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Vacation rentals in Caledon

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Quick stats about vacation rentals in Caledon

  • Total vacation rentals

    Explore 1,690 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at R 164 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 37,010 verified reviews to help you choose

  • Family-friendly vacation rentals

    640 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 240 rentals that welcome pets

  • Vacation 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 vacation 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

  • Nearby attractions

    Caledon's top spots, include SilverCity Brampton Cinemas, Landmark Cinemas 7 Bolton, and Uptown Theatre

Top-rated vacation rentals in Caledon

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

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Guest favorite
Home in Caledon
4.92 out of 5 average rating, 79 reviews

Luxury Family Home•Fireplace•Backyard•NearBrampton

Your Stylish Home Away From Home ✨ Enjoy the comfort of a spacious 3-bedroom home minutes from Brampton. Perfect for families, wedding guests, business travelers, and hockey tournaments. Relax by the fireplace, cook in the fully equipped kitchen, and unwind in the private backyard. Whether you're here for work or a getaway, you'll enjoy fast Wi-Fi, comfortable living spaces and everything you need for a seamless stay. Prime location: 2 mins to shops, 20 mins to Mississauga, 30 mins to Toronto.

Guest favorite
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, 183 reviews

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or glamping? On The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, the villages of 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.

Top guest favorite
A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.
Cabin in Mono
4.95 out of 5 average rating, 346 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, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Top guest favorite
A modern kitchen is equipped with stainless steel appliances including a refrigerator and stove. A wooden dining table with four chairs sits in the center, complemented by a decorative vase filled with sunflowers. Ample storage is provided by the white cabinetry and countertop space.
Apartment in Orangeville
4.92 out of 5 average rating, 65 reviews

The Bee Hive - Lower Level Raised Bungalow

Kick back and relax in this calm, stylish and super equipped space. Fully self contained and private lower apartment to our home with the hosts living above. Open plan kitchen dining living area with 1 bedroom (queen bed) and 1 shower room with 8 ft ceilings. Newly renovated, almost everything new this year ready for the 2025 season. Home from home, calm and pleasant space with all the mod cons. 50" LG Smart TV, Full sized fridge freezer, dishwasher, stove, microwave and much more - Enjoy!

Top guest favorite
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, 156 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.

Top guest favorite
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
4.97 out of 5 average rating, 400 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
Home in Caledon
4.75 out of 5 average rating, 36 reviews

8 Acre Retreat | 5 min to Canadian Open 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 favorite
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, 528 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!

Guest favorite
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, 129 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.

Top guest favorite
Guest suite in Hamilton
4.99 out of 5 average rating, 73 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.

Guest favorite
Home in Erin
5 out of 5 average rating, 23 reviews

Bright & Spacious 3BR Home with Foosball Table

Welcome to this bright and spacious 3-bedroom, 2.5-bath getaway. Perfect for families, friend groups, or work trips. With open-concept living, a full kitchen, and a foosball table, this home offers the perfect blend of comfort and convenience. ✔ Sleeps up to 6 guests ✔ 3 comfortable bedrooms + 2.5 baths ✔ Open-concept kitchen, dining & living areas ✔ Foosball table & multiple hangout area ✔ 2 Free driveway parking spaces & modern finishes throughout

Top guest favorite
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, 154 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 vacation 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

Forks of the Credit Provincial Park

45 locals recommend

Gage Park

81 locals recommend

Mount Chinguacousy

82 locals recommend

Alton Mill Arts Centre

44 locals recommend

Other great vacation rentals in Caledon

Guest favorite
A serene winter scene shows a cozy bunkie nestled among snowy trees. The structure features large glass doors that invite natural light, while a private deck is visible, surrounded by fresh snow and evergreen trees, enhancing the peaceful atmosphere of the forested setting.
Shipping container in Caledon
4.95 out of 5 average rating, 59 reviews

High Meadows Escape

Guest favorite
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, 28 reviews

Cozy Private Basement Bedroom with ensuite

Guest favorite
Home in Caledon
5 out of 5 average rating, 7 reviews

Luxury Home for Families & Groups | Sleeps 8

Top guest favorite
A spacious basement kitchen is equipped with modern appliances, including a stainless-steel fridge and stove. The central island features two bar stools for casual dining. A comfortable living area is visible, highlighted by a large TV and a stylish electric fireplace. Natural light enters through small windows.
Guest suite in Caledon
4.95 out of 5 average rating, 62 reviews

Luxe Cinema Suite | Guest Favourite | 25m to YYZ

Top guest favorite
Cabin in Guelph-Eramosa
4.99 out of 5 average rating, 94 reviews

Fern Hill Cabin

Top guest favorite
Home in Alton
5 out of 5 average rating, 20 reviews

Little blue haven

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, 46 reviews

Guesthouse Hideaway Caledon 3Bath • 3Beds

Guest favorite
Home in Caledon
4.89 out of 5 average rating, 27 reviews

Luxury 4BR Stay with Swim Spa, Golf & Fireplaces

When is the best time to visit Caledon?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 1,145 ZARR 1,178 ZARR 1,129 ZARR 1,162 ZARR 1,194 ZARR 1,309 ZARR 1,293 ZARR 1,342 ZARR 1,244 ZARR 1,211 ZARR 1,162 ZARR 1,162 ZAR
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

  1. Airbnb
  2. Canada
  3. Ontario
  4. Peel
  5. Caledon