Caledon holiday rentals

We found 706 holiday rentals — enter your dates for availability
Discover a selection of 51 homes, 10 apartments 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:30 Oct - 6 Nov

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Why visit Caledon

  • Scenic Natural Reserves: Enjoy picturesque landscapes and extensive trailways that highlight the natural beauty of Caledon, Ontario.
  • Outdoor Adventure: Explore the Caledon Trailway and Forks of the Credit Provincial Park for a mix of adventure and relaxation.
  • Cultural Exploration: Immerse in local culture and history within charming neighbourhoods like Caledon East and Cheltenham.
  • Family-Friendly Activities: Engage in a variety of outdoor, family, and cultural experiences suited for all ages.
  • Welcoming Atmosphere: Benefit from a friendly community and a range of holiday accommodation options that ensure a comfortable stay.

Popular types of accommodation in Caledon

Caledon, Ontario, offers a delightful selection of holiday rentals including private homes, apartments, and condos, perfect for every traveller’s needs. Explore the stunning landscapes, including the picturesque Caledon Trailway and the charming Forks of the Credit Provincial Park, where outdoor adventures await. With friendly accommodations and a welcoming community, Caledon provides a relaxing getaway for those seeking transparency and savings in their holiday experience. Discover the ideal base for your Canadian adventure in this beautiful city.

  • Private Holiday Homes: Enjoy the charm and seclusion of a private residence, ideal for families or groups exploring Caledon.
  • Apartments: Experience the convenience of apartment living, offering a cosy and central base for your Caledon adventures.
  • Condos: Enjoy modern comforts and community facilities in a well-appointed condo setting during your stay.
  • Cabins: Relish the rustic appeal of a cabin retreat, perfect for a peaceful escape in Caledon’s scenic surroundings.
  • Villas: Indulge in the luxury and spaciousness of a villa, offering a refined experience for your holiday in Caledon.**

Top attractions in Caledon

Caledon in Ontario offers a variety of attractions from scenic reserve preserves and urban parks to a well-equipped convention centre, making it ideal for outdoor, family, and cultural experiences. Visitors can explore extensive trailways and enjoy local nightlife, ensuring a balanced mix of adventure and relaxation in this charming city.

  • Belfountain Conservation Area: Nestled in Caledon, this reserve offers a refreshing escape with scenic trails and tranquil natural beauty perfect for leisurely walks and picnics.
  • Alton Mill Arts Centre: Situated in Caledon, this arts centre exudes cultural vibes, showcasing local art and creative performances in a historic mill setting.
  • Glen Eagle Golf Club: Located in Caledon, this golf course country club provides a mix of adventure, relaxation and a family-friendly atmosphere, ideal for both casual and business enthusiasts.

Things to do recommended for couples

Seeking a romantic getaway in Caledon? Explore the stunning trails of the Caledon Trailway or enjoy a picnic at the picturesque Cheltenham Badlands. Don't miss a visit to the charming wineries for a delightful tasting experience, perfect for couples looking to unwind and connect.

Things to do recommended for families

Families visiting Caledon can explore scenic parks and engage in interactive local activities, making for a memorable family outing with plenty of kid-friendly adventures.

Things to do recommended for groups

Groups visiting Caledon can enjoy a guided hike through the breathtaking Caledon Hills, explore the picturesque Forks of the Credit Provincial Park, and indulge in local wines at nearby vineyards, providing a delightful taste of Ontario's natural beauty and charm.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're travelling in a group, as a family, with your pets or planning an extended stay, ensure you use the appropriate filters to prioritise your needs. Here are some Stayz booking tips to help you.

  • Traveling to Caledon with a group: Think about how many bedrooms you'll require, as well as additional features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily apply filters for all of these options and more on Stayz.
  • Traveling to Caledon with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, 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 some, a family holiday is never complete without their four-legged companion. If this resonates with you, then explore Stayz properties that welcome pets. Many pet-friendly accommodations offer feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Caledon: If you're searching for holiday rentals that offer special rates for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. You might also want to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around Caledon

Discover Caledon, Ontario, a delightful destination for outdoor adventure and family holidays. Enjoy the charm of Caledon East, the scenic beauty of Caledon Hills, and the inviting atmosphere of Cheltenham. Savour a delightful breakfast in Caledon while exploring its rich local culture and natural landscapes. This region perfectly blends a friendly, relaxed vibe with opportunities for luxury and adventure, making it an ideal retreat for every traveller.

  • Brampton: Brampton is a vibrant city located 14km from Caledon, offering an engaging mix of family, urban and business attractions. Travellers can explore a variety of shopping centres and an amusement park, while local landmarks include an expansive waterpark, a theme park, and a prominent sports facility stadium. This destination provides a dynamic blend of cultural experiences and modern city life, perfect for visitors seeking a blend of leisure and excitement.
  • Bolton: Bolton, a charming village in the Caledon area, invites visitors for a family-friendly, outdoor and urban experience. Here, you can enjoy leisurely rounds of golf, explore shopping centres, and experience the vibrant local community. The area boasts notable attractions such as a waterpark, a theme park, and a scenic park, making it an ideal choice for those who appreciate both natural beauty and a taste of urban flair.
  • Erin: Erin is a welcoming city situated 18km from Caledon, renowned for its outdoor, adventurous and eco-friendly atmosphere. Enthusiasts of natural landscapes can enjoy recreational areas, golf, and even skiing. The local attractions, including a park, a nature reserve, and a lake, offer plenty of opportunities to immerse oneself in the great outdoors and experience the serene beauty of the region.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January19.9°F (-6.7°C)Light RainMostly CloudyAverageSlightly Low
February20.5°F (-6.4°C)Light RainMostly CloudyAverageSlightly Low
March30.0°F (-1.1°C)Light RainMostly CloudyAverageAverage
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 Stayz is simple

Are you aiming to get the best value on your upcoming journey? Embracing flexible travel dates can often lead to lower prices, as rates typically fluctuate. Additionally, booking a longer stay might result in considerable savings. To discover a Stayz property that aligns with your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board offers a handy space to create fresh journeys, continue from where you last stopped, or review and arrange your plans. You will see the properties you have bookmarked or reserved neatly sorted under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/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)
  • Heart Lake Conservation Area (7.6 mi / 12.2 km)
  • Terra Cotta Conservation Area (9 mi / 14.4 km)
  • Island Lake Conservation Area (12.2 mi / 19.6 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 home 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. Stayz has holiday homes of all sizes, shapes and budgets, and we'll help you locate your ideal match.
How much does it cost to rent a holiday home in Caledon?
The average price for a holiday home 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 Stayz. Can't live without a private pool? Use our filters to select the features and amenities you need.
Are there pet-friendly holiday homes in Caledon?
Yes. You can pick from 12 holiday homes that cater to pets in Caledon. Lots of our pet-friendly holiday homes 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 Stayz.
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 Stayz, and then spend lazy days splashing about in a swimming pool that's just for you.
What are popular home amenities in Caledon?
When it comes to home amenities that guests look for in Caledon, a barbecue grill, a garden and ski-in/ski-out facilities are the most popular. With Stayz holiday homes, 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 homes in Caledon?
Take your pick of six Stayz 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 homes in Caledon that welcome kids?
Gather your entire family for an epic adventure in Caledon at one of our 12 family-friendly holiday homes. 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 homes in Caledon?
Yes, you can pick from three one-bedroom homes in Caledon. Whether you're looking for a townhouse or a fancy condo, Stayz'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 homes in Caledon?
Gather your besties and enjoy a relaxing escape in one of the two two-bedroom holiday homes Caledon has to offer.
Are there holiday homes with WiFi in Caledon?
You'll find seven holiday homes 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 Stayz.
How can I find holiday homes with air conditioning in Caledon?
Caledon has nine holiday homes where you can relax and recharge in air-conditioned comfort. To find a property on Stayz 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 home in Caledon?
The minimum required age is normally 16, 18 or 21. It can change from property to property on Stayz, so check the rules of your preferred Caledon stay before booking.
How long can I rent a holiday home 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 Stayz. 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.