House holiday rentals in Caledon

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Top-rated house rentals in Caledon

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Guest favourite
A serene living area is depicted, featuring a spacious bed, a smart TV, and a dining table set for two. Natural light enters through the door, which leads to an outdoor space. Soft carpeting and neutral-colored walls create a calm environment.
Home in Brampton
4.79 out of 5 average rating, 110 reviews

Your Own Suite-Moderncharm Hideaways Near TorAirp

Charming Executive Suite with Large Backyard on Ravine Just minutes away from Toronto International Airport, a variety of amazing restaurants (including authentic Indian cuisine),grocery stores This suite is perfect choice for a weekend getaway, business trip, staycation, work-from-home alternative, or a cozy home base while exploring Toronto best The unbeatable location puts you 24 minutes from Downtown Toronto, 1.5 hours from Niagara Falls. And the breathtaking fall colors of North Country.

Top guest favourite
A bright kitchen is highlighted by clean white cabinetry and open shelving displaying dishware. A central island provides seating for four, with a fruit bowl and a potted orchid as decorative accents. Natural light enters through a window overlooking a landscaped area.
Home in Port Dalhousie
4.99 out of 5 average rating, 161 reviews

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

Guest favourite
A modern living area features a white leather sofa with decorative red pillows, complemented by a wooden coffee table. A small dining table with two chairs is positioned nearby. The kitchen area is visible, showcasing sleek cabinetry and stylish backsplash, with artwork depicting a tranquil forest scene.
Home in Cooksville
4.82 out of 5 average rating, 114 reviews

Cozy Guest Suit in Mississauga

Experience a stylish stay at this well-located spot. The Seprate ground-level 1BR, 1WR, Living and Kitchenette, Along with 1 parking unit is designed for guest privacy and offers easy access to everything. Close to bus stop for Square One, and Cooksville GO station for downtown Toronto. Near the airport and highways, just a 20-minute drive to downtown (non-rush hour). Enjoy proximity to shops and restaurants, between Square One & Sherway Gardens Mall. There are no live TV Channels on the TV.

Top guest favourite
A cozy living area features a plush gray sofa and two bright armchairs, inviting relaxation. Natural light filters through the large windows, illuminating the wooden log walls and earthy decor elements, while a small coffee table sits in the center.
Home in Elora
4.99 out of 5 average rating, 215 reviews

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

Top guest favourite
A dining table is elegantly set with two decorative plates, glasses of varying sizes, and utensils arranged symmetrically. A soft glow is provided by a small candle flickering in a metallic holder, creating a subtle ambiance for mealtime.
Home in Vaughan
4.99 out of 5 average rating, 377 reviews

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.

Top guest favourite
Home in Alton
4.97 out of 5 average rating, 112 reviews

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

Guest favourite
Home in Caledon
4.87 out of 5 average rating, 173 reviews

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!

Top guest favourite
A modern living room is presented with a grey sectional sofa and a plush armchair. Above, a wall clock adorns the light-colored wall, while large windows with soft sheer curtains allow natural light to enter. A small plant sits on a nearby table.
Home in Milton
4.98 out of 5 average rating, 172 reviews

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.

Guest favourite
A sunroom features a mixture of wooden furniture, including a sectional sofa and lounge chairs, arranged around a central table. String lights hanging overhead provide warm illumination, while large windows offer views of the surrounding nature.
Home in Cambridge
4.93 out of 5 average rating, 429 reviews

"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!

Top guest favourite
A brick exterior home is set against a bright blue sky, featuring a manicured front lawn with green grass and white flowers. Large windows allow natural light to illuminate the entrance, where a welcoming white door is positioned. A tree provides shade, enhancing the outdoor space.
Home in Georgetown
4.86 out of 5 average rating, 103 reviews

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!

Top guest favourite
A charming entrance is framed by an inviting covered porch, featuring decorative woodwork and a bright yellow door. Lush greenery surrounds the entryway, providing a serene and welcoming atmosphere. A stone path leads toward the door, enhancing the home's inviting character.
Home in Elora
4.97 out of 5 average rating, 859 reviews

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.

Superhost
A spacious living area showcases a large grey sectional sofa, accented by yellow throw pillows. A sleek coffee table sits in front, with a decorative plant and tray. In the background, a mirrored wall reflects natural light, and a dining area is visible, featuring black chairs and a table.
Home in Malton
4.82 out of 5 average rating, 186 reviews

3 BR 2 WR Entire home 5 Km Toronto Pearson Airport

Welcome to our luxurious 3BR 2 Full Washroom.(The upper portion only) just 5km from Toronto YYZ Airport! Nestled in a central and safe neighborhood, our fully equipped space boasts family-friendly decor, free WiFi, on driveway parking. Close to Go Train, major highways, and convention centers, with quick access to downtown, Lake Ontario, Square One Mall, and Bramalea Mall. . Hosted by a Superhost, your perfect Toronto stay awaits!

Popular amenities for house rentals in Caledon

When is the best time to visit Caledon?

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Avg. price£48£46£46£51£53£54£56£59£54£51£51£51
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°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 £7 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

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