
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.

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

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

Cozy newly renovated one bedroom apt
Bring the entire family to this wonderful location with plenty of space for relaxation. The Toronto Pearson International Airport is only 22 minutes away, and major highways are nearby. A family-friendly setting, side entrance, convenient location, and walking distance to SilverCity Cinemas, Metro Supermarket, TD Bank, CIBC Bank, and a number of restaurants (including MOntanas BBQ & Bar, Hakkalious, Brar's, and others), as well as a number of clothing stores, and many more establishments.

Adorable — One Bedroom Guest Unit in Vaughan, ON
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!

Spacious and Comfy 2 BR Suite
Discover tranquility in our 2-bedroom legal basement apartment, nestled in Milton’s quiet and peaceful neighborhood. Enjoy an open-concept living room with 8.5 ft ceiling, and 2 roomy bedrooms; perfect for couples or families to relax in this comfortable, private, retreat. Easy access to Oakville, Burlington, Mississauga, and Toronto Pearson Airport, and minutes away from Toronto Premium Outlets, Mattamy Cycling Centre, and scenic trails, makes this location ideal for both work and play.

Stylish 3BR | Hot Tub • Firepit • Cozy Fall Escape
Welcome to your relaxing escape in the heart of Alton—a cheerful and spacious 3-bedroom, 1.5-bathroom home backing onto the beautiful Credit River. Perfect for families, friend groups, wedding guests, or anyone craving peace, nature, and comfort. • 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

A Modern 3 Bedroom Home with Free Parking & Wifi
Welcome to our modern 1000sf single-story bungalow in the charming town of Orangeville. Thoughtfully designed for comfort and convenience, this bright and stylish space offers a peaceful retreat just minutes from the vibrant shops, restaurants, and cafes along historic Broadway. Whether you're here to explore the scenic trails at Island Lake Conservation Area, enjoy the local arts scene, or simply relax in a cozy, well-appointed home, this bungalow is the perfect base for your stay.

"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!

Cheerful Private Studio House
Bring yourself to this excellent place for a peaceful family-friendly stay. The Place is near YYZ Toronto Airport, the Go Train station for downtown Toronto, and walking to food outlets, Cassie Campbell Community Centre. Our Place is highly sought-after and has top-rated reviews by our guests. The place is warm and well-lit to provide you cozy comfortable stay. Ensuite private bathroom, walk-in closet, modern kitchenette with dining island space. spacious exercise and yoga area.

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.
Popular amenities for Caledon house rentals
House rentals with a pool

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Luxury Family Oasis W/ GameRoom/King Bed/Hot Tub

Ask re: FALL Specials-Heated Pool-tub Open 365 Day

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

Entire Guest Unit+Free Parking by Glenbridge Plaza

The Nautical Nook | Luxury Beach House

Wine country Cottage 15 min drive to old Town NOTL

California Chic +Breathe +Unwind +Restore
Weekly house rentals

Elegant & Spacious 1 Bd1Bth Private Apmt by Forest

Modern Lakefront Cottage In The City With Hot Tub

Live Lavishly: Modern Studio, 5G, Parking

Newly Renovated Cozy One Bedroom Basement APT

LUXE by Marvalous 2

Cozy Campbellville

3BR 3.5WR | RO Water | BR with TV | Workdesk

Luxurious 5 Bedroom Estate on 2 Acres
Private house rentals

Stonewell Farm Guest House

Private Basement Entrance suite

2 Bedroom Basement Apartment with Modern Amenities

Family Stay | Pool Table | Main Floor Bath & Sleep

Over the moon basement suite

Spotless 100% Private House ~Trinity Plaza

3BR Spacious Home - KING BED

Cozy Townhouse Near Pearson & Wedding Venues
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $116 NZD | $110 NZD | $110 NZD | $123 NZD | $126 NZD | $130 NZD | $133 NZD | $140 NZD | $130 NZD | $121 NZD | $123 NZD | $123 NZD |
| 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 1,060 holiday rentals in Caledon

Nightly prices starting at
Caledon holiday rentals start at $18 NZD per night before taxes and fees

Verified guest reviews
Over 14,430 verified reviews to help you choose

Family-friendly holiday rentals
410 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 150 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
500 properties have a dedicated workspace

Wi-Fi availability
1,020 of Caledon holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Caledon rentals

4.6 Average rating
Caledon stays receive an average rating of 4.6 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 breakfast Caledon
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- Rentals with a washing machine and dryer Caledon
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- Pet-friendly rentals Caledon
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- Rentals with a hot tub Caledon
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Blue Mountain Village
- Distillery District
- Metro Toronto Convention Centre
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- Financial District
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- BMO Field
- Massey Hall
- Casa Loma
- Whistle Bear Golf Club
- Dufferin Grove Park
- Rouge National Urban Park
- Snow Valley Ski Resort
- Royal Ontario Museum
- Christie Pits Park




