
House holiday rentals in Caledon
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Top-rated house rentals in Caledon
Guests agree: these houses are highly rated for location, cleanliness and more.

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

Secret Garden Cottage Old Town Niagara-on-the-Lake
The Secret Garden Cottage is a charming home situated right in the Historic Old Town of NOTL. In any season, enjoy the entire house AND the gifts that this beautiful area has to offer: Walk or cycle to the many high-quality wineries, outstanding restaurants, charming shops in town, and highly-acclaimed Shaw Festival productions. Or cozy up with all of the comforts of home, enjoying a glass of local wine on the back deck or in the Garden Room, while gazing out over the stunning Secret Garden.

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.

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!

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.

"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!

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.

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

Shades Mill Lake - Unit 1 of 2. 3rd Bed available.
LIKE NOTHING ELSE in Cambridge or K-W! • FREE 4 elongated tubes to use in season • FREE Coffee & Tea • Top 1% airbnb bookings • Luxurious Bath Robes • 12km of Trails in Shades Mill Conservation Area • Living, dining, family room, 2 bedrooms & 2 full bath • FAST WIFI, Free Netflix, AC • Cottage life 4km south of 401 Cambridge Mill 3km 1 acre property with 1 Airbnb unit & owner's part time home Love Nature you'll ♥ it here

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.

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.

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 house rentals in Caledon
House rentals with a pool

Fifa Country Family Getaway with Pool and Trails

Luxury House with a Bright Sunroom & a heated pool

Private river access with pool, canoes, kayak

Ravine Paradise ! heated pool and hot tub!

Luxury Hockley Estate Spa

Entire Guest Unit+Free Parking by Glenbridge Plaza

California Chic +Breathe +Unwind +Restore

Chic King West Studio – FIFA at Your Door
Weekly house rentals

Relaxing Home Away From Home

Cottage/Farm House for Stay/ Events and Weddings

4BR Ultra-Modern Retreat – Fully Renovated & Chic!

Charming Farmhouse Stunning Views & Hot tub

Live Lavishly: Modern Studio, 5G, Parking

Place to Relax with whole Family

3BR Spacious Home - KING BED

#1 Best Deal in Brampton
Private house rentals

Vineyard Estate by the River with Pool!

Royal Beach Lake House & Spa w/ Hot Tub & Sauna

Unwind & Explore at Hockley Valley Coach House

Renovated 3-BR Home Near Old Baldy | BBQ & Hot Tub

Waterfront Niagara-On-The-Lake Vineyard Farmhouse

Entire Lower Level Home 3500 Sq Walk Out

Wedding & Group | 4-BR | Spacious-Elegant-Private

City Escape-Cottage by the Lake
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £48 | £46 | £46 | £51 | £52 | £54 | £55 | £58 | £54 | £52 | £48 | £48 |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about house rentals in Caledon

Total holiday rentals
Explore 1,130 holiday rentals in Caledon

Nightly prices starting at
Caledon holiday rentals start at £7 per night before taxes and fees

Verified guest reviews
Over 14,140 verified reviews to help you choose

Family-friendly holiday rentals
410 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 150 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
540 properties have a dedicated workspace

Wifi availability
1,080 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

Nearby attractions
Caledon’s top spots include SilverCity Brampton Cinemas, Landmark Cinemas 7 Bolton and Uptown Theatre
Destinations to explore
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- Rentals with a firepit Caledon
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- Guest house rentals Caledon
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Blue Mountain Village
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Distillery District
- Harbourfront Centre
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Snow Valley Ski Resort
- Financial District
- Wilfrid Laurier University
- Massey Hall
- Downsview Park
- Casa Loma
- Dufferin Grove Park




