Holiday rentals in Caledon

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Top-rated holiday rentals in Caledon

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 209 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

12–19 Nov

£108 per night

Guest favourite

Tiny home in Acton

4.98 out of 5 average rating, 194 reviews

Farmview Sunset Cabin

Welcome to our tiny Farmview Cabin that is nestled in the middle of our private oasis located in Acton ON. Our 50 acre farm has spectacular views from every direction. Our horses, , swans, and miniature goats are here to greet you as well. This unique space will allow you to enjoy the beautiful outdoors during the day and a cozy warm space in the evenings! Continental Breakfast fixings are included. We are more than happy to accommodate vegan/plant based/gluten free meals as well.

31 Oct – 7 Nov

£119 per night

Guest favourite

Tiny home in Belwood

4.93 out of 5 average rating, 191 reviews

Uniquely Pure Bunkie Getaway in Belwood

Stay on a quiet property amongst trees at the Uniquely Pure Bunkie in Belwood. Enjoy your own space with a firepit, a cozy place to sleep, and a seasonally available outdoor shower (closes Oct 1st until spring). The owner lives on same property as Uniquely Pure Studio, where you can book massage therapies & yoga classes, or purchase products from our aromatherapy and culinary creations line during your stay (contact in advance for availability). Sorry, NO KIDS (for safety) & NO PETS!

2–9 Jan

£81 per night

Guest favourite

Guest suite in Orangeville

4.92 out of 5 average rating, 656 reviews

Private Hot Tub - Headwaters Retreat

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with en-suite bathroom, Apple TV, Netflix, and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

8–15 Dec

£71 per night

Guest favourite

Shipping container in Caledon

4.93 out of 5 average rating, 15 reviews

High Meadows Escape

Enjoy a cozy and quiet winter getaway before the holidays! A beautiful view of the blanket of snow covering the surrounding forest, a crackling fire inside or out and twinkling lights in this serene escape. Hidden among acres of forest, enjoy your private, tranquil, nature escape. Located upon a hill, with a private deck to enjoy meals overlooking the pond. Enjoy this escape no matter the season, indulging in cozy fire nights, skiing, snowshoeing, hiking, picnics and so much more.

17–24 Dec

£104 per night

Guest favourite

Cabin in Erin

4.94 out of 5 average rating, 275 reviews

Erin Cabin Getaway and Bunkie

Take it easy at this unique and tranquil getaway. Located steps from Calerin Golf Course (350 m) and includes many amenities, such as: a BBQ, patio w/ dining area, private hot tub, acres of groomed trails, games galore, pool table, fire pit, comfy queen bed w/ separate heated bunkie with a second queen bed and more! Optional pull out available, please inquire within (fee may apply). 2 km or 5 mins, from the picturesque town of Erin. Lots of restaurants, shops, and plenty to do!

20–27 Mar

£215 per night

Guest favourite

Guest suite in Mono

4.98 out of 5 average rating, 65 reviews

Welcome to a Sweet Suite

Forget your worries in this spacious and serene space. Enjoy the hiking trails at Mono Cliffs and Island Lake or an afternoon of wine tasting at Adoma Winery. Golf/ski is only 5km away at beautiful Hockley Valley. Enjoy a 5 star dinner at one of the fabulous restaurants in Orangeville. After a busy day return to your cozy queen size bed for a great night sleep. In the morning no need to head out for coffee as it is available for brewing on site. Cream and sugar provided.

13–20 Jun

£76 per night

Guest favourite

Cabin in Mono

4.94 out of 5 average rating, 272 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

2–9 Dec

£152 per night

Guest favourite

Guest suite in Mono

4.98 out of 5 average rating, 268 reviews

Mono - Charming, Rustic 150 Year Carriage House

This rustic space is perfect for a weekend getaway, year round. Close to ski hills, nature trails and the quaint town of Orangeville the Carriage house will provide you the authentic feel of our iconic cabin in the woods with the sophistication and comforts of your personal retreat for the weekend. The interior design is eclectic, funky and perfectly contrasts the rustic charm of the 140 year old, hand cut wooden beams and the overall log cabin environment.

28 Aug – 4 Sept

£94 per night

Guest favourite

Flat in Caledon

4.93 out of 5 average rating, 69 reviews

Separate apartment with pool, on golf course.

This is a comfortable, newly renovated studio apartment with separate entrance and private inground pool. It is decorated with Restoration Hardware furniture, features a fully-functioning kitchen, and access to a patio with outdoor barbeque. It is nestled in a tranquil setting on the back of the Caledon Woods golf course with easy access to highways leading to Toronto, Pearson International Airport (30 minutes), and the Caledon Equestrian Park (5 minutes).

17–24 Oct

£74 per night

Guest favourite

Guest suite in Caledon

4.98 out of 5 average rating, 89 reviews

Casa Caledon-Secluded Suite Surrounded by Nature

Take it easy at this unique and tranquil getaway on 3 acres of land The suite is close to conservation areas Cheltenham Badlands, Fork of the Credit and Terra Cotta Bruce trail, golf courses, restaurants, bakeries, butchers, farm produce and city needs are close Each season is wonderful Spring/summer has lush forests, the pond and fire pit Fall walks with the beautiful colours Winter has a white blanket and access to winter sports

4–11 Oct

£92 per night

Guest favourite

Guest house in Schomberg

4.93 out of 5 average rating, 342 reviews

Country Cabin for Long and Short Stays Queen bed

Our Country Cabin get-away is perfect for those looking to get out of the city and back to nature for a short or extended stay! Enjoy a little winter getaway and share our paradise in the countryside and be part of it all. You’ll love our location, full kitchen, access to camp fire pit, propane bbq, wifi internet, 40" Smart TV, three piece bathroom, laundry facilities and more.

17–24 May

£100 per night