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Guest house holiday rentals in Pickering

Find and book unique guest house rentals on Airbnb

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Popular amenities for guest house rentals in Pickering

Family-friendly guest house rentals

Guest favourite
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.
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 favourite
Guest house in Trinity-Bellwoods
4.92 out of 5 average rating, 155 reviews

Cozy & Bright Private Suite in Trinity Bellwoods

LizRating, 5 stars3 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 favourite
Guest house 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
Guest house 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 favourite
Guest house 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
Guest house 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 favourite
Guest house 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.
Guest favourite
Guest house in Stockyards District
5 out of 5 average rating, 26 reviews

Junction Private Laneway Suite with Backyard

JessieRating, 5 stars4 weeks ago
Without exaggerating , it's one of the best Airbnb I've occupied in Canada. The place was super clean had no perfume, and there was no bad smell. 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 decoration and especially the location which is right next to a Mall, several restaurants and public transportation. Host was available and very responsive. Thank you so much 🙏🏾
Top guest favourite
Guest house 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 favourite
Guest house 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 favourite
Guest house 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! ❤️
Guest favourite
Guest house in Etobicoke
4.96 out of 5 average rating, 24 reviews

Private Guest Suite in Toronto

AndreaRating, 5 stars1 month ago
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 washing machine and dryer

Guest favourite
Guest house 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 favourite
Guest house 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 favourite
Guest house in Brampton
4.92 out of 5 average rating, 37 reviews

Cozy Private Entire Basement 1 Bedroom & 1 Bath

DawnRating, 5 stars1 month ago
Fantastic stay! Can't wait to visit again.
Guest favourite
Guest house 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.
Superhost
Guest house 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 favourite
Guest house 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
Guest house in Richmond Hill
5 out of 5 average rating, 4 reviews

Charming Cozy Studio w/ Private Entrance & Parking

RudiRating, 5 stars3 months ago
Really enjoyed my stay, clean and friendly service. Woyld definitely book here again.
Superhost
Guest house in Richmond Hill
4.88 out of 5 average rating, 8 reviews

Cozy Studio with Private Entrance & Parking

IrynaRating, 5 stars1 month ago
Nojan was a great host, very responsive.

Quick stats about guest house rentals in Pickering

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹2,572 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