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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 €9 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

Top-rated vacation rentals in Caledon

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

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Top guest favorite
A tranquil pond is surrounded by lush greenery and features fountains that gently spray water into the air. The area is well-maintained, providing a serene landscape for relaxation and contemplation.
Apartment in Erin
5.0 out of 5 average rating, 88 reviews

Country Getaway in Erin

Forget all your worries in this private country retreat. Stay in our 2 storey private apartment located on a 38 acre lot, where peace and tranquility are at your doorstep. Enjoy long walks along tree-lined roads with picturesque views and perfect star gazing at night. Comfortable accommodations up to 4 with 1.5 bathrooms, and your own fully functional kitchen. Only 3 minutes from town where you can enjoy some good country hospitality. Coffee shop, bakery, ice cream shop and much more await you.

Top guest favorite
Home in Alton
5.0 out of 5 average rating, 27 reviews

Little blue haven

Nestled in the peacful village of Alton, this home is the perfect base to explore all the area has to offer. Planning a wedding? you'll find several beautiful nearby wedding venues just minutes away. For relaxation and pampering, local spas provide indulgent treatments, while golf enthusiasts can enjoy nearby championship courses. Outdoor lovers will delight in hiking trails, mountian biking and winter skiing. Foodies can explore breweries, wineries, restaurants. Art lovers can visit galleries

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, 163 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
Home in Caledon
4.86 out of 5 average rating, 14 reviews

100% Private and Spotless ~Foosball ~Cozy Caledon

Welcome to your Private 3 Bedroom, 2.5 Washroom Caledon Retreat-Perfect for Families & Peaceful Getaways! ✔ Entire home to yourself ✔ 3 Bedrooms for cozy nights ✔ Modern open-concept living area ✔ Fully equipped kitchen stocked with essentials ✔ Smart TV+ High-Speed WiFi ✔ Foosball table for fun moments Nearby places for fun activities ✔ Albion Hills Conservation Park ✔ Palgrave Forest & Wildlife Area ✔ Local Community Skating Rinks Book with confidence and create unforgettable memories!

Guest favorite
Home in Caledon
4.86 out of 5 average rating, 272 reviews

Studio Apartment

Discover the perfect blend of comfort and convenience in this cozy studio apartment, ideally situated in the vibrant heart of Caledon. Key Features: Prime Location: Steps away from shops, cafes, and parks. Modern Amenities: Spacious living area, and stylish bathroom. Natural Light: Large windows that fill the space with warmth and brightness. Community Vibe: Enjoy the friendly neighborhood atmosphere and local events. This peaceful retreat, offers everything you need. Don't miss out!

Superhost
Home in Erin
4.74 out of 5 average rating, 31 reviews

Indoor Pool • Hot Tub • Heated Dome • 40 min GTA

Welcome to a peaceful 15-acre retreat in Erin, featuring 3+1 bedrooms and 5 bathrooms, plus a year-round heated indoor pool 🏊‍♀️. Enjoy scenic woodland trails, a heated indoor sports dome for mini soccer & volleyball ⚽🏐, and an outdoor wood-burning hot tub with beautiful views over a spring-fed pond 🐟. Complimentary breakfast items included, and support is always available by call or message. Perfect for families and groups —ideal for relaxing getaways, reunions, and nature escapes.

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
4.72 out of 5 average rating, 43 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 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, 544 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!

Superhost
Home in Caledon
4.93 out of 5 average rating, 85 reviews

Modern Family Home•Fireplace•Backyard•NearBrampton

Enjoy a comfortable 3-bedroom family home designed for relaxing stays, featuring a private backyard, cozy fireplace, fully equipped kitchen, fast Wi-Fi, and convenient parking. Perfect for families, wedding guests, hockey tournaments, business travellers, visiting relatives, relocations, and extended stays. Prime location just 2 minutes from local shops, 20 minutes to Mississauga, and approximately 30 minutes to Toronto—making it an ideal home base for your stay.

Superhost
Townhouse in Orangeville
4.85 out of 5 average rating, 175 reviews

Stylish 3 Bedroom Getaway in Orangeville

Nestled among tree sculptures and lakes, just steps away from downtown and minutes from the serene beauty of Island Lake Conservation Area. Our urban oasis is complete with a comfortable bed, fully equipped kitchen, chic living area, and private balconies. Be transported through time as you wander the streets of downtown, admiring vintage architecture and vibrant culture. Experience the magic of nature and city living combined in one unforgettable stay!

Top guest favorite
An open-concept living area features a spacious sectional sofa adorned with a variety of patterned cushions. A large wooden coffee table sits centrally, complemented by decorative candles. Bright windows provide natural light, offering views of the outdoors. The adjacent area includes a modern kitchen and dining space.
Guest suite in Caledon
5.0 out of 5 average rating, 53 reviews

Beautiful Retreat in Caledon

Welcome to your luxurious suite in the heart of beautiful Caledon. The perfect place to stay for travellers attending special events, seeking year-round outdoor adventure, or simply relaxing in a lovely setting. Many hiking / biking trails, equestrian, golf and skiing opportunities at your door step, or just relax and explore local shops, farmer's markets and restaurants. Located only 35 minutes NW of Pearson International Airport in Toronto.

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

Rose Theatre Brampton

93 locals recommend

Cheltemham Badlands

86 locals recommend

Mount Chinguacousy

82 locals recommend

Gage Park

81 locals recommend

Other great vacation rentals in Caledon

Guest favorite
Home in Caledon
4.83 out of 5 average rating, 36 reviews

Place to Relax with whole Family

Top guest favorite
An aerial view of Elba Haus showcases the spacious white facade surrounded by lush green fields. A pathway leads to a welcoming porch, while a picturesque lawn features a fire pit and lounge area. The backdrop displays gently rolling hills under a colorful sky at dusk.
Home in Orangeville
5.0 out of 5 average rating, 15 reviews

Elba Haus | 63-Acre Private Retreat + Hot Tub

Superhost
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
4.91 out of 5 average rating, 77 reviews

The Bee Hive - Lower Level Raised Bungalow

Top guest favorite
Townhouse in Brampton
5.0 out of 5 average rating, 29 reviews

Spacious 3Bed, 3Bath 2Parking, Pvt Yard, Fast Wifi

Superhost
A cozy living area is featured with a gray sectional sofa, adorned with decorative pillows. A round glass table rests on a patterned rug, complemented by wall art and a wall clock. Natural light filters through the window, enhancing the bright ambiance.
Apartment in Caledon
4.93 out of 5 average rating, 41 reviews

Caledon Getaway

Guest favorite
Home in Cheltenham
4.95 out of 5 average rating, 22 reviews

Indoor Pool & Hot Tub Villa | Sleeps 14

Superhost
Home in Shelburne
4.64 out of 5 average rating, 22 reviews

Farmhouse w/ Hot Tub | Private Country Retreat

Top guest favorite
An open-concept living area features a modern kitchen with stainless steel appliances and a dining table for four. A cozy seating arrangement is positioned around a simple coffee table, while a mounted television and wooden accent wall enhance the contemporary design.
Home in Orangeville
4.94 out of 5 average rating, 53 reviews

Orangeville 3BDRM House

When is the best time to visit Caledon?

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Avg. price€60€62€59€62€65€73€68€70€65€63€61€61
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