
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

Bright 1BR Apartment for 2 · Richmond Hill
Bright and private walk-out basement apartment in a safe, quiet neighborhood in Richmond Hill. This self-contained unit is ideal for up to 2 guests and features a private entrance, a bedroom with a queen-size bed, a cozy living area with a sofa bed, and a full kitchen with basic cookware and a large double-door refrigerator. Enjoy Netflix, high-speed internet, and easy access to Highway 404, supermarkets, and restaurants. The price includes accommodation for up to 2 guests. No extra guest fees

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.

Cozy Cabin Vibes - Hot Tub• Firepit• Snowy Retreat
Escape to our riverside cabin this winter—soak in the hot tub under falling snow, curl up by the fire, and enjoy cozy evenings surrounded by nature. Perfect for couples, families, a ski weekend away, girls’ weekends, or a 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

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!

5 Km to Toronto Pearson Airport, sleeps 3 /4
Tastefully decorated , well maintained , cozy , luxurious 5 Km to Pearson Airport. 25 minutes to Union Station. downtown Toronto Lakeshore in Malton, Mississauga.Breakfast kitchen , large TV , Netflix , prime sleeps 3 , One free guest parking . 3 Km to Malton GO Station, 5 km to airport 10 min to International Centre. Toronto Congress Center. Woodbine Casino. Close to all Highways, Square One shopping mall. Well connected by public transport. Ride-sharing facilities in plenty.

"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!

Halton Hills Hideaway_Private Suite
🌿 Halton Hills Hideaway – Cozy Basement Suite Near Downtown Georgetown ✨ What You’ll Love: 🚪 Private Basement Suite – Separate entrance & no shared areas 🛏️ Queen Bed – Comfy and perfect for solo travelers or couples 🌳 Garden Views – Enjoy calming green views from your lookout window 🧼 Clean & Cozy – Thoughtfully prepared for a peaceful stay 🏘️ Charming Neighborhood – Quiet, friendly, and safe 🔍 Check the amenities section for full details—we’d love to host you!

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.

Elegant 2BR townhouse condo in central Oakville
Enjoy your stay in this elegant, clean, and fully equipped two bedroom and two-bathroom condo townhouse. Centrally located in Oakville and within walking distance to shops, restaurants, and parks. Beautiful upscale building in a quiet and safe neighborhood with large terrace overlooking a mature tree lined street. Abundant walking trails nearby for you to explore and enjoy. Easy access to highway 407, 403, QEW and Trafalgar GO Station.
Popular amenities for Caledon house rentals
House rentals with a pool

newly renovated, close to airport, washer/dryer

Seraya Wellness Retreat

Luxury 4BR Oasis Year Round Heated Pool & Hot Tub

Cheerful 3 Bedrooms Available for Renting!

Entire Guest Unit+Free Parking by Glenbridge Plaza

Primrose Park

California Chic +Breathe +Unwind +Restore

Modern Custom Built Walkout to Marble Pool Game RM
Weekly house rentals

Entire Unit, clean and Private 1 bdr

Private Basement Entrance suite

Live Lavishly: Modern Studio, 5G, Parking

Cozy Townhouse Near Pearson & Wedding Venues

Spacious 4BR Home Near Wedding Venues|Free Parking

Pond View Gardens

Entire Lower Level Home 3500 Sq Walk Out

100% Private BrandNew 4 Bedrooms 2 king Size beds
Private house rentals

Stunning Luxury Home

Perfect@2, Comfortable @4

Modern Stay Brampton Luxurious (Basement)

Adey's Haven: 1BR + Free Parking

3BR Spacious Home - KING BED

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

Brampton Retreat with Basement

Stylish 5-Star 2BD,2BA|Hwy 404|Pearson Airport
When is the best time to visit Caledon?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $107 NZD | $103 NZD | $103 NZD | $114 NZD | $117 NZD | $121 NZD | $124 NZD | $131 NZD | $121 NZD | $117 NZD | $107 NZD | $107 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 1,120 holiday rentals in Caledon

Nightly prices starting at
Caledon holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 14,650 verified reviews to help you choose

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

Pet-friendly accommodation
Find 160 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
510 properties have a dedicated workspace

Wi-Fi availability
1,090 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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- Family-friendly rentals Caledon
- Rentals with pools Caledon
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Blue Mountain Village
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- BMO Field
- Nike Square One Shopping Centre
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Snow Valley Ski Resort
- Financial District
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Lakeridge Ski Resort
- Beaver Valley Ski Club




