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Caledon holiday lettings

We found 611 holiday rentals — enter your dates for availability

Discover a selection of 44 homes and other holiday rentals in Caledon that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as air conditioning and Wi-Fi. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Caledon

Showing deals for:7 Nov - 14 Nov
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Why visit Caledon

  • Picturesque Nature Reserves: Caledon boasts stunning nature reserves perfect for hiking, birdwatching, and enjoying the great outdoors.
  • Charming Caledon Village: Experience the warmth of friendly locals and explore the quaint shops and cafes in Caledon Village.
  • Outdoor Activities: Engage in a variety of sports and recreational activities that cater to both thrill-seekers and families.
  • Diverse Accommodation Options: Choose from a range of holiday rentals, including cosy cottages and spacious homes for your stay.
  • Cultural Events: Attend various cultural activities and events showcasing the vibrant community spirit of Caledon.

Popular types of accommodation in Caledon

Caledon offers a delightful selection of holiday rentals, including houses, apartments, and cosy cottages. Whether you're seeking a charming cabin retreat or spacious house rentals for the whole family, you'll find the perfect base for your adventures. With various options like holiday cottages and condo rentals, there's something to suit every traveller's needs. Discover the beauty of Caledon and make lasting memories in your ideal accommodation.

  • Houses: The top choice for many visitors to Caledon, offering spacious and comfortable living ideal for families, friends, or couples.
  • Apartments: A popular selection, providing a convenient and self-contained option for those seeking a city feel during their stay.
  • Condos: These modern accommodations offer a blend of luxury and practicality, perfect for a stylish getaway.
  • Cabins: A delightful option for those wanting to immerse themselves in nature with a rustic charm.
  • Villas: These upscale residences provide a lavish experience for travellers looking for extra comfort and amenities.**

Top attractions in and around Caledon

Caledon is an idyllic destination for outdoor enthusiasts and adventurers, offering a range of activities for sports lovers and families alike. Visitors can explore picturesque nature reserves, vibrant urban parks, and event venues that host various cultural activities. Whether you're seeking a tranquil escape or an action-packed holiday, Caledon promises an enriching experience for all types of travellers.

  • Belfountain Conservation Area: A serene natural reserve in Caledon, featuring picturesque trails, stunning waterfalls, and a charming historic bridge, perfect for leisurely hikes and picnics.
  • The International Centre: Located 9.3km from Caledon, this dynamic civic venue hosts a variety of events with a welcoming atmosphere, making it a hub for community gatherings and exhibitions.
  • Alton Mill Arts Centre: Nestled in Caledon, this vibrant arts centre showcases local talent through galleries and studios, offering a rich cultural experience amidst beautiful surroundings.

Things to do recommended for couples

Ready for a romantic getaway in Caledon? Treat yourselves to the luxurious ambiance of Caledon Country Club, indulge in a fun round at Putting Edge Mississauga, or hit the slopes at Caledon Ski Club for an adventurous day together. Enjoy every moment in this charming destination!

Things to do recommended for families

Families will delight in the stunning Cheltenham Badlands, perfect for relaxation, or have a splashing good time at Wet 'n' Wild Toronto, an exhilarating waterpark only 8.1km away. For some indoor fun, visit Century Gardens Arena, located 6.8km from Caledon, offering wellness and recreation.

Things to do recommended for groups

Groups visiting Caledon can indulge in retail therapy at Vaughan Mills Mall, enjoy a round of golf at the scenic Osprey Valley Golf course, and explore local produce at Downey's Farm Market for a taste of the region's charm.

What do I need to keep in mind when booking a vacation in 'Caledon

If you're travelling with a group, with family, bringing your pets along, or seeking extended stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Caledon with a group: Think about how many bedrooms you require, as well as features like a fully-equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily refine your search for all these options, and more, on Vrbo.
  • Traveling to Caledon with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Caledon: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Caledon: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Caledon

Caledon, Ontario, offers a delightful blend of adventure and relaxation, perfect for outdoor enthusiasts and families alike. Explore the charming Caledon Village, set against an idyllic rural backdrop, where friendly locals create a warm atmosphere. Whether you seek luxury or budget-friendly experiences, the countryside invites you to unwind in its beautiful locations. Enjoy sports and outdoor activities while soaking in the picturesque surroundings of this charming countryside gem.

  • Brampton: Located 5.6km from Caledon, Brampton is a vibrant city known for its family-friendly atmosphere and bustling urban life. Visitors can indulge in a variety of experiences, from shopping at the massive Bramalea City Centre to enjoying the thrills of the local amusement parks. Brampton also boasts several landmarks, including a popular theme park and a waterpark, making it an ideal destination for families. With its lively stadium hosting various events, Brampton offers a perfect blend of city excitement and entertainment.
  • Vaughan: Situated 11.2km from Caledon, Vaughan is a dynamic city that caters to both families and business travellers. The city is renowned for its attractions, including the famous Vaughan Mills shopping centre and exciting amusement parks. Vaughan is also home to impressive landmarks like a large theme park and a state-of-the-art sports facility stadium, ensuring there’s always something to do. Whether you're looking to shop, dine, or enjoy thrilling rides, Vaughan provides an excellent urban experience with plenty of options for leisure and entertainment.
  • Bolton: Nestled within Caledon, Bolton is a charming village that offers a delightful mix of family-friendly activities and outdoor adventures. Visitors can explore local shopping centres and enjoy the nearby amusement parks, while the village’s parks provide a serene escape into nature. Bolton is an excellent spot for those seeking a quieter experience, with its easy access to beautiful landscapes and recreational areas. Its close-knit community and picturesque surroundings make Bolton a lovely destination for a relaxing getaway.

Best time to go to Caledon

If you're planning a trip to Caledon, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.9°F (-6.7°C)Light RainMostly CloudyAverageAverage
February20.5°F (-6.4°C)Light RainMostly CloudyAverageSlightly Low
March30.0°F (-1.1°C)Light RainMostly CloudyAverageSlightly Low
April41.0°F (5.0°C)Light RainMostly CloudyAverageSlightly Low
May54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
June62.4°F (16.9°C)Light RainMostly SunnySlightly HighSlightly High
July68.0°F (20.0°C)Light RainMostly SunnySlightly HighSlightly High
August66.7°F (19.3°C)Light RainMostly SunnyAverageSlightly High
September60.3°F (15.7°C)Light RainMostly SunnySlightly HighAverage
October48.2°F (9.0°C)Light RainMostly CloudySlightly LowAverage
November36.3°F (2.4°C)Light RainMostly CloudySlightly LowAverage
December27.7°F (-2.4°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can often lead to significant savings, as prices can vary. Additionally, booking a longer stay typically allows for even greater discounts. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a handy platform for you to plan new trips, resume previous ones, or manage your travel arrangements. You'll be able to see the properties you've saved or booked neatly organised into categories: Potential, Upcoming, or Current Trips. To begin making the most of Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the lush setting in Caledon

The countryside, waterfalls and forests are the perfect backdrop to your holiday home in Caledon. This city's golfing, horse riding and spas draw many visitors. Canada's Wonderland and Vaughan Mills Mall are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Caledon

Are you hoping to find attractions to visit while you're in town? Venture out of your holiday home and experience everything that makes Caledon a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Canada's Wonderland (16.5 mi / 26.6 km)
  • Albion Hills Conservation Area (6.7 mi / 10.8 km)
  • Osprey Valley Golf (8.5 mi / 13.6 km)
  • Copper Creek Golf Club (11.7 mi / 18.8 km)
  • Hockley Valley Resort (12.9 mi / 20.8 km)
  • Wet 'n' Wild Toronto (13.3 mi / 21.4 km)

Exploring the natural landscape of Caledon

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Caledon is a great spot to appreciate mother nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Cheltenham Badlands (5.5 mi / 8.9 km)
  • Albion Hills Conservation Area (6.7 mi / 10.8 km)
  • Belfountain Conservation Area (7.3 mi / 11.8 km)
  • Terra Cotta Conservation Area (9 mi / 14.4 km)
  • Island Lake Conservation Area (12.2 mi / 19.6 km)
  • Centennial Park (19 mi / 30.7 km)

How to get to and around Caledon

The nearest airport is in Toronto, ON (YYZ-Pearson Intl.), located 16.9 mi (27.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Toronto, ON (YTZ-Billy Bishop Toronto City), which is 27.8 mi (44.7 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Caledon?
Based on our research, houses are the most sought-after holiday property type in Caledon. But that goes without saying, everyone's idea of an awesome stay can differ. Vrbo has holiday rentals of all sizes, shapes and budgets, and we'll help you locate your ideal match.
How much does it cost to rent a holiday rental in Caledon?
The average price for a holiday rental in Caledon can vary based on factors such as property type, length of stay and season. Whether you're dreaming about a sprawling house with room for friends and family or an apartment for just you and the kids, just add your travel dates to see some great-value stays.
How much does it cost to rent a beach house in Caledon?
When you travel and the style and size of the property will help determine the cost of your beachside escape. Put in your Caledon travel dates to view your options on Vrbo. Can't live without a private pool? Use our filters to select the features and amenities you need.
Are there pet-friendly holiday rentals in Caledon?
Yes. You can pick from 12 holiday rentals that cater to pets in Caledon. Lots of our pet-friendly holiday rentals even come with an outdoor space for your fur child to have fun in, complimentary treats, doggie beds and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect digs on Vrbo.
Can I rent a house with a pool in Caledon?
Add an extra layer of fun to your trip by booking your family into one of the two houses with a private pool in Caledon. Use our handy search filter to find the kind of property you want on Vrbo, and then spend lazy days splashing about in a swimming pool that's just for you.
What are popular rental amenities in Caledon?
When it comes to rental amenities that guests look for in Caledon, a barbecue grill, a garden and ski-in/ski-out facilities are the most popular. With Vrbo holiday rentals, you'll find options to match your style and taste, whether you're on a trip with friends, relatives or even pets.
Are there large group holiday rentals in Caledon?
Take your pick of six Vrbo holiday properties in Caledon that can sleep five or more people. You'll enjoy all the space and privacy you need to hang out with your loved ones — and nobody else.
Are there holiday rentals in Caledon that welcome kids?
Gather your entire family for an epic adventure in Caledon at one of our 12 family-friendly holiday rentals. Lots of these stays feature amenities that are just perfect for trips with the little ones, such as laundry facilities, multiple bedrooms and entertainment units. Simply click on the "Properties good for families" filter and pick out your favourite.
What are the top attractions for families in Caledon?
Keeping the kids amused during your stay in Caledon is a breeze with these fabulous family-friendly attractions:

  • Caledon Equestrian Park
  • Albion Hills Conservation Area
  • Cheltenham Badlands

Are there one-bedroom holiday rentals in Caledon?
Yes, you can pick from three one-bedroom rentals in Caledon. Whether you're looking for a townhouse or a fancy condo, Vrbo's one-bedroom properties are just right if you don't need tons of space. One of the main perks of having your own pad? You'll never need to share your trip with strangers.
Can I find two-bedroom holiday rentals in Caledon?
Gather your besties and enjoy a relaxing escape in one of the two two-bedroom holiday rentals Caledon has to offer.
Are there holiday rentals with WiFi in Caledon?
You'll find seven holiday rentals with WiFi in Caledon. If you'd like to disconnect from daily life during your trip, but still want to be connected to the internet, these properties have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Caledon?
Caledon has nine holiday rentals where you can relax and recharge in air-conditioned comfort. To find a property on Vrbo offering this amenity, enter your preferred travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Caledon?
The minimum required age is normally 16, 18 or 21. It can change from property to property on Vrbo, so check the rules of your preferred Caledon stay before booking.
How long can I rent a holiday rental in Caledon for?
It really depends on the Caledon property. To see a list of options offering extended stays, just enter your dates and number of guests into Vrbo. Look forward to having the whole place to yourself, along with comforts such as a fully-equipped kitchen and a yard where the kids can run and play. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.

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