House vacation rentals in Caledon

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Top-rated house rentals in Caledon

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Top guest favorite
The exterior of a log house is presented, showcasing a large balcony with flower boxes and a well-maintained garden featuring a pond. Lush greenery surrounds the property, complemented by a paved driveway and a striking wooden design that enhances its rustic charm.
Home in West Montrose
4.99 out of 5 average rating, 169 reviews

Austrian Log house

Nestled within walking distance of the Grand River between Elora & West Montrose sits a stunning "Austrian" built log house. Come and relax with a coffee by the fireplace on the frosty winter days or the outside firepit during warm summer nights. Ideal setting for family get togethers and nature enthusiasts. Plenty of space for everyone in this 2,800 sq. ft. home, with lots of quiet sitting areas, both inside & outside. Sorry we have a "no pet policy". HST is being charged BN70981 5336T

Top guest favorite
A cozy living area features a plush gray sofa and two bright armchairs, inviting relaxation. Natural light filters through the large windows, illuminating the wooden log walls and earthy decor elements, while a small coffee table sits in the center.
Home in Elora
4.99 out of 5 average rating, 234 reviews

Log Cabin in the heart of downtown Elora

The Cabin Elora is a beautiful rustic log cabin stylishly updated with modern and hand made furniture from a local artisan. You will enjoy a clean, bright and open concept space. Located in the heart of Elora, walking out the door into downtown yet nestled off the street giving you wonderful privacy and a quiet peaceful atmosphere. Features: • King size bed with Egyptian cotton sheets • Private patio overlooking Metcalfe St. and gardens • Clean, stocked kitchen • Perfect downtown location

Top guest favorite
A dining table is elegantly set with two decorative plates, glasses of varying sizes, and utensils arranged symmetrically. A soft glow is provided by a small candle flickering in a metallic holder, creating a subtle ambiance for mealtime.
Home in Vaughan
4.99 out of 5 average rating, 405 reviews

Quiet Vaughan Retreat near Wonderland & Hwy 400

Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, Cortellucci Hospital and transit.

Guest favorite
Home in Caledon
4.87 out of 5 average rating, 213 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!

Guest favorite
An open concept game room features a polished pool table at the center, with a bar area equipped with stools to one side. Large windows allow natural light to fill the space, while a mounted TV and comfortable sectional couch create an inviting entertainment area.
Home in Badjeros
4.93 out of 5 average rating, 162 reviews

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Top guest favorite
A sunroom features a mixture of wooden furniture, including a sectional sofa and lounge chairs, arranged around a central table. String lights hanging overhead provide warm illumination, while large windows offer views of the surrounding nature.
Home in Cambridge
4.93 out of 5 average rating, 447 reviews

"Cottage Home On The River" 1 Bedroom

Welcome to Speed Island Trail! Nestled on 1 Acre property in a forested area that backs onto the Speed River. Enjoy Beautiful views all season long with large floor to ceiling windows and wildlife right outside your door. It is just like being out at the cottage. This beautiful one bedroom house is beautifully decorated, has a large kitchen and a breakfast bar. Enjoy the large sunroom and deck where you can sit back and relax. Added bonus the Chickadees eat right off your hand!

Superhost
A cozy living area is visible, featuring a comfortable seating arrangement with a light-colored couch and accent chairs. A fireplace and a large television are positioned against a decorative wall unit. Soft lighting and warm tones create a welcoming atmosphere, complemented by a plush rug on the floor.
Home in Caledon
4.76 out of 5 average rating, 34 reviews

Nordic Style Retreat on 8 Acres w/ Hot Tub

🏆 Named a Guest Favorite! 🏆 Enjoy crisp fall 🍂 evenings on the patio, cozy blankets included ☕️ Unwind on a peaceful 8-acre property just 1 hour from Toronto. • 8 mins from TOC Osprey 🏌️ • Cozy living area with electric fireplace • 2 primary bedrooms with ensuites • Starlink Wi-Fi 🌟 • Smart TV Start your morning on the patio, stroll private & nearby trails, A perfect escape for families, nature lovers, golfers, and anyone seeking a calm, stylish retreat outside the city.

Top guest favorite
Home in Port Dalhousie
4.96 out of 5 average rating, 314 reviews

Lux Lake Ont Beachfront - Fire Pit & Sunset Views

License 23 110691 STR. Enjoy extraordinary sunsets and views of Lake Ontario and the Toronto Skyline while sitting in comfortable Muskoka chairs around a fire pit, enjoying a cup of coffee or a glass of wine. My home offers high-speed internet, multiple Smart HD TVs, indoor fireplace, 2 outdoor fire pits, and a large backyard with stairs leading to a Private Beach. Just a short walk to Lakeside Beach, downtown Port Dalhousie, and a short drive to Niagara wineries!

Guest favorite
The exterior of a two-story house showcases a blend of stone and dark wood siding, with a spacious deck accessible from the upper floor. Lush green grass and neatly arranged flower beds surround the home, while a gray sky sets a calm backdrop.
Home in Alton
4.97 out of 5 average rating, 119 reviews

Cozy Country Spring Getaway | HotTub + Fire Pit

Escape to the countryside this spring 🌸 Unwind in the hot tub, enjoy cozy fires under the stars, and soak in the peaceful charm of Alton. Perfect for a relaxing getaway, girls weekend, or quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

Top guest favorite
A charming entrance is framed by an inviting covered porch, featuring decorative woodwork and a bright yellow door. Lush greenery surrounds the entryway, providing a serene and welcoming atmosphere. A stone path leads toward the door, enhancing the home's inviting character.
Home in Elora
4.97 out of 5 average rating, 877 reviews

Elora Heritage House

Welcome to Elora Heritage House, where unforgettable experiences await in the heart of Elora. Built in the 19th century, our meticulously crafted home exemplifies quality and attention to detail. Discover carefully curated rooms with mid-century furniture, modern design, and a nostalgic ambiance. Nestled amidst serene trees, generous natural surroundings, world-class dining, and shops are just steps away. Embrace the essence of Elora at our cozy haven.

Top guest favorite
A charming yellow house features a wide front porch with wooden seating and a grill. Lush greenery surrounds the porch, enhancing the outdoor space. The entrance is framed by a pair of glass doors flanked by symmetrical windows, inviting guests into the home.
Home in Orangeville
4.95 out of 5 average rating, 108 reviews

Central OVille,3 bed Victorian, walk to Lake, pets

This 3 bedroom (4 beds), 1,500 sqft unit with new Gas Fireplace and central A/C sleeps 6 adults comfortably. Bedroom 1 has a queen-sized bed, another a double bed while Bedroom 3 contains two separate single beds. There is large and beautiful private deck and fenced back yard that contains a full-sized BBQ The unit contains: Washer and dryer (within the unit), hard-wood floors, and free high-speed unlimited internet and HD Cable.

Top guest favorite
The exterior of a century home is highlighted, featuring a welcoming porch surrounded by lush greenery. A paved driveway leads to the entrance, with neatly trimmed grass and decorative landscaping enhancing the inviting appeal.
Home in Paris
4.99 out of 5 average rating, 104 reviews

Paris Oasis-The Maples on Brock

Stay in this immaculately renovated century home, which is just a short walk from downtown Paris and comes with all the perks and white-glove service of a 5 Star Hotel. If you’re searching for the perfect home for your next family vacation, stay-cation, business trip, or long-term rental that satisfies both luxury & location, then look no further. Save your dates now and secure a Paris holiday you’ll always remember!

Popular amenities for Caledon house rentals

When is the best time to visit Caledon?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$13,598 GYDG$12,971 GYDG$12,971 GYDG$14,435 GYDG$14,854 GYDG$15,272 GYDG$15,690 GYDG$16,527 GYDG$15,272 GYDG$14,854 GYDG$13,598 GYDG$13,598 GYD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

Quick stats about house rentals in Caledon

  • Total vacation rentals

    Explore 1,130 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 14,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    410 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    540 properties have a dedicated workspace

  • Wi-Fi availability

    1,080 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

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