
Guesthouse vacation rentals in Pickering
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Top-rated guesthouse rentals in Pickering
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One bedroom apartment/guesthouse.
Welcome to your peaceful private getaway located north of the 401 in Whitby. Guest will have the entire apartment with separate entrance to themselves. This newly constructed apartment is equipped with a fully functional kitchen, bathroom, living room and bedroom. Apartment comes with Wifi, 43” television with Amazon Prime TV services. Guest will have a designated parking space on the driveway. Please refrain from smoking inside the unit, smoke alarm are interconnected, and are highly sensitive.

Free Parking 2BD Queen St. East
Private entrance for the separate duplex 2 bedroom apt on the upper level of our house with rooftop deck & living room easily converted into a third private bedroom. A home with lots of love put into it. Fully equipped kitchen and bathroom are stocked & ready for all your needs, TV, internet, Wi-Fi. Child friendly; crib, toys, books, DVDs, booster seat, plates, cutlery, blender. No detergent allergy worries, we use Laundry Pro a new technology that eliminates need for chemicals. Private parking.

Guesthouse w/Woodstove in Nature Near Trails & Spa
Relax and unwind at this peaceful and private guesthouse situated on 25 acres of forest. We are family friendly and invite you to roam the land and visit our resident ducks! If you are feeling more adventurous, enjoy a hike on our private onsite trail or on one of the many local trails within walking distance in the Trail Capital of Canada! Later we'll get the Woodstove lit for you (Dec - Feb). Catch up on your fav programs with Roku TV. Enjoy the therapeutic rainfall shower guests rave about!

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.

Balcony House with Separate Entrance,free Parking
Enjoy the glamour of this spacious, stylish, worry free, upscale place. It is brand new and located in the Heart of Richmond Hill, walking distance from David Dunlap Observatory Park, Plazas, Malls, Schools, Restaurants and Supermarkets. Close To Highway And Go Station, Viva, Yrt. Separate entrance and all inclusive with 1 queen bed, 1 double Sofabed if more than 2 guests, 65in smart TV, high speed wifi. Micro oven, Fridge, K-cup coffee machine, full bathroom, patio sittings, 1-2 free parking

New Entire 1 Bedroom Coach House Apartment
This completely private independent one bedroom coach house apartment is located in the prestigious Observatory Hill neighborhood in south Richmond Hill. Great for couple or small family, sleeps up to 4 people. Close to malls, public transit, restaurants, parks, library and mins to Hwy 404, Hwy 407 and Toronto. This 2nd floor apartment offers 3 Gbps internet, Nespresso coffee machine, 50 Inch Smart TV, independent AC, furnace, laundry, private entrance with lockbox access and 1 parking space.

Country Cabin Escape | King Bed | Pet Friendly
Tucked away on our peaceful family farm, this private cabin offers tranquility and comfort—while not secluded in the woods, it provides a true countryside experience. The cabin is located on the same property as our farmhouse, Country Suite, and Event Barn. Blinds are provided to enhance your privacy during your stay. The Cabin includes a full kitchen, king sized bed, propane BBQ and many other amenities, for a full list please review the "What this place offers" section of our listing.

Adorable, modern tiny home in Leslieville
Kick back and relax in this calm, stylish space. 10 minute walk to History! 15 minute walk to the beach! Complete with kitchenette, 3 piece bathroom, and an upstairs bedloft (watch your head - 5'3"). There's a queen bed upstairs and a Spaze pullout sofabed downstairs. Rounding out the space is a TV, highspeed internet, and a minisplit ductless AC/heat pump. Linens and towels are provided. Please note steep stairs and low headroom in the loft. Operator Registration STR-2109-FMGHHC.

Private Coach House near the Bluffs
This separate, minimalist, self-contained coach house is a perfect quiet escape for one, and can also intimately accommodate two persons. Wake up in natural light with all the essential home comforts: a premium queen-size mattress, hypoallergenic, 100% cotton linens, a separate bathroom, toiletries and kitchen basics. Nearby options for prepared meals, groceries + delivery. No TV. No extra housekeeping fees. A 20-minute getaway from the downtown core near the lake in the east end.

Newly renovated & contemporary 2 Bdrm Basement Apt
Welcome to our newly renovated spacious 2 bedroom, 1 bathroom basement apartment with a full kitchen. Unlimited and strong high-speed Wi-Fi. We have a flat screen TV with Google Chromecast so that you can view and stream from your smartphone/laptop. Close to LCBO (5 minute walk), NoFrills (5 minute walk) and Pearson Airport (15-20 mins drive). The property is located in the borderline between Brampton and Mississauga on the intersection of Steeles Avenue & Mavis Road.

Zorro Guest Suite • Central, Cozy & Private
Newly built cozy attached guest suite w/ private entrance. On a cul-de-sac in a quiet area, yet centrally located. Acoustically insulated for a quiet nights sleep. * 15/20 minutes to YYZ Airport & 5 minutes to Square One shopping center. * 30 minute drive to Toronto * 1 hr drive to Niagara Falls. * Ideal for traveling couples or a solo professional. * Garden views from indoors and from a designated outdoor patio space. * 1 parking spot available in our driveway.

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.
Popular amenities for Pickering guesthouse rentals
Family-friendly guest house rentals

Bright & Cozy Studio w/ Private Entrance & Parking

Cozy 2 Bedroom Peacful Family Getaway!

Incredible summer2025 sale Lux. fully private unit

Cozy guest unit

Adorable 2-Bedroom Quiet Neighbourhood Renovated

Trinity Bellwoods Newly Renovated Guest Suite

Chic & Cozy: Renovated Studio

Newly Renovated, Relaxing Getaway
Guest house rentals with a patio

Guesthouse w/ HOT TUB mins from Subway & Danforth

The Farmhand’s Cottage

Adorable GH in beautiful Claremont/scenic view

Junction Private Laneway Suite with Backyard

Cottage Vibe Private Guesthouse @ Queen West

Luxury 1BD Suite/A+ Location!

The Country Guest House

Frenchman Bay Luxury Basement
Guest house rentals with a washer and dryer

Newly Constructed Downtown Brampton Garden Suite

2 bedroom Guest house in North of Toronto

Bright and Airy Guest Suite with Pool

Peace Lodge

My Happy Place - Beaches Apartment

Spacious & Bright 1Bdr Private Walkout Basement

Cozy Guest House

Luxury 2 Bedroom 2 Washroom Legal basement Apart
Quick stats about guesthouse rentals in Pickering
Total rentals
10 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
370 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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