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 wooden deck is adorned with vibrant flowers in various colors, offering a lush garden view. A table set with chairs and an umbrella is visible, surrounded by greenery, creating a serene outdoor space ideal for relaxation or dining.

Guesthouse in Toronto

4.93 out of 5 average rating, 108 reviews

Very clean; prime location; breakfast

DavidRating, 5 stars2 weeks ago

The host is very friendly and welcoming. A good selection of basics are provided for breakfast/lunch, including milk, tea, oats, cornflakes, Nespresso, bread, etc. The toilet includes a convenient bidet attachment. Tall visitors will have to watch out for low ceilings in places. Note that the heating vents in the bedroom can be closed if desired. The Himalayan Coffee house nearby is excellent.

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

JennicaRating, 5 stars2 weeks ago

My family and I really enjoyed staying here. The place was compact but was enough space for the three of us. There were plenty of towels and everything was very comfortable. Instructions were easy to follow and Shu was very accommodating and responsive to any needs we had. Would definitely book this place again if I’m in Richmond Hill

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

MichaelRating, 5 stars4 days ago

Second stay with Duncan, and it was excellent. Felt so nice being somewhere familiar and comfortable. Happened to bump into him this time too, and he's as nice in person as he seems in message. Spotless, cozy, and everything you need right in an adorable lil home, in a quiet neighborhood that's right next door to lots of fun. Also, that bed is pretty darn comfy. Only thing better than the first stay are the ones after, Duncan knows how to treat a returning customer and I'm definitely coming back again. Thanks for everything!

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

TayyabaRating, 5 stars4 months ago

Great host and a great location! Georgia was easy to communicate with. This place is close to the mall, and lots of restaurants. The rooms are quite spacious and have a tv in each room which was a nice addition. Kids had toys to play with as well. Overall we had a great time.

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

SarahRating, 5 stars1 month ago

This is my dream home, so I was really sad to leave. It's like a modern cabin but in the city. It's exactly what I needed; a clean, quiet, safe place to regulate my nervous system. Toni was great and thought of everything and left detailed instructions, high-quality supplies and did the linens every week. The bed is really nice compared to other airbnbs and hotels. I also loved how it was never cold, which is another issue I've had with places in the past. The hot water here is very hot, which I am a big fan of. I stayed here for a month and was able to make it work without a full fridge or kitchen. I really hope I get to stay here again.

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Popular amenities for Pickering guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guest favorite

Private room in Little Portugal

4.93 out of 5 average rating, 30 reviews

Private Guesthouse with Sauna

DarylRating, 5 stars1 month ago

It was an amazing stay. The location was quiet and peaceful yet close to everything I needed. The bed was truly, amazingly comfortable! Shelley was a gracious, friendly and helpful host.

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

4.91 out of 5 average rating, 151 reviews

Cozy & Bright Private Suite in Trinity Bellwoods

KaseyRating, 5 stars2 weeks ago

A wonderful stay away from home! For being such a central and bustling neighbourhood, Amanda’s spot was extremely quiet and private which was just what we needed. Thanks for everything!

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 West

4.6 out of 5 average rating, 10 reviews

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

JulieRating, 5 stars3 months ago

A truly intimate and comfortable internet spot perfect for a vacation

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 stars63 months ago

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

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Guest house rentals with a patio

Guest favorite

A modern kitchen area features white cabinetry and a stone countertop. Included are a stainless steel refrigerator, a microwave, and a cooktop with a hood. A washer and dryer are visible, along with a wooden dining table and chairs positioned nearby.

Guesthouse in East Danforth

4.94 out of 5 average rating, 34 reviews

Guesthouse w/ HOT TUB mins from Subway & Danforth

GailRating, 5 stars1 week 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 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

5 out of 5 average rating, 29 reviews

Luxury 1BD Suite/A+ Location!

JuneRating, 5 stars6 months ago

Amazing place! Perfect location for my first time in Canada as there were lots of bus stops nearby to easily get anywhere in the city without a car. The place itself was great. Very spacious and looked just like the photos. Perfect for late mornings or nights in, with the tv and kitchen table for when we didnt eat out. The bed was also big and didn’t feel like we were being squished together trying to fit. Would stay here again if it’s available during my next trip to toronto!

Guest favorite

An outdoor patio area features a barbecue grill under a sheltered counter. White wooden chairs with red cushions are arranged around a small round table, creating a relaxing space for dining or socializing. The paved surface and surrounding greenery add to the inviting atmosphere.

Guesthouse in Pickering

4.95 out of 5 average rating, 21 reviews

Frenchman Bay Luxury Basement

QuinntinRating, 5 stars2 weeks ago

We absolutely loved staying at Huma’s place. She was a very friendly and welcoming host and the place was comfy, clean, and had everything we needed. Will definitely be staying again next time we’re in the area!

Guest favorite

Guesthouse in Aurora

4.91 out of 5 average rating, 22 reviews

Delightful One-Bedroom Unit Aurora W/ free Parking

AvivRating, 5 stars5 days ago

Very tidy, well set up, and cozy, great location. Loved the stay!

Superhost

Guesthouse in Midtown

4.9 out of 5 average rating, 21 reviews

Downtown Toronto Urban Retreat!

NancyRating, 5 stars4 months ago

Location was great. Near TTC but quiet.

Guest favorite

A well-lit living area features a large flat-screen TV mounted above a brick fireplace. A wooden coffee table rests on a soft area rug, accompanied by a dark dresser and a mirror reflecting the space. An entrance to the kitchen is visible in the background.

Guesthouse in Rexdale

4.95 out of 5 average rating, 22 reviews

Private Guest Suite in Toronto

SukanyaRating, 5 stars2 weeks ago

I had a wonderful stay at Rabita’s place! The space was exactly as described, clean, cozy, and thoughtfully arranged. The location was convenient and peaceful, making it easy to relax after a long day. Rabita was an attentive and responsive host, always available if I had any questions. I’d definitely recommend this listing to anyone looking for a comfortable and hassle-free stay. Would love to come back!

Guest favorite

Guesthouse in Pickering

4.92 out of 5 average rating, 98 reviews

Cozy Cabin w/ Private Hot tub & Firepit

AmandaRating, 5 stars1 month ago

Lovely quiet retreat and Adrienne was very responsive. We had a great time and hope to return soon!

Guest favorite

A spacious bedroom features a large, upholstered bed with a light-colored headboard and decorative pillows. Nightstands with lamps are positioned on either side. A world map artwork hangs above the bed, and soft towels are neatly rolled on the blanket.

Guesthouse in Pickering

4.93 out of 5 average rating, 27 reviews

Spacious fully private studio basement & parking

HariRating, 5 stars4 months ago

Soulmaz’s place is one of the best in town in a safest neighborhood which makes you feel at home. This little studio with adequate space is a perfect place to unwind and spend your time in peace. If you are looking for a home away from home with all amenities to stay, you will definitely enjoy this place. What stands out in this unit is the carefully thought out personalization for any traveller or tourist who wants to relax and settle down. I wish I could have stayed longer and enjoyed the quiet and great atmosphere around this place. I am definitely staying here the next time when I am in this part of town. Thanks Soulmaz for the warm welcome and comfortable place!

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Guest house rentals with a washer and dryer

Guest favorite

A modern kitchen space features sleek white cabinetry and stainless steel appliances, including a refrigerator, oven, and dishwasher. A microwave is mounted above the stove, and open shelving displays decorative items. Warm wood flooring complements the overall design.

Guesthouse in Markham

4.87 out of 5 average rating, 46 reviews

2 bedroom Guest house in North of Toronto

StuartRating, 5 stars2 weeks ago

Felt right at home, would not hesitate to book again

Top guest favorite

A narrow studio layout showcases natural light flowing through windows, illuminating the cozy bed with crisp white bedding. A mirror reflects the space, and a gray sofa with striped accents provides a comfortable seating area. A private entrance is visible, enhancing accessibility.

Guesthouse in Richmond Hill

4.97 out of 5 average rating, 70 reviews

"Modern Urban Studio Retreat"

HelenRating, 5 stars4 days ago

Small yet cozy setup. Enjoyed the stay very much!

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 stars8 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!

Top guest favorite

A modern kitchen featuring sleek white cabinetry and stainless steel appliances. A spacious island is complemented by bright yellow bar stools. Natural light enters through a window, illuminating the countertops and creating a clean, inviting space for meal preparation.

Guesthouse in Newmarket

5 out of 5 average rating, 72 reviews

Fairytale - Spotlessly Clean Getaway - 2 Bedroom

AliciaRating, 5 stars3 months ago

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!

Superhost

A spacious living area is highlighted by a comfortable queen-size bed with white linens. A cozy fireplace is framed by a brick mantle, and a kitchenette area is visible in the background, featuring modern appliances and a dining table with chairs.

Guesthouse in Richmond Hill

5 out of 5 average rating, 3 reviews

Charming Cozy Studio w/ Private Entrance & Parking

RudiRating, 5 stars1 month ago

Really enjoyed my stay, clean and friendly service. Woyld definitely book here again.

Guest favorite

A modern kitchen counter displays an electric toaster oven and an induction cooktop. Two drawers are open, revealing kitchen utensils, including measuring cups, a grater, and various cooking tools, organized neatly for easy access.

Guesthouse in Richmond Hill

5 out of 5 average rating, 5 reviews

Cozy Studio with Private Entrance & Parking

VictoriaRating, 5 stars2 months ago

Quiet and safe neighbourhood about 35 minutes from city centre with a nice walking path around a pond nearby. Lots of really good restaurants and grocery nearby. Medium sized fenced in yard great for dogs. Clearly marked smoking area. Large driveway spot for car fits SUV. Place was exactly what you expect from the photos - small, but it’s enough space for one person. Host is extremely responsive and helpful. Recommended if you are looking for hassle-free! Tip: there are no bedsheets provided so bring your own double sized. Great stay. Thank you!

Guest favorite

A modern living area features a spacious gray sectional sofa and a sleek black coffee table. A dining table for four is positioned nearby, with a minimalist kitchen equipped with stainless steel appliances visible in the background. Soft lighting adds to the welcoming ambiance.

Guesthouse in Richmond Hill

4.9 out of 5 average rating, 10 reviews

Elegant 1BR Apartment w/Private Entrance & Parking

JulannRating, 5 stars1 week ago

Wonderful place to stay. A walk up the street will find you looking at a barn. Very tranquil considering how busy it can be. Space was warm and clean. Highly recommend.

Superhost