
Holiday rentals in Pickering
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Top-rated holiday rentals in Pickering
Guests agree: these stays are highly rated for location, cleanliness and more.

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

“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!

* 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

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.

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

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!

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.

Modern Retreat near Waterfront!
Modern 2BR in Pickering with a glowing queen bed, full-length mirrors, workspace, and built-in charging ports. Second bedroom has light-up full-size bunk beds and charging ports. Spa-style bath with waterfall + handheld shower. Full kitchen with coffee/tea station & complimentary drinks. Cozy living room with sectional + 55” Roku TV. Washer/dryer, keyless entry. Family-friendly, near lakefront, GO stations & malls. Stylish comfort in a perfect location—book your stay today!

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)

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.

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!

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 holiday rentals
Stay near Pickering's top sights
Other great holiday rentals in Pickering

Weekly OFF, Parking, Private Living Room & Bath!

Weekly OFF! Private Kitchen & Bathroom, Markville

Budget-friendly private bedroom Oshawa

Private Bedroom Private Bathroom

Brand New Guest Room in Basement

Comfy Room • Centennial College [Shared Bathroom]

R3 - Private and cozy

Studio by the woods
When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $80 SGD | $81 SGD | $82 SGD | $85 SGD | $91 SGD | $94 SGD | $98 SGD | $100 SGD | $92 SGD | $94 SGD | $91 SGD | $87 SGD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
Frequently Asked Questions
How much does it cost to stay in private suite rentals in Pickering?
Experience the best of Pickering with our private suite 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 apartment rentals in Pickering have wifi?
Absolutely! We offer over 150 apartment rentals with wifi 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.
What are the most popular amenities for House Rentals in Pickering?
Enhance your stay in our House Rentals with the most popular amenities: over 880 homes with free parking, over 900 homes with a kitchen, over 980 homes with wifi, over 960 homes with air conditioning, 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 guesthouse rentals in Pickering have air conditioning?
Absolutely! We offer over 10 guesthouse 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 1,400 vacation rentals in Malvern, over 120 vacation rentals in Lakeside, and over 340 vacation rentals in Riverside.
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 holiday rentals in Pickering

Total holiday rentals
Explore 1,540 holiday rentals in Pickering

Nightly prices starting at
Pickering holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 40,310 verified reviews to help you choose

Family-friendly holiday rentals
620 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 270 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
940 properties have a dedicated workspace

Wifi availability
1,510 of Pickering holiday rentals include wifi 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
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- BMO Field
- Toronto Zoo
- Toronto Eaton Centre
- Trinity Bellwoods Park
- Massey Hall
- Financial District
- Casa Loma
- Dufferin Grove Park
- Toronto City Hall
- Rouge National Urban Park
- Christie Pits Park
- Royal Ontario Museum
- Royal Woodbine Golf Club
- Lakeridge Ski Resort




