Holiday rentals in Caledon

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Top-rated holiday rentals in Caledon

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Guest favourite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 208 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...

28 Jul – 4 Aug

€ 126 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.

11–18 Dec

€ 139 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

€ 83 per night

Guest favourite

Shipping container in Caledon

4.93 out of 5 average rating, 14 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.

9–16 May

€ 122 per night

Guest favourite

Cabin in Erin

4.94 out of 5 average rating, 274 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!

30 Dec – 6 Jan

€ 259 per night

Guest favourite

Guest suite in Mono

4.98 out of 5 average rating, 64 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.

11–18 Jul

€ 89 per night

Guest favourite

Guest house in Mono

4.92 out of 5 average rating, 89 reviews

Mono Studio

Located in the beautiful Island Lake Estates community. The Mono studio is a private cozy little getaway from the hustle and bustle. The studio is surrounded by amenities that offer something for everyone. Enjoy wine tasting at Adamo Estates, take a walk on the Vicky Barron Trail, visit Mono Cliffs Park, ski or golf at Hockley Valley Resort or venture into Orangeville for some great local restaurants or a show at the Orangeville Theater. Twin bed expands to King size

26 Jun – 3 Jul

€ 107 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

30 Jul – 6 Aug

€ 178 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.

30 Sep – 7 Oct

€ 106 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).

1–8 Nov

€ 87 per night

Guest favourite

Guest suite in Schomberg

4.91 out of 5 average rating, 408 reviews

Romantic Country Suite for Couples with King Bed

Our Country Suite is all about Rustic Elegance. Come to our farm for a night, a weekend, or longer. Perfect place for a quiet, peaceful & relaxing weekend escape or a romantic getaway. You’ll love our rural location, full kitchen, wifi internet, 55" 4K Smart TV, three piece bathroom, laundry, propane BBQ, Patio access to propane fire pit. Enjoy walking trails in our bush, biking, close to nature and much more. Located about 50 min. from Toronto.

4–11 May

€ 117 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

28 Aug – 4 Sep

€ 108 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Caledon holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Caledon's top sights

Bramalea City Centre64 locals recommend

Trinity Common Mall26 locals recommend

Chinguacousy Park41 locals recommend

Albion Hills Conservation Park15 locals recommend

Cassie Campbell Community Centre7 locals recommend

William Osler Health System - Brampton Civic Hospital4 locals recommend

Other great holiday rentals in Caledon

Guest favourite

Bungalow in Terra Cotta

4.99 out of 5 average rating, 86 reviews

Country Cottage House, Cozy and Private

17–24 Aug

€ 144 per night

Guest favourite

Loft in Mono

4.98 out of 5 average rating, 59 reviews

Hockley Haven

23–30 May

€ 109 per night

Guest favourite

Farm stay in Loretto

4.92 out of 5 average rating, 26 reviews

Character-filled farm guest house on 8 acres

11–18 Aug

€ 128 per night

Guest favourite

Flat in Caledon

5.0 out of 5 average rating, 11 reviews

Caledon Getaway

24–31 Jan

€ 127 per night

Guest favourite

Guest suite in Orangeville

5.0 out of 5 average rating, 75 reviews

Garden Studio Apartment

28 Feb – 7 Mar

€ 98 per night

Guest favourite

Guest suite in Caledon

5.0 out of 5 average rating, 13 reviews

Beautiful Retreat in Caledon

20–27 Nov

€ 213 per night

Guest favourite

Guest house in Halton Hills

4.87 out of 5 average rating, 31 reviews

The Clayhill Bunkie

12–19 Aug

€ 84 per night

Guest favourite

Flat in Caledon

4.97 out of 5 average rating, 29 reviews

Private Bachelor Apartment

7–14 Jun

€ 91 per night

Show all

Quick stats about holiday rentals in Caledon

Total rentals	1.7K properties
Rentals with dedicated workspaces	910 properties have a dedicated workspace
Rentals with a pool	80 properties have a pool
Pet-friendly rentals	260 properties allow pets
Family-friendly rentals	570 properties are a good fit for families
Total number of reviews	28K reviews

Holiday rentals in Caledon

Top-rated holiday rentals in Caledon

Dome in Bradford West Gwillimbury

Tiny home in Acton

Guest suite in Orangeville

Shipping container in Caledon

Cabin in Erin

Guest suite in Mono

Guest house in Mono

Cabin in Mono

Guest suite in Mono

Flat in Caledon

Guest suite in Schomberg

Guest suite in Caledon

Holiday rentals for every style

Houses

Flats

Hotels

Popular amenities for Caledon holiday rentals

Stay near Caledon's top sights

Other great holiday rentals in Caledon

Bungalow in Terra Cotta

Loft in Mono

Farm stay in Loretto

Flat in Caledon

Guest suite in Orangeville

Guest suite in Caledon

Guest house in Halton Hills

Flat in Caledon

Quick stats about holiday rentals in Caledon

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore