Guesthouse vacation rentals in Pickering

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Top-rated guesthouse rentals in Pickering

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A stately two-story brick house features a symmetrical facade, highlighted by tall arched windows and a prominent entrance. Lush green landscaping surrounds the property, including well-maintained shrubs and trees, set against a clear blue sky.

Guesthouse in CA

4.91 out of 5 average rating, 23 reviews

Adorable GH in beautiful Claremont/scenic view

Take it easy at this unique & tranquil getaway, located in Claremont, ONT. Enjoy privacy, while only 45mins from Downtown Toronto. Central to Markham, Stouffville, Uxbridge, Ajax, Whitby & surrounding areas. 10 Minutes to 407, 17mins to 401. Full kitchen, washroom, upper level bedroom, patio (bbq), laundry etc. Winter ice rink in backyard. Fully contained unit. Transportation: To/From Airport To/From Toronto DT Not included in price, msg to inquire 5 Mins to Country Restaurant See house rules⁹

Guest favorite

An open studio layout displays a cozy sleeping area alongside a well-equipped kitchen. Light grey walls enhance the space, while two bedside lamps provide soft illumination. In-suite laundry is visible next to the kitchen, and a welcoming couch adds comfort to the environment.

Guesthouse in Oakville

4.93 out of 5 average rating, 195 reviews

Self Contained Luxury Studio Coach House

Your Perfect Home Away from Home! This immaculate, private studio with a separate entrance is designed for comfort and convenience. Nestled in a peaceful suburb yet centrally located near major highways, it offers walking access to restaurants, grocery stores, and a park. Thoughtfully furnished, it’s cozy in winter, cool in summer, and fully equipped for a hassle-free stay. Guests love the warm ambiance, calling it a truly special experience. Come see why our coach house is the perfect getaway!

Top guest favorite

Cupboards are opened to reveal organized dishware, including plates, bowls, and glasses. A clean and modern aesthetic is presented, complemented by stainless steel appliances visible nearby. The surfaces feature a geometric tile design, enhancing the kitchen's functional layout.

Guesthouse in Whitby

4.97 out of 5 average rating, 176 reviews

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.

Guest favorite

An aerial view of a modern staircase leads to a lofted sleeping area with a queen bed. Natural light filters through flowing curtains, illuminating a live edge walnut table and a stool. Open shelving displays decorative items, enhancing the cozy ambiance of the compact space.

Guesthouse in Aurora

4.91 out of 5 average rating, 146 reviews

Adorable Guesthouse Apartment With Free Parking

This beautiful brand new suite offers, Separate private guesthouse with vaulted ceilings & heated floors throughout. Private bathroom with standing shower. Queen loft bed & pull out couch. Flat screen smart TV. Kitchenette which includes: Fridge, cooktop & cookware, toaster oven, kettle, coffee maker. Live edge walnut table with 2 stools. Free wifi. 1 Free parking space. Close to Go Train. Fresh bed sheets & towels are provided. Phone charger and blue tooth speaker. Instagram @blueheronloft

Guest favorite

The inviting living area features warm wood accents and a cozy seating arrangement. A brick fireplace stands as a focal point, complemented by large windows that flood the space with natural light. Ferns add a touch of greenery, enhancing the relaxing atmosphere.

Guesthouse in Uxbridge

4.96 out of 5 average rating, 136 reviews

Guesthouse in nature mins to Ski hills and 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!

Guest favorite

A modern bathroom is presented, featuring a freestanding white bathtub complemented by a glass shower enclosure. Large windows provide natural light to the space, which is adorned with elegant marble walls and a patterned floor tile, enhancing the contemporary design.

Guesthouse in Richmond Hill

4.97 out of 5 average rating, 137 reviews

Balcony House with Separate Entrance, 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 parkings

Guest favorite

A well-equipped kitchen features modern stainless steel appliances, including a refrigerator and oven. A small dining table with two chairs is positioned near a large window, allowing natural light to fill the space. The room has a neutral color palette, enhancing its airy atmosphere.

Guesthouse in Richmond Hill

4.94 out of 5 average rating, 115 reviews

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 free parking.

Guest favorite

A wooden bench is positioned along a sandy beach, framed by lush green foliage. The calm blue waters extend towards the horizon, with scattered rocks along the shore. A lifeguard stand is visible in the distance, under a partly cloudy sky.

Guesthouse in Toronto

4.97 out of 5 average rating, 143 reviews

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.

Superhost

The modern entrance of a high-rise building is showcased, featuring a sweeping canopy that extends over a circular drive. Floor-to-ceiling windows allow for ample natural light, and guests are seen approaching the entrance, with parked vehicles nearby.

Guesthouse in Pickering

4.83 out of 5 average rating, 139 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!

Guest favorite

A natural pathway meanders through a vibrant garden, flanked by lush greenery and blooming flowers. Birch trees provide shade alongside the path, leading to a wooden bridge nestled among various plant life. Soft sunlight filters through the foliage, creating a serene atmosphere.

Guesthouse in Scarborough

4.96 out of 5 average rating, 116 reviews

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.

Guest favorite

A secluded cabin is illuminated warmly against a dark skyline, surrounded by lush trees. The solar panel is visible beside the cabin, and a clear view of the starry sky adds to the serene atmosphere. The surrounding grass reflects the soft glow of the cabin's light.

Guesthouse in Newcastle

4.88 out of 5 average rating, 195 reviews

Bee Keeper's Cabin - a very private retreat

91 acres, trails, total privacy, spring fed lake, solar power/propane heated, gas stove top, propane fridge, out-house, firepit, wi-fi ; canoe/paddleboat (seasonally) Self check in and self cleaning For those who leave a "light foot print" Basic kitchen utensils, pots, pans, and dishes are provided, BUT guests must bring their own drinking water, pillows and bedding. We ask our guests to leave the cabin better than you found it and to take all garbage and recycling home with you."

Guest favorite

A kitchen drawer is open, revealing a neatly organized assortment of utensils, including cutlery and kitchen tools. Below, a second drawer holds a set of dishes, including bowls and plates. A gray oven mitt rests beside the drawer on the countertop.

Guesthouse in Scarborough

4.9 out of 5 average rating, 21 reviews

City Guesthouse by the Lake Feels Like Home

This special place is close to everything, making it easy to plan your visit. Bright Basement Guesthouse Home Away From Home - Walk to Lake Ontario , Beach, Walking Trails - Free parking on street - Scarborough Bluffs - Neighbouhood Park with Splash Pad for the kids - Rosetta Gardens, The Guild Inn - Scarborough Village Theatre - Scarborough Town Centre shopping - 30 min drive to Downtown, CN Tower, World-class restaurants, shopping - 2 hour drive to Niagara Falls