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Guest house holiday rentals in Caledon

Find and book unique guest house rentals on Airbnb

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Popular amenities for guest house rentals in Caledon

Family-friendly guest house rentals

Top guest favourite
Guest house in St. Catharines
4.99 out of 5 average rating, 415 reviews

Private Estate Coachhouse + Hot Tub near NOTL!

DanielRating, 5 stars1 week ago
One of the nicest AirBNB we have had the pleasure of staying at. This will definitely become a must stay during our annual trip to the Niagara Region. Just a perfect stay in a great location. Hot tub was wonderful and the cottage was super clean and stocked with everything you need ! Thanks again !
Guest favourite
Guest house 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
Guest house 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
Guest house 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
Guest house in Trinity Bellwoods
4.91 out of 5 average rating, 152 reviews

Cozy & Bright Private Suite in Trinity Bellwoods

SarahRating, 5 stars1 week ago
Easy to follow instructions for check in. Lovely little suite. On a really nice road. Friendly hosts. Would recommend and would stay again!
Superhost
Guest house 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
Guest favourite
Guest house 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
Guest house 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 house rentals with a patio

Superhost
Guest house 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
Guest favourite
Guest house in Lincoln
4.96 out of 5 average rating, 113 reviews

Loft in Jordan: private balcony, close to wineries

KimberlyRating, 5 stars1 day ago
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
Guest house in Meadowvale Village
4.74 out of 5 average rating, 116 reviews

Luxurious Apartment overlooking Ravin & Pool

MariyamRating, 5 stars4 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
Guest house in Saint Anns
5 out of 5 average rating, 11 reviews

Mid-century modern pool house

GwendalRating, 5 stars7 months ago
Shawn's airbnb was spectacular. He is such a friendly, responsive & accomodating host. The space itself is extremely unique. We appreciated the pool, the games outside, the fire pit, the scenery and general ambience. We truly enjoyed our stay. Shawns hosting & the space itself represents an overall exceptional experience. Thank you for hosting us. We will be back forsure!
Top guest favourite
Guest house in Brantford
4.95 out of 5 average rating, 60 reviews

Zen Rustic coach house quiet private

HillaryRating, 5 stars1 month ago
An incredible, relaxing stay. Thank you, Marlene
Top guest favourite
Guest house in Stoney Creek
4.97 out of 5 average rating, 35 reviews

Garden Home

BarbaraRating, 5 stars1 month ago
Beautiful Air Bnb. We have stayed there several times. It has always been very clean and easy to access. Kurtis is very pro active sending the access code and details about check in. He has also been very accommodating to requests we have made to change our dates. Highly recommend. We will be back.
Top guest favourite
Guest house in Copetown
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 favourite
Guest house 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!

Guest house rentals with a washing machine and dryer

Guest favourite
Guest house 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
Guest house 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!
Superhost
Guest house 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
Guest house in Richmond Hill
4.97 out of 5 average rating, 72 reviews

"Modern Urban Studio Retreat"

KristianRating, 5 stars1 week ago
Thanks for the wonderful stay. We had a very good time on site. The apartment is small but still very cozy and therefore definitely recommended. It was very clean. The communication was easy and straightforward.
Top guest favourite
Guest house 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
Guest house in Barrie
4.99 out of 5 average rating, 161 reviews

Warnica Coach House

RichardRating, 5 stars1 week ago
My wife and I had a great stay. They thought of everything. So comfortable and private. Walking distance to downtown Barrie and the waterfront. Great stay! We will be returning.
Superhost
Guest house in Richmond Hill
5 out of 5 average rating, 4 reviews

Charming Cozy Studio w/ Private Entrance & Parking

RudiRating, 5 stars2 months ago
Really enjoyed my stay, clean and friendly service. Woyld definitely book here again.
Guest favourite
Guest house in Richmond Hill
5 out of 5 average rating, 7 reviews

Cozy Studio with Private Entrance

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

Quick stats about guest house rentals in Caledon

  • Total rentals

    30 properties

  • Nightly prices starting at

    £23 before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

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