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Guesthouse holiday rentals in Greater Toronto and Hamilton Area

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Greater Toronto and Hamilton Area guesthouses

Family-Friendly guesthouses

Guest favourite
Guesthouse in Saint Anns
4.98 out of 5 average rating, 191 reviews

The Carriage House @ Mingle Hill

StuartRating, 5 stars5 months ago
I am an owner of a B&B and this spot is the best place I’ve stayed. Emily and Randy are phenomenal hosts!!! The space has everything you could think of including a first aid kit and Tylenol which comes in handy in wine country. The down pillows were very comfy and so was the bed. The bathroom area has a heat lamp to keep you extra warm after a shower. The place has beautiful curated antiques and lovely lavender products from the lavender farm. The farm fresh eggs and bacon add to the whole experience. The hosts have a beautiful store that sells amazing lavender products from their farm. We walked the grounds also which were very a great example of all of Emily’s and Randy’s hard work!
Guest favourite
Guesthouse in Oakville
4.93 out of 5 average rating, 195 reviews

Self Contained Luxury Studio Coach House

SamuelRating, 5 stars4 months ago
The place is great. Well situated and very clean. Very private and the hosts we very welcoming.
Guest favourite
Guesthouse in Schomberg
4.93 out of 5 average rating, 423 reviews

Country Cabin Escape | King Bed | Pet Friendly

AdaRating, 5 stars1 week ago
I spent one night at this property with two friends and had a wonderful experience. The cabin was exceptionally clean, including the washroom, and came fully equipped with all the necessary amenities. Both the kitchen and the shower had reliable hot water, which added to the comfort of our stay. The natural surroundings were peaceful and scenic, with beautiful woods and well-maintained trails that made for a perfect afternoon walk. Our host, Lisa, was welcoming and attentive, ensuring everything was in place for a smooth and enjoyable visit. This is an ideal spot for anyone looking to relax and recharge in nature. Highly recommended!
Guest favourite
Guesthouse in Waterford
4.78 out of 5 average rating, 85 reviews

14 acre forest paradise Upscale Loft with Pool

StevenRating, 5 stars6 months ago
The place was very nice, quite & peaceful area, walking trail on the property, surrounded by nature. It was very enjoyable for the time that was spent there. Very nice hosts. Would definitely rent again.
Superhost
Guesthouse in Oakville
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
Guest favourite
Guesthouse in Orangeville
4.95 out of 5 average rating, 351 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

AlexRating, 5 stars1 month ago
What a gorgeous place to get away from the city for a few days. The comfortable studio has everything you'd need during your stay. The fields are great for walking (especially if you have a dog), and there are all kinds of magnificent hiking trails nearby. My arrival coincided with a massive ice storm and Vince and Miranda were in touch every step of the way, keeping me updated on conditions and options. They were a pleasure to deal with. I look forward to returning next time I need a taste of the country.
Top Guest favourite
Guesthouse in Woodstock
4.97 out of 5 average rating, 29 reviews

Modern Country Escape

ElizabethRating, 5 stars8 months ago
I had a lovely stay at Jenne's place. It's a pristine, elegant space in tranquil surroundings, and Jenne clearly put thought into even the smallest details. She was also a very kind and responsive host. It's the perfect place to let the stress melt away. I hope to stay there again sometime!
Guest favourite
Guesthouse in Stoney Lake
4.82 out of 5 average rating, 11 reviews

Cottage suite, lakeside with beautiful view!

ShradhaRating, 5 stars2 weeks ago
Patricia & Dennis were amazing hosts and very accommodating. The loft was great with an amazing view and balcony to enjoy the weather. They were very kind and helpful. It’s a great place to enjoy and relax ..!!!

Guesthouses with a patio

Superhost
Guesthouse in Mississauga
4.82 out of 5 average rating, 49 reviews

Lovely & Cozy Apartment lots of natural light

MaherRating, 5 stars4 months ago
the place was super comfortable. looked exactly like the pictures. i loved the quality of the furniture, the bed and the couch were very comfortable, and the garden with the view was very peaceful. will come back again
Superhost
Guesthouse in Cobourg
4.88 out of 5 average rating, 17 reviews

The Wilkins - Coach House

ArleneRating, 5 stars1 month ago
Gorgeous property, the only thing I missed was a hairdryer in the bathroom. everything else was brand new and it was stunningly furnished. beautiful space to stay in.
Guest favourite
Guesthouse in Lincoln
4.96 out of 5 average rating, 113 reviews

Loft in Jordan: private balcony, close to wineries

KimberlyRating, 5 starstoday
This Airbnb was perfectly cozy and clean. It’s the perfect stay for couples visiting the area. If I visit again, I’ll for sure be staying here!
Superhost
Guesthouse in Mississauga
4.74 out of 5 average rating, 116 reviews

Luxurious Apartment overlooking Ravin & Pool

MariyamRating, 5 stars3 weeks ago
I had a great stay at Farah's place! The unit was clean and looked exactly like the photos. The host was very friendly and responsive. I would visit again!
Top Guest favourite
Guesthouse in Brantford
4.95 out of 5 average rating, 60 reviews

Zen Rustic coach house quiet private

HillaryRating, 5 stars4 weeks ago
An incredible, relaxing stay. Thank you, Marlene
Top Guest favourite
Guesthouse in Corfu
5 out of 5 average rating, 58 reviews

Miller's Meadow Your Exclusive Country Getaway!

OliverRating, 5 stars4 weeks ago
Very thoughtful and responsive host. Loved the open area behind the place. Beautiful nature and quiet. Even saw a flock of turkey!
Top Guest favourite
Guesthouse in Stratford
4.93 out of 5 average rating, 124 reviews

Brand new studio suite

MikeRating, 5 stars3 days ago
We absolutely loved our stay at Erica’s. We loved it so much we booked a second night. The place is pristine and spotless and well appointed. The outdoor space was comfortable and private. The location is walkable to downtown and in a quiet neighborhood. We are already planning our next visit.
Top Guest favourite
Guesthouse in Hamilton
5 out of 5 average rating, 55 reviews

Headwater Haven | 2 King-Beds

BarbRating, 5 stars1 week ago
I had the most lovely stay in this beautifully appointed, tasteful, sweet airbnb which was home for just two days. Serene and quiet with ultra comfortable king size beds. The proximity to trails both hiking and cycling, the gracious host and the thoughtfulness of both the decorating, extras and essentials were so sincerely noticed and appreciated. I would recommend this airbnb to anyone who wishes to explore the Niagara escarpment and stay in an elegant, centrally located carriage house/home.

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Tillsonburg
5 out of 5 average rating, 6 reviews

BosHaven Guest House

LorenaRating, 5 stars2 weeks ago
Mar’s guest house is absolutely stunning — brand new and thoughtfully designed like out of a décor magazine. Every detail felt intentional and inspiring. Mar was incredibly friendly and responsive throughout our stay. When we noticed a couple of essentials like oil and salt were missing (despite being listed), she immediately went out and picked them up for us, which we really appreciated. Highly recommend staying here — we’d absolutely come back!
Top Guest favourite
Guesthouse in Churchville
4.98 out of 5 average rating, 207 reviews

The Carriage House

KevinRating, 5 stars3 weeks ago
My wife and I had a wonderful stay at The Carriage House. Stephanie was a great host who very graciously allowed us to check in early due to an early flight. The Carriage House was cozy and we had plenty of space. The bed was comfortable and the shower, while a little tricky to figure out, had plenty of hot water. The location was perfect for our day trips to Niagara Falls, Syracuse, Salamanca, and Victor NY. We enjoyed watching the sheep and chickens on the property. The 11:00 check out time was also nice as most places we stay want you out by 9:00-10:00. We would definitely stay here again. If you stay here, be sure to eat at Stone’s Countryside Tavern. The prime rib dinner was amazing and so was the hot turkey sandwich.
Guest favourite
Guesthouse in Mississauga
4.82 out of 5 average rating, 39 reviews

Incredible summer2025 sale Lux. fully private unit

ChristyRating, 5 stars3 weeks ago
My second time staying at Zeinab and Ahmad’s. Will be back again. They are very responsive! Ahmad was wonderful about coordinating with me to have a package delivered, and on my first day I came back to the place to find Zeinab left me a care package of fruits and vegetables. I love the neighbourhood. The parking space is great! In the driveway and not complicated.
Top Guest favourite
Guesthouse in Waterloo
4.96 out of 5 average rating, 137 reviews

The Lexington Loft - A Modern & Industrial BNB

NancyRating, 5 stars1 week ago
This is our second stay at this unique property and, once again, it didn’t disappoint. This year, we had nice weather and we were able to enjoy the private patio which was an added bonus. We hope to return next year! Thanks Mikela and Mark!
Top Guest favourite
Guesthouse in East Bethany
5 out of 5 average rating, 38 reviews

Guest House in Western NY

PaulRating, 5 stars2 weeks ago
Stayed here while spending a week visiting relatives in nearby towns. Perfect stay. Definitely would come back the next time I visit the area.
Superhost
Guesthouse in Niagara Falls
4.83 out of 5 average rating, 181 reviews

bright charming 2bdrm private suite walk to Falls

TamaraRating, 5 stars4 weeks ago
This place is worth the stay! We found it so charming, plenty of space for my wife and teen daughter. We LOVED that it had a King bed for us. Lots of space in the armoire’s in each as well. Loved the rooms overall, no honest complaints! The kitchen/ dining area and attached living room, with a futon couch, was also plenty spacious for the 3 of us!! We spent a couple nights hanging out talking about our days together around the futon and living room coffee table. It was so nice to have a gathering space still. The kitchen was immaculate. Tons of plates/silverware/ cooking stuff. Felt easy to make food if you wanted to. Loved the washer/dryer but didn’t use it. The door/staircase down to the unit was a little tight with suitcases but not awful. Easy to work the door lock to get in. The door does not have a latch at the bottom, so some may feel uncomfortable, but we felt safe the whole time still! Loved this place, would definitely come back again AND recommend to others! ❤️
Top Guest favourite
Guesthouse in Mississauga
4.92 out of 5 average rating, 25 reviews

Cozy guest unit

ArsalanRating, 5 stars4 months ago
excellent hosts, very cooperative and super friendly....the basement was exactly as shown in the pictures....had a great stay here...would definitely be my 1st choice for any future Mississauga stays.
Top Guest favourite
Guesthouse in Orangeville
4.96 out of 5 average rating, 129 reviews

A bright & stylish urban studio

JuliaRating, 5 stars4 days ago
Really beautiful place within walking distance of whatever you could possibly need, responsive and helpful hosts with lots of amenities

Destinations to explore