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Guesthouse vacation rentals in Pickering

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Pickering guesthouse rentals

Family-friendly guest house rentals

Guest favorite
A modern exterior is displayed, featuring a streamlined shape with large windows. The snow-covered surroundings enhance the inviting entrance, providing access to the private space within. A bright winter's day casts natural light across the facade, emphasizing the architectural design.
Private room in Little Portugal
4.95 out of 5 average rating, 38 reviews

Private Guesthouse with Sauna

MichaelRating, 5 stars2 weeks ago
Shelley was an extremely friendly and informative host. She was always quick to respond to messages and recommended one of the best pizza places I’ve ever been to in my life that I most likely wouldn’t have found on my own. The space was a bit small for 2 but it worked out great for my wife and I. The location is top notch. My wife and I walked over 25 miles of Toronto and the area Shelley’s place was located was easily the most fun and interesting area we had explored. You can literally NOT find a better place for restaurants and cocktail bars. Every single restaurant and cocktail bar we went in was top notch and VERY easy to walk to. I highly recommend this space if you’re looking to save some money on the place you want to shower and sleep and would rather spend that money on food and beverage.
A spacious bedroom features a queen bed with a quilted cover and decorative pillow. A bedside table with a lamp provides soft lighting. Natural light filters through a window with blinds, illuminating the wooden flooring and warm wood-paneled accent wall.
Private room in Markham
4.82 out of 5 average rating, 74 reviews

friendly house

TomRating, 5 stars64 months ago
Very friendly, even helped me find my keys. I will stay there again.
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, 196 reviews

Self Contained Luxury Studio Coach House

ZsofiaRating, 5 stars1 week ago
We feel truly lucky to have stayed at this wonderful Airbnb. Rohan was an exceptional host – incredibly helpful, kind, and welcoming. From the moment we arrived, we felt completely at home. The apartment was beautifully equipped with everything we could possibly need – and even more! The neighborhood is lovely, peaceful, and conveniently located with everything close by. We genuinely couldn’t have asked for a better stay. We wholeheartedly recommend this place and would come back again in a heartbeat.
Guest favorite
A spacious studio suite is presented, featuring a large bed positioned against a wooden headboard. Soft lighting illuminates the room, which includes a kitchenette and a small dining area visible in the background.
Guesthouse in Trinity-Bellwoods
4.92 out of 5 average rating, 155 reviews

Cozy & Bright Private Suite in Trinity Bellwoods

LizRating, 5 stars2 days ago
Absolutely amazing place Amanda has, the location right next to Bellwoods park is just perfect for those warm evenings. Amanda was an amazing host who gave some really good recommendations for what to do in the Toronto area. Will definitely book again when i’m back in Toronto!
Top guest favorite
A well-maintained front yard features an array of colorful flowers, including yellow and purple blooms, alongside lush greenery. A pathway made of stone leads toward the entrance of the house, with landscaping lights lining the way. A decorative pot with a plant adds a charming touch.
Guesthouse in Toronto
4.93 out of 5 average rating, 313 reviews

Free Parking 2BD Queen St. East

MitchRating, 5 stars1 month ago
I had a truly wonderful stay at Branko, Milan, and Bissa’s place, conveniently located in the east end of Toronto. From the moment I arrived, Bissa and Milan made me feel incredibly welcome—like part of the family! They were a joy to chat with whenever our paths crossed, and Branko was always quick and helpful with any questions before and during my stay. The hosts live in the main and basement floors and the second and third floors, accessed through a private entrance, offered more space than expected. It was peaceful, quiet, and perfect for rest after long days. Decorated with plenty of interesting artwork for all tastes. The dedicated parking spot was a huge plus, and I appreciated the hot showers, cozy bedding, soft towels, and fully equipped kitchen and bathroom—everything I needed for a 6-week stay. I’m already looking forward to my next project in Toronto, as their place is high on my list. I would absolutely stay again!
Superhost
A modern living area showcases minimalist furnishings, including two dark armchairs facing a sleek coffee table. The wall features a large mirror and built-in shelves adorned with decorative items. Soft lighting illuminates the space, with a patterned rug resting on hardwood floors.
Guesthouse in Bronte
4.6 out of 5 average rating, 10 reviews

*Cozy&Chic LL 2Bed 2Bath-Kitchenette l *Near LAKE*

JulieRating, 5 stars4 months ago
A truly intimate and comfortable internet spot perfect for a vacation

Guest house rentals with a patio

Guest favorite
A spacious sleeping area features a queen size bed, framed by soft drapes and decorative pillows. A cozy chair sits near a small table on a patterned rug, while artwork adorns the walls, creating a calming environment.
Guesthouse in Erin Mills
4.95 out of 5 average rating, 101 reviews

Cozy & stylish basement apartment in Mississauga

AnneRating, 5 stars3 weeks ago
Very reasonable price. Park across the street and a good ice cream shop within 10 minute walk.
Superhost
A cozy living area is furnished with a light-colored sofa and a wooden coffee table centered on a soft rug. A large mirror is mounted on a wooden wall unit, which features cabinets for storage. Bright lighting enhances the warm tones of the wooden flooring.
Guesthouse in Pickering
5 out of 5 average rating, 4 reviews

Romantic Private Guest House

KunalRating, 5 stars4 months ago
Lovely place to stay, clean, comfortable and well equipped, it looks exactly what the images shows and had everything we needed. Saulmaz is really a great host and we really enjoyed our stay here. Would definitely Consider returning to this property for a long stay.
Guest favorite
The kitchen features modern appliances, including a stainless-steel refrigerator and a gas stove. A round table with two chairs is positioned in the space. Decorative elements include a small indoor plant and an overhead light fixture that enhances the room's functionality.
Guesthouse in CA
4.92 out of 5 average rating, 24 reviews

Adorable GH in beautiful Claremont/scenic view

StephanieRating, 5 stars4 weeks ago
What a wonderful place! They had everything I needed, and it was so lovely and charming. It really felt like home! Plus, it’s conveniently close to all the surrounding towns.
Top guest favorite
The image captures a serene lake at sunset, reflecting vibrant hues of orange and purple in the sky and water. A wooden dock extends into the calm water, providing a tranquil setting for evening activities.
Guesthouse in Port Perry
5 out of 5 average rating, 84 reviews

Lakeside Guest Suite, on Lake Scugog, Port Perry

AnureetpalRating, 5 stars1 day ago
We had a really good time, the place is spotless and very cozy. It’s accommodated with everything. The view is beautiful and peaceful. Lydia and Craig are very responsive, friendly and respectful. 10/10 experience and grateful for snacks/haply birthday sign/ carved gift during welcome.
Guest favorite
A spacious bedroom features a comfortable bed with a patterned blue throw blanket and decorative pillows. Two windows provide natural light, while a minimalist bench is positioned at the foot of the bed. Artwork adorns the wall above the bed, enhancing the room's decor.
Guesthouse in Stockyards District
5 out of 5 average rating, 26 reviews

Junction Private Laneway Suite with Backyard

JessieRating, 5 stars4 weeks ago
Without exaggerating, this is one of the best Airbnbs I've stayed in in Canada. The space was super clean, had no perfume, and there were no bad smells. The linens were clean and smelled very good. The space was even better in real life than in the photo. I loved the concept, the decor and especially the location which is right next to a mall, several restaurants and public transport. The host was available and very responsive. Thank you so much 🙏🏾
Guest favorite
The open living space features wooden beams and a cozy sleeping area with a patterned bedspread. A dining table is set with plates and utensils, while two upholstered chairs are arranged nearby. Light is provided by ceiling fixtures, enhancing the bright atmosphere.
Guesthouse in North York
4.97 out of 5 average rating, 31 reviews

Luxury 1BD Suite/A+ Location!

DimitriRating, 5 stars2 weeks ago
Spotless, everything set up to make my stay as trouble free as possible. I especially liked the availability of travel toothbrushes, shaving foam, razors and assorted toiletries. Bright white towels were a nice touch as well. Welcome chocolates, chips and sweet crackers available also. As for the property, ideally located , quiet, beautiful garden with a number of lush green maple trees providing a memorable morning view. Assigned parking in front of the unit. One would be hard pressed to find better for the price in Toronto.
Guest favorite
A modern basement living space features an open layout with a spacious kitchen island, equipped with stylish bar stools. A comfortable seating area is visible, accented by a warm-toned sofa and decorative coffee table. Bright lighting enhances the contemporary design, with oversized windows providing natural light.
Guesthouse in Pickering
4.96 out of 5 average rating, 25 reviews

Frenchman Bay Luxury Basement

AaronRating, 5 stars1 day ago
Huma was so kind and friendly; her warmth made us feel like we were staying with family. The apartment is exceptionally comfortable and clean, with a very nice layout and thoughtful design. The home is easy to access from the highway and located in an ideal spot for exploring the waterfront trails. We enjoyed the bbq and outdoor space, but most of all we appreciated Huma’s amazing hospitality. Thank you, Huma! See you next time! ❤️
Superhost
A bright living space features a large wall-mounted TV above a wooden console. A cozy sofa with soft throws faces two plush chairs. Green plants add a touch of nature, while a light rug ties the seating area together, creating a welcoming atmosphere.
Guesthouse in Midtown
4.91 out of 5 average rating, 22 reviews

Downtown Toronto Urban Retreat!

DerekRating, 5 stars1 month ago
It was a pleasant 3 month stay for me and my wife. Very quiet and scenic, and hosts (Jeff and Jessica) were very kind in accomodating to our needs. Highly recommend!

Guest house rentals with a washer and dryer

Guest favorite
A jetted hot tub is surrounded by a privacy screen, emitting soft glow from multicolored LED lights. Steam rises from the water, creating a serene atmosphere ideal for relaxation under the stars.
Guesthouse in East Danforth
4.94 out of 5 average rating, 35 reviews

Guesthouse w/ HOT TUB mins from Subway & Danforth

GailRating, 5 stars1 month ago
Amazing oasis in the city. Nice to have a hot tub after a long day. I just loved every minute of my stay!!! There was ice cubes in the freezer and a great booklet with everything you need to know! Oh and a Kuerig machine for coffee. that's a nice touch.
Guest favorite
The entrance to the apartment is marked by a sleek, black front door set against a warm wood panel exterior. A pathway lined with landscaping leads to the door, with green grass and small flowering plants enhancing the inviting approach.
Guesthouse in Toronto
4.96 out of 5 average rating, 67 reviews

Newly Built, One-Bedroom Stylish Apartment

DavidRating, 5 stars10 months ago
We loved everything about staying at Laura’s. She was a great host and very responsive and attentive. We did not need for anything during our stay. We can’t wait to stay here again!
Guest favorite
A modern living space features a comfortable sofa with decorative pillows. A small dining area with a table is positioned next to a stylish kitchenette equipped with appliances. A television is mounted on the wall, and a plant adds a touch of greenery to the setting.
Guesthouse in Aurora
4.91 out of 5 average rating, 23 reviews

Delightful One-Bedroom Unit Aurora W/ free Parking

YuRating, 5 stars2 weeks ago
If you are visiting Aurora or even northern Markham / Richman hill, this is a great spot to stay. Very clean, quiet and close to everything. Hooman is very nice to communicate with, made everything go smoothly.
Guest favorite
A teal side table displays two framed artworks. On the left, a light-colored image captures soft blue tones, while the right features a vibrant green cactus illustration in a black frame, creating a serene and stylish corner.
Guesthouse in Garden District
4.87 out of 5 average rating, 86 reviews

Downtown - 1 Bedroom Home, Upper unit of house

JonieRating, 5 stars5 days ago
Deborah’s place was exactly as described. Very clean and quiet. Would definitely stay here again when in Toronto.
Guest favorite
A countertop is displayed with various kitchen tools and utensils, including a modern pot and pan set, a kettle, and a selection of cutlery and glassware. A cookbook titled 'Crazy Sweet Creations' lies open, showcasing culinary inspiration.
Guesthouse in Newmarket
4.8 out of 5 average rating, 20 reviews

Tranquil Spacious Unit

JulieRating, 5 stars3 days ago
I really enjoyed my stay it was nice and quiet and a good area lots of stores around I would definitely stay here again and recommend it and the price is right.
Superhost
A functional kitchen features modern appliances, including a refrigerator and a combination washer and dryer. The room is designed with light cabinetry and wooden flooring, creating a spacious atmosphere. A small countertop and a microwave complete the cooking area, with a trash bin positioned in the corner.
Guesthouse in Markham
4.74 out of 5 average rating, 74 reviews

The Cozy Apartment Style Home

WeihongRating, 5 stars3 months ago
Kiano and Merry are extremely friendly and responsive hosts. There had been snow storms and a temporary power outage in the area during our stay, they kept us posted on the updates, always made sure the pathways that we would use were ice- and snow-free. The neighborhood is peaceful and friendly.
Superhost
A kitchen drawer is open, revealing a selection of cooking utensils and tools. Items include a ladle, spatula, grater, and brush, all organized neatly within the white drawer. The smooth surface of the countertop and modern appliances are visible in the background.
Guesthouse in Richmond Hill
4.8 out of 5 average rating, 15 reviews

Charming 1BR Apt with Private Entrance & Parking

CristinaRating, 5 stars1 month ago
Nojan was very helpful and responsive. Upstairs can be a bit noisy, but overall a great place to stay. Thank you for everything!
Top guest favorite
A modern kitchen is equipped with stainless steel appliances, sleek cabinetry, and a spacious countertop. A window allows natural light to fill the space, while a coffee maker and toaster are positioned beside the sink. A pop of color is introduced with a red mat under the sink.
Guesthouse in Richmond Hill
4.91 out of 5 average rating, 32 reviews

Complete 2 bedroom Separate Apartment

MarkRating, 5 stars4 days ago
Massoud helped me any time that i need something. thank you for your great hospitality!

Quick stats about guesthouse rentals in Pickering

  • Total rentals

    20 properties

  • Nightly prices starting at

    G$6,295 GYD before taxes and fees

  • Total number of reviews

    460 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

Destinations to explore