House holiday rentals in Caledon

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Quick stats about house rentals in Caledon

Total holiday rentals
Explore 1,100 holiday rentals in Caledon
Nightly prices starting at
Caledon holiday rentals start at €9 per night before taxes and fees
Verified guest reviews
Over 15,070 verified reviews to help you choose
Family-friendly holiday rentals
420 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 170 rentals that welcome pets
Holiday rentals with a pool
50 properties feature pools
Rentals with dedicated workspaces
510 properties have a dedicated workspace
Wifi availability
1,050 of Caledon holiday 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 house rentals in Caledon

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

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Top guest favourite

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

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

4.99 out of 5 average rating, 180 reviews

Top guest favourite

Home in Alton

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

5.0 out of 5 average rating, 29 reviews

Top guest favourite

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

Orangeville 3BDRM House

This home can accommodate an escape from the city to relax/explore or offer a quiet place to work or recharge if on a business trip. This clean & cozy townhouse is perfect for the whole family. Enjoy a full kitchen stocked with coffee, sugar, honey & spices. The dining area sits 4 with some bonus additional seating at the nearby island. The living room has a large couch with 2 additional seating options that have a clear view of the television. There are 3 fantastic spacious bedrooms.

4.94 out of 5 average rating, 53 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!

4.86 out of 5 average rating, 273 reviews

Superhost

Home in Erin

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.

4.75 out of 5 average rating, 32 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.

4.73 out of 5 average rating, 45 reviews

Guest favourite

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

Cozy Country Spring Getaway | HotTub + Fire Pit

Escape to the countryside this spring 🌸 Unwind in the hot tub or pool, 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

4.96 out of 5 average rating, 130 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.

4.93 out of 5 average rating, 86 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!

4.91 out of 5 average rating, 22 reviews

Guest favourite

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

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.

4.93 out of 5 average rating, 120 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.

5.0 out of 5 average rating, 17 reviews

Top guest favourite

A charming log cabin is set amidst lush greenery, featuring a covered porch with decorative plants. The building showcases a symmetrical roof and multiple windows, allowing natural light to fill the interior. The stone pathway winds through the manicured lawn, enhancing the serene outdoor setting.

Home in Kleinburg

Charming Log Home - 25 private acres in Caledon

Our home sits on the rolling hills of Caledon East surrounded by a serine ambiance of pure peace and quiet. Just 45 minutes from the GTA where you can make memories w/family and friends. Take a walk though the trails, enjoy sitting by the pond, or enjoy skating or snow shoeing during the winter months. We welcome all our guest(s) to take a deep breath, inhale peace and exhale happiness.

4.99 out of 5 average rating, 82 reviews