House vacation rentals in Caledon

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Top-rated house rentals in Caledon

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Guest favorite

Home in Brampton

4.93 out of 5 average rating, 156 reviews

Entire Place 10 mins from Pearson Airport +Parking

Kick back and relax in this calm, stylish space. This listing is located on the border of Vaughan and Brampton, 10 min drive from the airport! 2 min drive to the nearest Grocery store 2 min drive to Shoppers Drug Mart 2 min drive to Starbucks 3 min drive to McDonald’s 4 min drive to Tim Horton’s 5 min walk to the nearest biking trail 7 min drive to Walmart 10 min drive to Toronto Pearson Airport 17 min drive to Vaughan Mills 20 min drive to Yorkdale Shopping Centre 30 min drive to the CN Tower

Guest favorite

Home in Brampton

4.92 out of 5 average rating, 149 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

Home in Vaughan

4.99 out of 5 average rating, 291 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.

Guest favorite

Home in Caledon

4.91 out of 5 average rating, 79 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!

Guest favorite

Home in Badjeros

4.94 out of 5 average rating, 108 reviews

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Guest favorite

Home in Cambridge

4.93 out of 5 average rating, 390 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!

Guest favorite

Home in Orangeville

4.89 out of 5 average rating, 85 reviews

Stylish 3 Bedroom Getaway in Orangeville

Nestled among tree sculptures and lakes, just steps away from downtown and minutes from the serene beauty of Island Lake Conservation Area. Our urban oasis is complete with a comfortable bed, fully equipped kitchen, chic living area, and private balconies. Be transported through time as you wander the streets of downtown, admiring vintage architecture and vibrant culture. Experience the magic of nature and city living combined in one unforgettable stay!

Guest favorite

Home in Grey County

4.97 out of 5 average rating, 133 reviews

The Post Office Motel Boutique

Where luxury and style meet relaxation! The Post Office Motel is a boutique experience with all the luxuries of a day at the spa in peacefully designed space intended to send you straight into vacation mode. Step out of your car and right into the cutest hidden gem of a town known as Kimberley. Located steps to TWO undeniable restaurants, run by top chefs; Justin’s Oven & Hearts Tavern. Georgian Trail at your door step, 20 min to Blue Mtn, 15 min to Thornbury

Superhost

Home in Caledon

5 out of 5 average rating, 4 reviews

Mono Mills Home next to the County Great Getaway

We are located in quiet hamlet of Mono Mills, which is 8 miles to Palgrave and 16 miles to Erin. Orangeville / Caledon area, Ontario, Mono Village. Just Off Airport Rd and Hwy9 area. Cute and Cozy. Sleeps 2-3 people. $1575++ per week, Monthly discounts. Non Smoking. Clean, comes with all linens, utensils, pots/pans, BBQ, Large TV, Cable and Internet. Weekly or Monthly Only. This property is a brand new self-contained In-law suite. airbnb.ca/h/monomills

Guest favorite

Home in Brampton

4.97 out of 5 average rating, 60 reviews

Studio Apartment in Basement

Welcome to the luxury and cozy redefined basement. This exquisite space is designed to elevate your lifestyle and provide unmatched comfort and style. Less than a minute walk to bus stop, 10 minutes to go station and bus terminal, 5 minutes plaza includes; banks, supermarkets, dollar store, 5 minutes to Indian grocery store, 10 min to Walmart, 30 minutes to Pearson Airport. 1 queen bed Sleep 2 Peaceful space, not meant for parties or events.

Top guest favorite

Home in Caledon

4.96 out of 5 average rating, 24 reviews

Caledon Place - Summer Booking Up Fast !

Renovated in 2024. Caledon Place sleeps 8+ for an extended family vacation retreat! Complete with modern decor, 4 bedrooms, a fully stocked kitchen, Xbox One and PS5 video game station for kids and adults, 500 square foot deck for summer lounging, available ethernet port, Wi-Fi throughout and a Tesla Universal EV charger avail for any type of EVs. The unit is the upstairs living space in a single detached home.

Top guest favorite

Home in Kleinburg

4.98 out of 5 average rating, 51 reviews

Charming Log Home - 25 private acres in Caledon

Our home sits on the rolling hills of Caledon East surrounded by a serine ambiance of pure peace and quiet. Just 45 minutes from the GTA where you can make memories w/family and friends. Take a walk though the trails, enjoy sitting by the pond, or enjoy skating or snow shoeing during the winter months. We welcome all our guest(s) to take a deep breath, inhale peace and exhale happiness.