
Guest house holiday rentals in Caledon
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Top-rated guest house rentals in Caledon
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Popular amenities for guest house rentals in Caledon
Family-friendly guest house rentals

Private Estate Coachhouse + Hot Tub near NOTL!
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 !

The Carriage House @ Mingle Hill
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!

Self Contained Luxury Studio Coach House
The place is great. Well situated and very clean. Very private and the hosts we very welcoming.

Country Cabin Escape | King Bed | Pet Friendly
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!

Cozy & Bright Private Suite in Trinity Bellwoods
Easy to follow instructions for check in. Lovely little suite. On a really nice road. Friendly hosts. Would recommend and would stay again!

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

Sunny Pines Farm Studio Tennis Court/Bruce Trail
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.

Modern Country Escape
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

Lovely & Cozy Apartment lots of natural light
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

Loft in Jordan: private balcony, close to wineries
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!

Luxurious Apartment overlooking Ravin & Pool
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!

Mid-century modern pool house
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!

Zen Rustic coach house quiet private
An incredible, relaxing stay. Thank you, Marlene

Garden Home
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.

Headwater Haven | 2 King-Beds
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.

Spacious fully private studio basement & parking
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

Incredible summer2025 sale Lux. fully private unit
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.

The Lexington Loft - A Modern & Industrial BNB
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!

bright charming 2bdrm private suite walk to Falls
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! ❤️

"Modern Urban Studio Retreat"
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.

Cozy guest unit
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.

Warnica Coach House
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.

Charming Cozy Studio w/ Private Entrance & Parking
Really enjoyed my stay, clean and friendly service. Woyld definitely book here again.

Cozy Studio with Private Entrance
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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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Blue Mountain Village
- Budweiser Stage
- Distillery District
- Port Credit
- Horseshoe Resort
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Exhibition Place
- CF Toronto Eaton Centre
- Toronto Zoo
- TPC Toronto at Osprey Valley
- Massey Hall
- Whistle Bear Golf Club
- Royal Woodbine Golf Club
- Harbourfront Centre
- Yonge-Dundas Square
- Snow Valley Ski Resort
- Trinity Bellwoods Park
- BMO Field
- Royal Ontario Museum