
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.

Christie St. Coach House
Located steps from Lake Ontario you will find peace and quiet at the Coach House. One of the best streets to view the sunset over Lake Ontario! A short 10min walk to Port Dalhousie business district and Lakeside Park Beach. Find all you need to eat and drink at several restaurants and cafés. Quick access to the QEW and 406 highways. Centrally located between the Wine Regions of Niagara-on-the-lake and The Bench. 15mins East or West will find you at most Niagara Wineries. Licence No: 23112230 STR

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

"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.

RivertrailRetreat | Unique Deck + Skiing + Theatre
The entire home is exclusively yours during your stay, ensuring complete privacy with no other guests on the premises. Enjoy BBQs on the deck and unwind in the in-ground seating area. Immerse yourself in a cinematic experience with our 11-speaker Klipsch sound system, perfect for movie nights. Book now to unlock discounts at local restaurants and activities in town 2-minute walk to the park and 5 minute drive from Breslau airport
Popular amenities for house rentals in Caledon
House rentals with a pool

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

Year-Round Heated Pool & Hot Tub Family Oasis

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

Entire Guest Unit+Free Parking by Glenbridge Plaza

Heart of Kimberley - with views and a hot tub

The Nautical Nook | Luxury Beach House

Wine country Cottage 15 min drive to old Town NOTL

California Chic +Breathe +Unwind +Restore
Weekly house rentals

Stonewell Farm Guest House

Private Basement Entrance suite

Charming and Peaceful Retreat with Hot Tub

Modern Stay Brampton Luxurious (Basement)

Over the moon basement suite

Spotless 100% Private House ~Trinity Plaza

Luxury 4BR Stay with Swim Spa, Golf & Fireplaces

3BR 3.5WR | RO Water | BR with TV | Workdesk
Private house rentals

Perfect@2, Comfortable @4

Charming Farmhouse Stunning Views & Hot tub

A Private Oasis with Fireplace

3BR Spacious Home - KING BED

Cozy Campbellville

Bright & Spacious 6 BR | Private | Main Floor Bath

Under the Whispering Pines

Trendy & Cozy Retreat 4BR Detached Spacious House
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $84 SGD | $81 SGD | $81 SGD | $90 SGD | $92 SGD | $95 SGD | $97 SGD | $103 SGD | $95 SGD | $88 SGD | $90 SGD | $90 SGD |
| 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 $13 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
1,020 of Caledon holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi 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 pools Caledon
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- Rentals with a firepit Caledon
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- House rentals Peel Region
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Blue Mountain Village
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- CF Toronto Eaton Centre
- Financial District
- Trinity Bellwoods Park
- BMO Field
- Massey Hall
- Casa Loma
- Whistle Bear Golf Club
- Dufferin Grove Park
- Snow Valley Ski Resort
- Rouge National Urban Park
- Royal Ontario Museum
- Christie Pits Park




