
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.

The Heart of New Hamburg - Picturesque Modern Home
This newly renovated schoolhouse doubles as a picturesque live-in museum! Well lit with stately windows, the upper level delivers a fusion of classic and modern with a fully equipped kitchen, master bedroom and large bathroom with a quaint tub and hand crafted fittings. The lower level boasts of 2 bedrooms with bathrooms, a cozy living area, kitchenette, dedicated workspace and separate entrance. The back patio has heated flooring; making the winter months bearable for outdoor activities.

Country Living in The Heart of Niagara on the lake
***NEW HOT TUB FOR 2024 SEASON This completely renovated private home is located in the heart of Niagara wine country just a few kilometers from the Old Town of Niagara on the lake. You can relax in the large backyard overlooking the vineyards or have your morning coffee on the front porch. Enjoy a nice dinner out on the new patio, relax by the fire at night in your adirondack chairs or soak in the hot tub. We have it all! 3 Night Minimum on weekends from June 15-Oct15 and all holiday weekends

Waterfront Niagara-On-The-Lake Vineyard Farmhouse
Experience this dreamy farmhouse with stunning seasonal vineyard and waterfront views, nestled between the Niagara River and Inniskillin Winery. Enjoy stylish contemporary interiors, a cozy gas fireplace, and a clawfoot tub. Perfectly located by top vineyards and Niagara trail, minutes from historic Old Town, this 3-bed, 3-bath retreat is ideal for group getaways, bridal parties, and special occasions. *Weddings view Property Description IG/TT: @willowfarmhousenotl NOTL STR License No. 079-2022

"Clement House" a Restored Residence built in 1786
Welcome to this fully renovated house originally built in 1786 by Joseph Clement, the only non-stone home to survive the burning of St Davids in 1814. Backing onto the award-winning Ravine Vineyard Estate Winery, The Clement House sits along the grapevines featuring a large patio and two-person swing. Located on the Niagara Escarpment, you are 15 minutes from Old Town Niagara-On-The-Lake and 18 minutes from Niagara Falls. Licensed by the Town of Niagara-on-the-Lake. License number 044-2023.

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.

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!

"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!

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

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

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

Private NOTL Retreat • Pool • Quiet Escape

Ravine Paradise ! heated pool and hot tub!

Entire Guest Unit+Free Parking by Glenbridge Plaza

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

Wine country Cottage 15 min drive to old Town NOTL

California Chic +Breathe +Unwind +Restore

Boutique Wine Country Home with Pool and Hot Tub
Weekly house rentals

Spacious 4BR House | Golf • Spa • Private & Serene

Stunning Luxury Home

Woodland River Retreat With Hot Tub

Charming and Peaceful Retreat with Hot Tub

Luxury Hockley Estate Spa

3BR Spacious Home - KING BED

The Urban Nest

#1 Best Deal in Brampton
Private house rentals

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

Private river access with pool, canoes, kayak

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

Cottage/Farm House for Stay/ Events and Weddings

Charming Farmhouse Stunning Views & Hot tub

Place to Relax with whole Family

Charming retreat with lake view

Lovely Family Retreat | Near Crawford Lake +Trails
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $83 SGD | $83 SGD | $78 SGD | $88 SGD | $91 SGD | $93 SGD | $96 SGD | $101 SGD | $93 SGD | $91 SGD | $83 SGD | $83 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 1,130 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 14,140 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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- 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
- Harbourfront Centre
- Distillery District
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Downsview Park
- Snow Valley Ski Resort
- Financial District
- Wilfrid Laurier University
- Massey Hall
- Casa Loma
- Dufferin Grove Park





