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Guesthouse holiday rentals in Caledon

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Caledon guesthouses

Family-Friendly guesthouses

Top Guest favourite
Guesthouse in St. Catharines
4.99 out of 5 average rating, 422 reviews

Private Estate Coachhouse + Hot Tub near NOTL!

KarlRating, 5 stars3 weeks ago
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.
Guest favourite
Guesthouse in Oakville
4.93 out of 5 average rating, 198 reviews

Self Contained Luxury Studio Coach House

IeboubenRating, 5 stars6 days ago
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!
Top Guest favourite
Guesthouse in Saint Anns
4.98 out of 5 average rating, 197 reviews

The Carriage House @ Mingle Hill Farm

JodiRating, 5 stars2 weeks ago
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
Guest favourite
Guesthouse in Niagara-on-the-Lake
4.93 out of 5 average rating, 321 reviews

On the Vineyard @ 1068, Niagara on the Lake

KellyRating, 5 stars4 days ago
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.
Guest favourite
Guesthouse in Trinity-Bellwoods
4.92 out of 5 average rating, 155 reviews

Cozy & Bright Private Suite in Trinity Bellwoods

LizRating, 5 stars1 week ago
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!
Top Guest favourite
Guesthouse in Leslieville
4.93 out of 5 average rating, 314 reviews

Free Parking 2BD Queen St. East

MitchRating, 5 stars1 month ago
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!
Superhost
Guesthouse in Bronte West
4.6 out of 5 average rating, 10 reviews

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

JulieRating, 5 stars4 months ago
A truly intimate and comfortable internet spot perfect for a vacation
Guest favourite
Guesthouse in Lincoln
4.81 out of 5 average rating, 429 reviews

Cozy Rustic Cabin in Wine Country

KerryRating, 5 stars2 weeks ago
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

Top Guest favourite
Guesthouse in Mono
4.89 out of 5 average rating, 36 reviews

Mono Countryside Home & Farm

JoeRating, 5 stars3 weeks ago
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!
Guest favourite
Guesthouse in Hamilton
4.95 out of 5 average rating, 110 reviews

Hollis Haven

LuisRating, 5 stars1 week ago
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.
Guest favourite
Guesthouse in Lincoln
4.95 out of 5 average rating, 124 reviews

Loft in Jordan: private balcony, close to wineries

RachelRating, 5 stars2 weeks ago
Wonderful! Super cute and clean loved it thank you so much!! :)
Top Guest favourite
Guesthouse in Niagara Falls
5 out of 5 average rating, 186 reviews

Bosco Hilltop Hideaway

OmarRating, 5 stars4 days ago
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!
Top Guest favourite
Guesthouse in Fergus
5 out of 5 average rating, 21 reviews

Millcreek Riverfront Retreat Elora/Fergus

SarahRating, 5 stars4 days ago
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.
Guest favourite
Guesthouse in Lincoln
4.94 out of 5 average rating, 172 reviews

Little Blue Barn on the Bench

CarolynRating, 5 stars2 weeks ago
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.
Guest favourite
Guesthouse in St. Jacobs
4.98 out of 5 average rating, 52 reviews

St.Jacobs Oasis Retreat Hot Tub, Sauna,cold plunge

ShaileeRating, 5 stars5 days ago
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.
Guest favourite
Guesthouse in Aurora
4.91 out of 5 average rating, 150 reviews

Adorable Guesthouse Apartment With Free Parking

MargotRating, 5 stars1 month ago
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

Top Guest favourite
Guesthouse in Kitchener
5 out of 5 average rating, 46 reviews

Calm, Clean and Convenient

EdenRating, 5 stars1 week ago
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 :)
Superhost
Guesthouse in Pickering
5 out of 5 average rating, 4 reviews

Romantic Private Guest House

KunalRating, 5 stars5 months ago
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.
Guest favourite
Guesthouse in York
5 out of 5 average rating, 27 reviews

Junction Private Laneway Suite with Backyard

MārtiņšRating, 5 stars1 day ago
Nice place, quiet neighbourhood
Top Guest favourite
Guesthouse in Richmond Hill
4.96 out of 5 average rating, 84 reviews

"Modern Urban Studio Retreat"

TeresaRating, 5 stars1 week ago
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.
Guest favourite
Guesthouse in Markham
4.93 out of 5 average rating, 29 reviews

Chic & Cozy 1Bed Guest Suite

Shehzer KhanRating, 5 stars1 month ago
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.
Top Guest favourite
Guesthouse in Barrie
4.98 out of 5 average rating, 82 reviews

Rustic luxury chalet near beach with private pool

DanaRating, 5 stars3 weeks ago
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!
Superhost
Guesthouse in Newmarket
4.71 out of 5 average rating, 21 reviews

Tranquil Spacious Unit

JulieRating, 5 stars1 week ago
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.
Guest favourite
Guesthouse in Feversham
4.92 out of 5 average rating, 181 reviews

Guesthouse Getaway

RitaRating, 5 stars3 months ago
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