
Guesthouse holiday rentals in Caledon
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Top-rated Guesthouses in Caledon
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Caledon guesthouses
Family-Friendly guesthouses

Private Estate Coachhouse + Hot Tub near NOTL!
Carl & Sherrie are wonderful hosts, and their coach house is the most amazing Airbnb that we have had the pleasure to call home away from home! We stayed for three nights, but could have easily enjoyed this place for a month. It’s cozy, beautiful, peaceful & was such a great launching point for all we did in Niagara Falls, Niagara on the Lake, and horseback riding out in the country. They really put quality workmanship into the bright kitchen, the glistening bathroom and cool shower, and the private courtyard and hot tub is all that they described! No surprise that this is rated a Guest Favorite.

Self Contained Luxury Studio Coach House
I really enjoyed my stay! The place was clean, cozy, and exactly as described. The location was perfect, and the host was friendly and responsive. I would definitely stay here again and highly recommend it to anyone visiting the area. Thank you for the great experience!

The Carriage House @ Mingle Hill Farm
Lovely place for a quick getaway with my husband and 1 year old. Beautiful area and so many birds to listen to. Lots of things to do nearby

On the Vineyard @ 1068, Niagara on the Lake
There are lots of great things about Lisa’s farmhouse, but for me it was the spaciousness, huge windows through the whole house, tons of light and the quaint and pretty decor. The bedrooms are lovely and the bathrooms were well-equipped and spotless. Beds are comfy. Kitchen newly renovated. We enjoyed sitting out in the backyard on a lovely summer’s day having our morning coffee. It was the perfect place for us and we enjoyed our stay very much.

Cozy & Bright Private Suite in Trinity Bellwoods
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!

Free Parking 2BD Queen St. East
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!

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

Cozy Rustic Cabin in Wine Country
My dog and I had the most amazing staycation at Joe's cabin and I don't know who enjoyed it more - me or him! The location is beautiful - so peaceful and so green and lush. The cabin has everything you need and is centrally located to many wineries and easy to get to Niagara-on-the-Lake or surrounding areas. Joe and Emma are super friendly and helpful and we hope to return again next year!
Guesthouses with a patio

Mono Countryside Home & Farm
absolute perfect spot for doing a chunk of the Bruce Trail would be a good base camp for all of the Dufferin Hi—Lands and deep into the Blue Mountain Section. So many good restaurants around.For after your hike, this place feels off the beaten path, and is literally just 1 km from the trail!

Hollis Haven
Great to be back. Second year in a row that we stay with Ron and we felt welcome. Great space, great kitchen with utensils and everything that you need to make a meal, spacious room and living area in addition to having a nice bathroom with plenty of towels and the necessary toiletries. The hot tub is always enjoyable, plus having plenty of seats outside in case you want to get some fresh air. We throughly enjoyed our stay and will definitely be back soon.

Loft in Jordan: private balcony, close to wineries
Wonderful! Super cute and clean loved it thank you so much!! :)

Bosco Hilltop Hideaway
Kelli’s place was magical — so much so that I actually proposed to my girlfriend on the back deck during our stay. Private, serene, and just a short distance from both the Falls and Niagara-on-the-Lake. Hope we’ll be back someday!

Millcreek Riverfront Retreat Elora/Fergus
We had a fantastic stay at the Millcreek Retreat! The location was beautiful, it felt completely private and had gorgeous views over the river from the balcony and bedroom. The place was spotless and had everything that we could have needed during our stay. Would recommend this Airbnb to anyone and everyone! It was the perfect location for our little babymoon getaway.

Little Blue Barn on the Bench
Really enjoyed our stay! It was quiet and clean with a very responsive host. Definitely recommend RPM bakery in Jordan. The place is close to a ton of great wineries and outdoor activities like the Bruce Trail. Would definitely consider going back if we find ourselves in the area.

St.Jacobs Oasis Retreat Hot Tub, Sauna,cold plunge
We had a very enjoyable and relaxing time here! Perfect for a peaceful weekend getaway. The hot tub and sauna were well maintained and enjoyable, and the indoor space was clean and comfortable as well. Christine was a very helpful and responsive host. The location was also perfect to access local restaurants and the farmer's market.

Adorable Guesthouse Apartment With Free Parking
Clean and comfortable spot for one person, has everything you need! Helpful to note the bed is just a mattress in the loft (not a proper bed).
Guest house rentals with a washing machine and dryer

Calm, Clean and Convenient
Beautiful community, wonderful host and tidy house. Rosanne offers a comfortable and flawless place for visitors to stay. There is anything you can imagine to spend time with your family, including kitchen supplies, bath products, and more. Thanks to Rosanne and her space, I had a smooth and memorable convocation experience with my parents here in Waterloo. Definitely one of the best moments of my life! Thank you, Rosanne, for making this happen :)

Romantic Private Guest House
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.

Junction Private Laneway Suite with Backyard
Nice place, quiet neighbourhood

"Modern Urban Studio Retreat"
Wonderful place to stay for my business event. The space had everything I needed and the little extras and personalization was a great touch. Everything was so clean and that is important to me. I'd stay at this place anytime. Great host and great spot.

Chic & Cozy 1Bed Guest Suite
Had such a beautiful stay at this property! Shayan was incredibly nice and easy to communicate with, which made the whole experience even smoother. The property itself was very clean, well-maintained, and truly equipped with everything I needed. It’s a really lovely space—comfortable, thoughtfully set up, and in great condition. I would absolutely stay here again and highly recommend it to anyone looking for a relaxing and hassle-free stay.

Rustic luxury chalet near beach with private pool
We had a great time on our stay here. Just as described, the chalet provides privacy and comfort. The linens on the bed were to die for! Great space for relaxing with a small group and the island is perfect for a games night! They had coffee to get through the mornings and shower essentials as well. We would highly recommend this space for your next trip!

Tranquil Spacious Unit
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.

Guesthouse Getaway
Beautiful location, with clear directions on how to find. Hosts were flexible and allowed me to check-in early, which I appreciated so much. It snowed while I was there, and they had the driveway and parking area all cleared. The place was clean & cozy - I would stay again!
Quick stats about guesthouse rentals in Caledon
Total rentals
30 properties
Nightly prices starting at
$50 NZD 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
Wi-Fi availability
30 properties include access to Wi-Fi
Destinations to explore
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Blue Mountain Village
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- Massey Hall
- BMO Field
- Whistle Bear Golf Club
- Trinity Bellwoods Park
- Casa Loma
- Royal Woodbine Golf Club
- Dufferin Grove Park
- Royal Ontario Museum
- Royal Botanical Gardens