 sofa bed. Located near the 401, grocery stores, restaurants, malls, casinos, parks, Toronto Zoo & 5-minute drive to the GO Train. 1 vehicle parking. Electric car charging $10/day Extra guests $25/day. Private side entrance for self-check in with access code. ✅ Wi-Fi, iMac & Printer ✅ TV Box with Netflix/Amazon Prime ✅Variety of Board Games ✅ Full Kitchen w/condiments

5 out of 5 average rating, 12 reviews

Home in Pickering

Luxury 2BR Townhouse• Chic Design & Top Amenities

Step into pristine luxury — a bright, clean, meticulously detailed townhouse filled with glass and crystal touches. Open, airy spaces invite you to relax in style, where every detail has been thoughtfully designed for comfort and elegance. Enjoy ultimate relaxation with our top tier home entertainment setup, complete with smart TV and full streaming access for movie nights or binge-watching. Immaculate, modern, and effortlessly inviting — your perfect escape awaits.

4.98 out of 5 average rating, 116 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.

4.78 out of 5 average rating, 125 reviews

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

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.

4.94 out of 5 average rating, 153 reviews

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

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

4.96 out of 5 average rating, 133 reviews

A bright and airy room is featured with a spacious bed dressed in light bedding. A mini fridge and microwave sit beside the bed. Natural light filters through a large window, while a small work desk and chair are positioned nearby. Decorative framed pictures adorn the wall.

Private room in Malvern

Bright Room • Centennial College [Shared Bathroom]

5 out of 5 average rating, 57 reviews

A queen bedroom is presented with a spacious bed covered in white linens and a blue throw. A window allows natural light to enter, complemented by a desk and chair, creating a functional workspace in the room.

Private room in Markham

Weekly OFF! Private Bath! Parking! Markville Mall

Superhost

Private room in Oakville

4.67 out of 5 average rating, 6 reviews

Twin bed w/shared washroom

5 out of 5 average rating, 22 reviews

Private room in Milliken

Weekly OFF, En-Suite Bath w. Sunshine!

4.95 out of 5 average rating, 19 reviews

Private room in Ajax

Private Suite & Separate Entrance. No Shared Space

Private room in Scarborough

A cozy bedroom is illuminated by ceiling lights, featuring a queen-sized bed with teal bedding. A decorative stone wall adds texture, while framed artwork enhances the decor. A small nightstand with a lamp and a flower arrangement complements the space, along with a green storage ottoman.

4.89 out of 5 average rating, 57 reviews

Private Bedroom Private Bathroom

Private room in Pickering

5 out of 5 average rating, 4 reviews

Stylish Bedroom in Modern Pickering Home