House vacation rentals in Caledon

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Top-rated house rentals in Caledon

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Top guest favorite
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, 159 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

Top guest favorite
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, 209 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 favorite
A modern living area is shown, featuring a pull-out sofa with light trim and a soft area rug. A sleek entertainment unit supports a flat-screen television, while a stainless steel refrigerator is visible in the corner. Natural light enters through a nearby window, partially covered by dark curtains.
Home in Brampton
4.91 out of 5 average rating, 186 reviews

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.

Top guest favorite
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, 365 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 favorite
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 favorite
Home in Caledon
4.86 out of 5 average rating, 162 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 favorite
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, 166 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.

Top guest favorite
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, 426 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 favorite
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, 848 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.

Guest favorite
A modern kitchen features sleek white cabinetry and a large island with seating for four. Stainless steel appliances are visible, including a refrigerator and microwave. Bright lighting fixtures hang above the island, and a small green plant adds a touch of freshness to the countertop.
Home in Oakville
4.97 out of 5 average rating, 115 reviews

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.

Top guest favorite
A floral wall in varying shades of pink is displayed prominently, featuring the words 'The Rose House' in glowing neon. Below the sign, a row of clear glasses rests on a light-colored shelf, inviting guests to enjoy a toast.
Home in Niagara-on-the-Lake
4.98 out of 5 average rating, 299 reviews

The Rosé House NOTL - Glam room - Old Town

Welcome to the The Rosé House located in the heart of NOTL. This newly renovated 3100sqft home is the perfect to celebrate a mature Girl's Getaway! Bring your friends/family to enjoy everything NOTL has to offer! Steps to wineries, the Pedal Pub, golf courses, the lavender farm, Ice Wine Festival, restaurants, shopping, Shaw Festival Theatre and more! Niagara Falls is also within easy reach!

Guest favorite
A neatly arranged bedroom features a decorative, patterned bedspread on a spacious bed. Two bedside tables with lamps are placed on either side. The wall displays a dreamcatcher design and an uplifting message, contributing to a calming atmosphere. Natural light enhances the inviting space.
Home in Richmond Hill
4.92 out of 5 average rating, 198 reviews

20%OFF| 0 Cleaning Fee| Mins to Lake| Free Parking

❥ Transportation: 🚗 5 mins to Highway 404. 🎢 20 mins to Wonderland; ✈️ 40 mins to airport. ⛳ 7 mins to Golf. ❥ Privacy: 🅿️ Driveway parking. 🌙 No sidewalks for added quiet. ❥ Amenities: 🛒 Close to Food Basics, No Frills, and 🥢 15 mins to T&T. ❥ Recreation: 🛶 Near Lake Wilcox (boating), 🏊 5 mins to Oak Ridges Center, 🌊 10 mins to Lake Wilcox & Bond Lake, 🥾 hiking trails nearby.

Popular amenities for Caledon house rentals

When is the best time to visit Caledon?

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Quick stats about house rentals in Caledon

  • Total vacation rentals

    Explore 1,060 vacation rentals in Caledon

  • Nightly prices starting at

    Caledon vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

  • Verified guest reviews

    Over 14,430 verified reviews to help you choose

  • Family-friendly vacation rentals

    410 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Vacation 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 vacation rentals include wi-fi 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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