Vacation rentals in Pickering

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Top-rated vacation rentals in Pickering

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Guest favorite

Guest suite in Pickering

4.89 out of 5 average rating, 106 reviews

*Hotub* Walkout Patio* Separate Unit* Inlaw Suite!

Oasis of country & city life in North Pickering!! We offer an above ground (main floor) fully private in law suite in greater Toronto with a separate entrance! 8 min drive to train station to Toronto & half hour drive to downtown Toronto. Amenities include: free parking for a SUV size car, wifi, 4K tv/cable, air conditioning, fridge, keurig, kettle, microwave/air fryer, laundry, garden patio! and ***Jacuzzi ***Hotub with jets and LED lights 10-15 min drive to local attractions in listing pics!!

Jun 6 – 13

ﺩ.ﺇ357 per night

Guest favorite

Guest suite in Pickering

4.94 out of 5 average rating, 124 reviews

Separate 2 Bedroom & 2 Washroom up to 4 people.

Hotel-style apartment in a home annex. Not a basement. The apartment has 2 bedrooms with attached washrooms, Living area, kitchen, dining. Our property accommodates up to 4 people. Children are welcome to stay. Conveniently located just off Highway 401. Close to downtown Pickering, Go Station, mall, restaurants. We are a good stopover point if you are traveling to downtown Toronto which is only a 40 min drive. Note: Show us your ID when "Checking In" and it has to match with your booking name.

Jun 14 – 21

ﺩ.ﺇ401 per night

Superhost

Home in Pickering

5.0 out of 5 average rating, 4 reviews

New legal private studio apartment

Brand new legal private basement suite is suitable for couples/solo adventurers/business travellers. It has separate independent entrance & comes with a full size bathroom, fully equipped kitchen, queen bed w memory foam mattress, private laundry, wardrobe & high speed internet. Parking available. 2 mins drive to highway 401, YYZ airport is 30 mins away & takes 35 mins to reach Toronto downtown. 50 mtrs to bus stop, 5 mins drive to Pickering GO & less than 100 steps to gas station/grocery store.

May 2 – 9

ﺩ.ﺇ204 per night

Guest favorite

Apartment in Whitby

4.95 out of 5 average rating, 152 reviews

Serenity Suite w/Sauna-Your Entire Apt Awaits You

LONG-TERM stays welcome. A short drive to Thermea Spa Village. This is a beautiful, newly renovated, spacious basement apartment, perfect for two. Located in Whitby Shores (w/ hot tub) just a few minutes’ walk to Lake Ontario, a park, & trails, the house is situated in a quiet and friendly neighbourhood. It is close to all amenities - shopping, movie theatre, and other entertainment options, restaurants, GO Train station, Hwy 401, and easy access to Hwy 407. We look forward to meeting you!

Oct 22 – 29

ﺩ.ﺇ286 per night

Guest favorite

Home in Pickering

4.78 out of 5 average rating, 55 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!

Oct 21 – 28

ﺩ.ﺇ505 per night

Guest favorite

Guesthouse in Pickering

4.86 out of 5 average rating, 110 reviews

Hotel 65. Our Spacious 2-Bedrm Basement w/Parking

Stunning, spacious, cozy basement apartment . Open concept living/dining room with kitchen. The larger room offers a queen bed and a futon for additional sleeps. The second has two twins that can be setup as an optional king. A TV in each room with Netflix, Prime, Disney+ and IPTV with multiple sports, North American and International channels. Many kitchen amenities. Mins to 401, Grocery, Resturants, Malls, Casinos, National Park, Toronto Zoo and only 5 minutes to GO Train. Book & Enjoy!

Mar 18 – 25

ﺩ.ﺇ274 per night

Guest favorite

Guest suite in Ajax

4.95 out of 5 average rating, 394 reviews

Walk Out Basement Apartment W/Separate Entrance

PRIVATE Walk Out Basement Apartment W/Separate Entrance. 420 Sq.Ft space. Queen Sized Bed. Oversized Shower w/ Rainfall Shower-head. Small Kitchenette w/ Microwave, TWO Mini Fridges, Coffee/Hot Water Tea Maker. Dining/Work Table w/Benches. High Speed Wi-fi. Living Room w/ Reclining Lazy Boy Couch and 50” Smart Tv. Over 1000 Live Tv Channels and Netflix. Private Little Backyard Patio w/Table. Private Driveway (Parking For 2 Cars). 1 Min Drive to Hwy 401. 15 Min Walk to Ajax Go Station.

Jun 7 – 14

ﺩ.ﺇ342 per night

Guest favorite

Apartment in Pickering

4.94 out of 5 average rating, 105 reviews

Walk-out Basement Guest suite w/Fibe & Parking

My family of 4 lives upstairs and are available for any support, questions or concerns. We like to give our guests their privacy during their stay but I am available when needed. The unit comes with Bell Fibe wifi, free parking, and a tv with 1000+steaming channels, Netflix, Prime, AppleTV. Need a place to watch the game or fight?We got it! Our Airbnb is within driving distance to several popular restaurants, bars, shopping and casinos. An ideal central base to explore Pickering.

Aug 2 – 9

ﺩ.ﺇ308 per night

Guest favorite

Home in Pickering

4.84 out of 5 average rating, 150 reviews

Tranquility by the Marina | 3 Bedroom Open Concept

Relax with the whole family in the upstairs unit of this legal duplex. Equipped with a private entrance, your unit will have no shared spaces. Your stay is walking distance to the Marina, Pickering GO station and several restaurants. This 3 Bedroom residence is located within minutes to the 401 and exactly 10 minutes to the newly opened Pickering Casino. Open concept kitchen and living space is highlighted by a 65" LG OLED smart TV. This 3 PC Bathroom comes with a soaker tub.

Nov 24 – Dec 1

ﺩ.ﺇ340 per night

Guest favorite

Apartment in Pickering

4.89 out of 5 average rating, 19 reviews

A Serene & Peaceful Karma Retreat

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.

May 22 – 29

ﺩ.ﺇ281 per night

Guest favorite

Apartment in Pickering

4.91 out of 5 average rating, 107 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.

Jan 23 – 30

ﺩ.ﺇ367 per night

Guest favorite

Guesthouse in Pickering

4.94 out of 5 average rating, 16 reviews

Spacious fully private studio basement & parking

This large bachelor unit in basement is newly renovated. Fully private and separate entrance. This place is great for a romantic getaway and it's 5 min driving to Frenchman's Bay Beach. Wifi and TV with free Netflix and Crave installed. The kitchen is spacious with full appliances, Fridge, Stove, Microwave, Coffee maker, Toaster and Kettle. Dishes and cookware are available in the kitchen. Laundry is private.

Dec 14 – 21

ﺩ.ﺇ250 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Pickering vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pickering's top sights

Pickering Town Centre45 locals recommend

Toronto Pan Am Sports Centre26 locals recommend

Ajax Waterfront Park17 locals recommend

Costco Wholesale7 locals recommend

Port Union Waterfront Park10 locals recommend

Beachfront Park8 locals recommend

Other great vacation rentals in Pickering

Guest favorite

Apartment in Pickering

4.92 out of 5 average rating, 36 reviews

Rouge Valley National Park

Nov 19 – 26

ﺩ.ﺇ297 per night

Guest favorite

Guesthouse in Pickering

4.96 out of 5 average rating, 27 reviews

Luxury Ground-Level "Suite Escape"

Jul 18 – 25

ﺩ.ﺇ393 per night

Guest favorite

Home in Ajax

5.0 out of 5 average rating, 62 reviews

Ultra-Modern Luxury Retreat! Close to Thermea SPA.

Jul 3 – 10

ﺩ.ﺇ437 per night

Guest favorite

Bungalow in Pickering

5.0 out of 5 average rating, 22 reviews

Beachy bungalow

Aug 12 – 19

ﺩ.ﺇ569 per night

Guest favorite

Guest suite in Pickering

4.9 out of 5 average rating, 31 reviews

Love to Travel

Jun 10 – 17

ﺩ.ﺇ263 per night

Guest favorite

Guest suite in Pickering

4.92 out of 5 average rating, 65 reviews

Guest Suite in Pickering

Oct 28 – Nov 4

ﺩ.ﺇ593 per night

Guest favorite

Home in Pickering

4.81 out of 5 average rating, 47 reviews

Pickering Sweet Home

Apr 20 – 27

ﺩ.ﺇ402 per night

Guest favorite

Home in Pickering

4.86 out of 5 average rating, 72 reviews

Fully renovated basement

Sep 9 – 16

ﺩ.ﺇ387 per night

Show all

Quick stats about vacation rentals in Pickering

Total rentals	1.4K properties
Rentals with dedicated workspaces	880 properties have a dedicated workspace
Rentals with a pool	60 properties have a pool
Pet-friendly rentals	240 properties allow pets
Family-friendly rentals	550 properties are a good fit for families
Total number of reviews	27K reviews

Frequently Asked Questions

How much does it cost to stay in townhouse rentals in Pickering?
Experience the best of Pickering with our townhouse 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.
What are the most popular amenities for Bed And Breakfast Rentals in Pickering?
Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do private suite rentals in Pickering have a gym?
Absolutely! We offer over 10 private suite rentals with a gym in Pickering. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Pickering?
Yes! Work meets play with ease at over 880 vacation rentals in Pickering featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do bungalow rentals in Pickering have a bbq area?
Absolutely! We offer over 10 bungalow rentals with a bbq area in Pickering. Enjoy a tailored experience with all the comforts you desire.
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 550 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 60 vacation homes with pools in Pickering, available on Airbnb. Make a splash and soak up the sun in style!
Do guesthouse rentals in Pickering have wireless internet?
Absolutely! We offer over 10 guesthouse rentals with wireless internet in Pickering. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Pickering?
Make yourself at home in Pickering by choosing from our most frequently booked neighborhoods. We have over 900 vacation rentals in Morningside, over 100 vacation rentals in Pickering Beach, and over 250 vacation rentals in Port Union.

Vacation rentals in Pickering

Top-rated vacation rentals in Pickering

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Pickering vacation rentals

Stay near Pickering's top sights

Other great vacation rentals in Pickering

Apartment in Pickering

Guesthouse in Pickering

Home in Ajax

Bungalow in Pickering

Guest suite in Pickering

Guest suite in Pickering

Home in Pickering

Home in Pickering

Quick stats about vacation rentals in Pickering

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

How much does it cost to stay in townhouse rentals in Pickering?

What are the most popular amenities for Bed And Breakfast Rentals in Pickering?

Do private suite rentals in Pickering have a gym?

Are there vacation rentals with a dedicated workspace in Pickering?

Do bungalow rentals in Pickering have a bbq area?

Do guesthouse rentals in Pickering have air conditioning?

Are there family-friendly vacation rentals in Pickering?

Are there Pickering vacation rentals on Airbnb with pools?

Do guesthouse rentals in Pickering have wireless internet?

Where should I stay in Pickering?

Destinations to explore