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

Private Guesthouse with Sauna
Everything in this carefully designed duplex coach house is just so. Unlocking the European-style tilt & turn outer door maybe a challenge at first, but it works well. Two large non-representational paintings are pleasing dashes of colour in the main studio bedroom. The loft sauna is very cleverly designed and easy to use. The passageway to access the backyard and the suite is as little as 22-inches wide at a couple of points, which may be difficult for some people and luggage to traverse. But it's worth the squeeze!

friendly house
Very friendly, even helped me find my keys. I will stay there again.

Self Contained Luxury Studio Coach House
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.

Cozy & Bright Private Suite in Trinity Bellwoods
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!

Free Parking 2BD Queen St. East
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!

*Cozy&Chic LL 2Bed 2Bath-Kitchenette l *Near LAKE*
A truly intimate and comfortable internet spot perfect for a vacation
Guest house rentals with a patio

Cozy & stylish basement apartment in Mississauga
The most stylish Airbnb we’ve stayed at so far! This unique styled interior was so luxurious to stay in! The amenities were fantastic. Everything you need and more! We are traveling at the moment so this was nothing but perfect for us!! The bed was sooo comfy! Best night sleep! Amazing space! Very spacious! Helpful suggestions were left on things to do around the area which was much appreciated! Couldn’t recommend this place anymore! Thank you for having us 😊

Romantic Private Guest House
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.

Adorable GH in beautiful Claremont/scenic view
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.

Junction Private Laneway Suite with Backyard
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 🙏🏾

Lakeside Guest Suite, on Lake Scugog, Port Perry
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.

Luxury 1BD Suite/A+ Location!
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.

Frenchman Bay Luxury Basement
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! ❤️

Private Guest Suite in Toronto
Great spot for a single person or couple that wants to see and do things in Toronto, but prefer somewhere more quiet and residential to retire at night. The price for a weekend stay was very reasonable. Thank You.
Guest house rentals with a washer and dryer

Guesthouse w/ HOT TUB mins from Subway & Danforth
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.

Newly Built, One-Bedroom Stylish Apartment
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!

Fairytale - Spotlessly Clean Getaway - 2 Bedroom
You will not regret staying here! I spent 6 weeks here while waiting to move into my own place and I really didn't want to leave. place was spotless, inside and out; it's everything described and more! Alex and his wife are lovely people, he responds almost immediately, very accommodating, and helpful! will definitely be staying here again whenever I visit ontario! Thank you Alex for making me feel at home!

Delightful One-Bedroom Unit Aurora W/ free Parking
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.

Cozy Private Entire Basement 1 Bedroom & 1 Bath
Oke was an exceptional host and had a wonderful home! Would stay again!

Downtown Toronto Urban Retreat!
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!

Tranquil Spacious Unit
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.

The Cozy Apartment Style Home
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.
Quick stats about guesthouse rentals in Pickering
Total rentals
20 properties
Nightly prices starting at
G$6,276 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
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- Massey Hall
- BMO Field
- Trinity Bellwoods Park
- Casa Loma
- Jackson-Triggs Niagara Estate
- Royal Woodbine Golf Club
- Dufferin Grove Park
- Royal Ontario Museum
- Hockey Hall of Fame
- Cobourg Beach