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Holiday houses in Caledon

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Quick stats about holiday rentals in Caledon

  • Total holiday rentals

    Explore 1,690 holiday rentals in Caledon

  • Nightly prices starting at

    Caledon holiday rentals start at $14 AUD per night before taxes and fees

  • Verified guest reviews

    Over 37,010 verified reviews to help you choose

  • Family-friendly holiday rentals

    640 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 240 rentals that welcome pets

  • Holiday rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    820 properties have a dedicated workspace

  • Wi-Fi availability

    1,580 of Caledon holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Caledon rentals

  • 4.7 Average rating

    Caledon stays receive an average rating of 4.7 out of 5 from guests

Top-rated holiday rentals in Caledon

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

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Top Guest favourite
Apartment in Orangeville
5.0 out of 5 average rating, 18 reviews

The Green Lodge - Upper Level Raised Bungalow

Kick back and relax in this calm, stylish and extremely well equipped home from home. Fully self contained and private upper level Bungalow complete with 1 large off road parking space. This open plan delight is beautifully furnished with kitchen, island, dining and living space as one. Then to the rear, 2 separate bedrooms and bath room. A rear door leads to a sun filled 225 sq ft deck overlooking the tree backed rear garden, perfect for those long summer nights with friends and family.

Top Guest favourite
An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.
Cottage in Mono
4.95 out of 5 average rating, 162 reviews

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

Superhost
An aerial view captures the waterfront trailer set against lush greenery, with a private deck featuring seating arrangements. Nearby, two kayaks await by the water, and a fire pit is surrounded by logs. The tranquil lake reflects the surrounding foliage.
Tiny home in Action
4.85 out of 5 average rating, 150 reviews

Lakefront 1 bedroom tiny home

Reconnect with nature at this unforgettable escape. Enjoy a wonderful stay in our lovely waterfront trailer located on Breezes Trailer park. It is a private quiet trailer park with 15 acres of nature and private access to Fairy Lake (Acton). Trailer is suitable for couple or small family. It is suited to people looking to relax and enjoy the scenery, explore the lake on kayak, exercise and explore on water bikes, fishing in the lake, enjoy some outdoor movies or campfire or under the stars.

Guest favourite
The modern tiny home features a black exterior and a large glass front, allowing natural light to illuminate the interior. A simple outdoor seating area with two chairs is visible, surrounded by lush greenery and trees, creating a connection with the serene natural surroundings.
Tiny home in Arthur
4.96 out of 5 average rating, 405 reviews

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Superhost
The exterior of a modern villa is presented, featuring large windows and a mix of brick and wooden elements. A spacious concrete area surrounds the house, and trees frame the background under a colorful twilight sky.
Farm stay in Caledon East
4.92 out of 5 average rating, 75 reviews

Beautiful Villa on Hill

Welcome to Beautiful Villa on Hill, a secluded paradise nestled on App. 3 acres of ravine property in Caledon East. Surrounded by a serene forest, a flowing stream, and private walking trails, Villa offers complete tranquility and privacy. With stunning panoramic views of nature, our spacious villa features 5 bedrooms and 4 full bathrooms, comfortably accommodating families or groups looking for the ultimate escape. Villa provides the perfect blend of relaxation and natural beauty.

Superhost
Home in Caledon
4.74 out of 5 average rating, 39 reviews

8 Acre Retreat | 5 min to TPC Osprey + Hot Tub!

Enjoy peaceful summer evenings on the patio ☀️ surrounded by nature on a private 8-acre property only 1 hr from Toronto. • 8 min from TPC Osprey 🏌️ • 2 spacious primary bedrooms w ensuites • Electric fireplace • Starlink Wi-Fi 🌟 • Smart TV • Private & nearby nature trails Start your mornings w coffee on the patio. Spend the day exploring trails or golfing nearby, then unwind at your calm, stylish retreat. Perfect for families, couples, & golfers looking to escape the city.

Guest favourite
An inviting outdoor space features a wooden pergola with string lights, surrounding a dining table and seating area. A private hot tub is positioned nearby, with lush greenery and vibrant flower arrangements enhancing the serene environment.
Cabin in Erin
4.9 out of 5 average rating, 537 reviews

Cabin stay and play! 10 mins to Canadian Open!

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!

Top Guest favourite
A spacious living area features a blue sofa with a light throw, positioned beside a circular coffee table. Wall art adorns the white walls, and natural light filters through a decorative window. A white cabinet and a small plant complete the cozy atmosphere.
Loft in Orangeville
4.98 out of 5 average rating, 182 reviews

Hockley Haven

Kick back and relax in this calm, stylish space. Cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.

Guest favourite
The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.
Dome in Uxbridge
4.86 out of 5 average rating, 138 reviews

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

Guest favourite
A charming exterior of the Clayhill Bunkie is presented, featuring a dark blue wooden facade with a steeply pitched roof. Two windows, adorned with flower boxes, flank a central door that is decorated with a natural wreath. Lush greenery surrounds the entrance, enhancing the serene setting.
Guesthouse in Halton Hills
4.92 out of 5 average rating, 185 reviews

The Clayhill Bunkie

Semi off-grid bunkie on The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, Glen Williams, Terra Cotta, & Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a fire. 1 basket of wood is included, adding great value. You WILL hear wildlife and farm animals here. Rural property, limited electricity, beautiful views. This is NOT a hotel room.

Top Guest favourite
Guest suite in Hamilton, Dundas
4.99 out of 5 average rating, 78 reviews

Summertime! Steam shower+breakfast+rooftop hottub

Nestled in a picturesque escarpment community overlooking the historic town of Dundas, The Hayloft is a charming getaway for anyone looking for an escape and a breath of fresh air. Relax in the steam shower inside or the hot tub on the fully private rooftop deck overlooking gardens. Take a nap on the lounge chairs. Visit with the chickens, make friends with the fish or the frogs. Unwind at night with a movie in bed, with breakfast (surcharge) in the morning.

Top Guest favourite
A private detached apartment is visible nestled among tall trees and lush greenery. The wooden exterior of the structure blends harmoniously with the natural surroundings. A pathway leads towards the entrance, framed by a vibrant landscape of ferns and colorful shrubs.
Guest suite in Caledon
4.99 out of 5 average rating, 156 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

Popular amenities for Caledon holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Caledon's top sights

Bramalea City Centre

124 locals recommend

Hockley Valley Resort - Golf, Spa and Ski

91 locals recommend

Rose Theatre Brampton

93 locals recommend

Cheltemham Badlands

86 locals recommend

Mount Chinguacousy

82 locals recommend

Gage Park

81 locals recommend

Other great holiday rentals in Caledon

Guest favourite
Home in Caledon
5.0 out of 5 average rating, 6 reviews

Stylish Caledon Retreat | 3BR • Office • Treadmil

Guest favourite
Home in Caledon
4.93 out of 5 average rating, 80 reviews

Modern Family Home•Fireplace•Backyard•NearBrampton

Superhost
A spacious living area is presented, featuring a sectional sofa positioned around a glass coffee table. Light wood flooring extends throughout the space, complemented by subtle wall decor. Natural light is provided by recessed lighting, illuminating the modern design and neutral color palette.
Guesthouse in Caledon
4.76 out of 5 average rating, 49 reviews

Guesthouse Hideaway Caledon 3Bath • 3Beds

Guest favourite
A well-lit bedroom features a spacious bed with crisp white linens and neatly arranged towels. Two nightstands with lamps are positioned on either side, while a stylish framed piece of art decorates the wall. A mirrored closet adds a touch of spaciousness to the room.
Guesthouse in Caledon
4.93 out of 5 average rating, 29 reviews

Cozy Private Basement Bedroom with ensuite

Guest favourite
Home in Palgrave
4.96 out of 5 average rating, 27 reviews

Relaxing Luxury Palgrave Cottage w/pool on 3 acres

Top Guest favourite
Cabin in Guelph/Eramosa
4.99 out of 5 average rating, 100 reviews

Fern Hill Cabin

Top Guest favourite
Home in Alton
5.0 out of 5 average rating, 22 reviews

Little blue haven

Top Guest favourite
A rustic log cabin is framed by lush greenery and colorful flowering plants. A stone pathway leads to the entrance, which is accessible via a set of stairs. A small pond with rocks is visible in the foreground, enhancing the garden's natural appeal.
Cabin in Shelburne
4.97 out of 5 average rating, 69 reviews

Cabin in Mono.

When is the best time to visit Caledon?

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Avg. price$99 AUD$102 AUD$98 AUD$102 AUD$108 AUD$120 AUD$112 AUD$116 AUD$108 AUD$105 AUD$101 AUD$101 AUD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

Frequently Asked Questions

  • What are the best places to stay in Caledon?

    Accommodations in Caledon often cluster around village centers, countryside estates, and areas near parks. Many stays are uniquely set on scenic farmland or at historic sites with local charm.

  • What are the best things to do in Caledon with kids?

    Families often explore parks, local farms, and nature centers around Caledon. The Alton Mill Arts Centre has creative activities, and kid-friendly trails offer safe spots for outdoor play and discovery.

  • What are some of the best things to do in Caledon?

    Explore the Cheltenham Badlands, view art exhibitions at the Alton Mill Arts Centre, and hike natural trails in Forks of the Credit Provincial Park. Local markets and village events add to the mix.

  • How is the weather in Caledon?

    Caledon has cold winters around 12–32°F (-11–0°C), and mild fall days near 49–70°F (10–21°C). Spring and summer often bring moderate temperatures and a blend of sunny and rainy days.

  • When is the best time to visit Caledon?

    Late spring and early autumn are frequently suggested, when mild temperatures prevail and outdoor landscapes are vibrant. Many travelers also visit during seasonal festivals and fruit harvest periods.

  • What are the best places to visit in Caledon?

    Frequently suggested spots in Caledon include the Cheltenham Badlands, the Alton Mill Arts Centre, and the Forks of the Credit Provincial Park. Many visitors also explore charming historic villages around town.

  • What are some hiking trails in Caledon?

    Caledon has hiking paths across Forks of the Credit Provincial Park, the Bruce Trail, and along the Cheltenham Badlands. Trails range from leisurely river walks to steeper woodland climbs.

  • What are some family activities we can do in Caledon?

    Families often explore outdoor parks, visit working farms for animal encounters, and join art workshops at the Alton Mill Arts Centre. Nature walks and riverside picnics are a staple for visitors with children.

  • What are some of the best day trip ideas from Caledon?

    Popular day trips from Caledon include exploring nearby provincial parks, visiting local arts and crafts centers, and discovering small towns with historic sites, markets, and gardens. Wine and cider tasting tours are a favorite for adults.

  • Are there any pet friendly accommodations available in Caledon?

    Caledon has pet-friendly accommodations, particularly near nature trails, rural retreats, and village hubs. Many hosts welcome pets, making it easy to explore outdoor spaces with your animal companions.

  • What are some local tips for visiting Caledon?

    Locals often suggest packing layers, as weather can shift quickly, and exploring outdoor spaces early in the day. Many visitors enjoy following scenic country roads, especially during autumn foliage and spring bloom.

  • What is Caledon known for?

    Caledon is known for its natural landscapes, rolling hills, and the distinctive Cheltenham Badlands. The area has a blend of rural traditions and vibrant arts communities.

  • What are the best hidden gems to explore in Caledon?

    Caledon has scenic spots like the quiet sections of the Bruce Trail, area waterfalls, and local pottery studios. Small heritage villages and farm stands are often recommended for unique finds.

  • What are the best foods to try in Caledon?

    Caledon has farm-to-table cuisine, locally made cheeses, and fresh seasonal produce. Bakeries around town frequently suggested Canadian butter tarts and pastries, and area farmers’ markets feature maple syrup and berry preserves.

  • What should I bring for a trip to Caledon?

    Pack sturdy walking shoes, weather-appropriate clothing, a reusable water bottle, and sun protection. A camera is recommended for scenic spots, and layers keep you comfortable as temperatures vary throughout the day.

  • What is the nightlife in Caledon like?

    Caledon’s nightlife centers on local pubs, casual eateries, and occasional live music in village venues. Events often reflect relaxed rural hospitality and community gatherings rather than crowded clubs.

  • What are the most popular events or festivals in Caledon?

    Caledon hosts art fairs, seasonal farmers’ markets, and festivals rooted in local heritage throughout the year. Summer outdoor concerts and autumn harvest celebrations are frequently suggested, especially around late spring and Labor Day weekend.

  • Are there family friendly vacation rentals in Caledon?

    Caledon has family-friendly vacation rentals in areas near parks, village centres, and natural attractions. Rentals with spacious layouts and outdoor spaces are often favored by families visiting the region.

Destinations to explore