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Vacation rentals in Caledon

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Quick stats about vacation rentals in Caledon

  • Total vacation rentals

    Explore 1,580 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 41,440 verified reviews to help you choose

  • Family-friendly vacation rentals

    650 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 240 rentals that welcome pets

  • Vacation rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    760 properties have a dedicated workspace

  • Wifi availability

    1,500 of Caledon vacation rentals include wifi 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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Guest favourite
Apartment in Orangeville

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.

ValueLocationBathroom

4.91 out of 5 average rating, 33 reviews
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

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.

LocationFamilyWifi

4.95 out of 5 average rating, 171 reviews
Guest favourite
Home in Caledon

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!

ValueFamilyBreakfast

4.85 out of 5 average rating, 288 reviews
Guest favourite
A spacious living room is presented, featuring comfortable sofas and a coffee table centered on a soft area rug. A sleek entertainment unit with a television is visible, complemented by natural light filtering through large windows and subtle overhead lighting.
Home in Orangeville

Stunning 5 Bedroom Family Home

Beautiful and cozy home for families. This home has a fully equipped kitchen, a living & family room! You will feel completely relaxed with your family or friends. Steps from the downtown strip & top restaurants in the Dufferin Region. Just 10 minutes to Hockley Valley Ski Resort More affordable and comfortable for your kid's hockey tournaments or visiting family over the holidays! Stocked with towels, linens, a full kitchen, state of the art stainless steel appliances, & more!

LocationFamilyComfort

4.82 out of 5 average rating, 111 reviews
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

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.

FamilyLocationNearby

4.92 out of 5 average rating, 78 reviews
Superhost
Home in Caledon

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.

ValueFamilyOutdoor spaces

4.73 out of 5 average rating, 52 reviews
Top guest favourite
Home in Caledon

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.

LocationFamilyIndoor spaces

4.94 out of 5 average rating, 94 reviews
Superhost
Townhouse in Orangeville

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!

ValueFamilyCleanliness

4.84 out of 5 average rating, 187 reviews
Top guest favourite
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

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.

FamilyLocationBreakfast

5.0 out of 5 average rating, 56 reviews
Guest favourite
Home in Caledon East

Modern- Cozy House by Nature for Full Family of 13

Enjoy Comfort in our Private 5BR & 4.5WR Caledon Home - Perfect for family & friends gatherings surrounded by nature! ✓ Entire home to yourself – 100% privacy ✓ 5 spacious bedrooms – sleeps up to 13 guests! ✓ 4.5 modern washrooms ✓ Fully equipped kitchen with all cooking essentials ✓ Large Smart TV & High-Speed Wi-Fi for streaming ✓ Books & Cards for cozy family time Book your stay today & create unforgettable memories in comfort and style!

LocationFamilyKitchen

4.91 out of 5 average rating, 23 reviews
Top guest favourite
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

Elba Haus | 63-Acre Private Retreat + Hot Tub

Elba Haus is your 63-acre private retreat in Mono, Ontario — designed for unforgettable group stays. Soak in the hot tub, gather around the fire, and explore private forest trails. Minutes to wineries, breweries, cideries, dining, and golf at TPC Toronto at Osprey Valley. Perfect for wedding weekends, retreats, and family getaways near Cambium Farms, Adamo Estate, Caledon Valley Estate, Erin Estate and more.

FamilyLocationComfort

5.0 out of 5 average rating, 21 reviews
Top guest favourite
A serene scene at dusk captures three animals, including a cow and two horses, walking along a path in a pasture. Sunlight filters through trees in the background, creating a warm glow over the landscape.
Farm stay in Orangeville

3 separate sleeping rooms on 23-acre horse farm

Self-contained lower unit on a 23-acre horse farm. Sleeps 6; fully equipped kitchen, laundry facilities, separate entrance, internet, TV streaming. One full bathroom, outdoor sitting area, parking for 2 vehicles. Owner on premises. 15 minutes east of Orangeville. 10 minutes to Palgrave. 15 minutes to Hockley Valley Resort and 30 minutes to Mansfield. Minimum 2 nights. Discount for the week.

FamilyValueKitchen

4.98 out of 5 average rating, 63 reviews

Popular amenities for Caledon vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Caledon's top sights

Bramalea City Centre

129 locals recommend

Hockley Valley Resort - Golf, Spa and Ski

92 locals recommend

Rose Theatre Brampton

94 locals recommend

Cheltemham Badlands

90 locals recommend

Mount Chinguacousy

89 locals recommend

Gage Park

82 locals recommend

Other great vacation rentals in Caledon

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

Caledon Getaway

LocationFamilyIndoor spaces

4.93 out of 5 average rating, 43 reviews
Top guest favourite
A spacious dining area features a wooden table surrounded by upholstered chairs. Natural light fills the room through large windows, highlighting the modern décor and vaulted ceiling. A comfortable seating area with a couch and armchair sits adjacent, creating an inviting open-plan layout.
Apartment in Orangeville

A bright & chic 2 bedroom urban apartment

ValueLocationAccuracy

4.92 out of 5 average rating, 87 reviews
Guest favourite
Guest suite in Alton

Riverside Retreat | Golf & Wedding Stays

LocationValueComfort

4.84 out of 5 average rating, 38 reviews
Superhost
A spacious cottage exterior is highlighted by a large driveway and well-maintained landscaping. The entrance features a decorative archway, with steps leading up to the front door. Surrounding trees provide natural shade, enhancing the peaceful setting.
Cottage in Belfountain

Belfountain Retreat | Fire Pit, Trails & Nature

LocationValueView

4.71 out of 5 average rating, 98 reviews
Top guest favourite
Home in Palgrave

Luxury Private Cottage |Cozy Fall Retreat

LocationFamilyDecor

4.98 out of 5 average rating, 43 reviews
Top guest favourite
Home in Alton

Little blue haven

LocationFamilyNearby

4.95 out of 5 average rating, 39 reviews
Superhost
Home in Erin

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

ValueFamilyPool

4.71 out of 5 average rating, 38 reviews
Guest favourite
Home in Caledon

100% privacy 7 bed 6 bath with 7 beds Brand new

FamilyLocationCondition

4.96 out of 5 average rating, 28 reviews

When is the best time to visit Caledon?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$100 CAD$103 CAD$98 CAD$103 CAD$108 CAD$121 CAD$113 CAD$117 CAD$108 CAD$105 CAD$101 CAD$101 CAD
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