Caledon holiday lettings

We found 730 holiday rentals — enter your dates for availability

Discover a selection of 55 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:4 Sept - 11 Sept

Image gallery for Forest Cabin

Living area
9.4 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Forest Cabin

Erin

8% off
Price is £552
for 7 nights, 1 cabin
£79 per night
includes taxes & fees
Forest Cabin

Find spaces that suit your style

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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)
  • Caledon Country Club (4.7 mi / 7.6 km)
  • Albion Hills Conservation Area (6.7 mi / 10.8 km)
  • Osprey Valley Golf (8.5 mi / 13.6 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 best area to stay in Caledon when booking a holiday rental?
When looking for the best area to stay in Caledon, Ontario, a delightful choice would be the neighbourhood surrounding the picturesque village of Caledon East. This area offers a charming blend of rural beauty and modern conveniences, making it an ideal spot for a holiday rental. Here, you can enjoy the scenic landscapes, with ample opportunities for outdoor activities such as hiking and cycling.

Caledon East also boasts attractions like the vibrant Caledon East Community Park, great for family picnics and leisurely strolls. Additionally, the nearby Caledon Trailway is a wonderful destination for those who enjoy walking or biking through nature. The area features a variety of properties, from quaint cottages to spacious homes, suiting different preferences and needs.

Another attractive option is the area around Bolton, which offers a lively option with easy access to shops and restaurants. Bolton is known for its welcoming community vibe and nearby attractions, including the beautiful Heart Lake Conservation Area, where visitors can enjoy various outdoor activities, including canoeing and fishing.
How much does it cost to rent a holiday home in Caledon?
Prices for holiday rentals in Caledon vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Caledon to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Caledon holiday house rentals?
You can find great discounts on house rentals in Caledon on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Caledon ski resort rentals?
For skiing near Caledon, the closest resort is the Caledon Ski Club, which offers a selection of rental options in the surrounding areas. Travellers looking for convenient accommodations should consider properties in nearby towns such as Bolton and Palgrave. In these areas, you can find comfortable chalets and modern condos that often include amenities like fully equipped kitchens, cozy living rooms with fireplaces, and ski storage facilities to make your stay enjoyable.

The Bolton area, with its proximity to the ski club, features various lodgings, including private homes and shared accommodations, suitable for families or groups. Many of these properties provide outdoor spaces for relaxation after a day on the slopes, such as patios or decks, and some may even offer hot tubs for unwinding.

Additionally, the scenic beauty of the surrounding countryside enhances the experience for those who enjoy winter activities beyond skiing, such as snowshoeing and cross-country skiing. Rentals in this region often come with easy access to local shops and dining options, making it convenient for travellers to enjoy both the slopes and the local charm.
What is the most popular type of holiday rental accomodation in Caledon?
In Caledon, holiday houses are the predominant type of holiday rental, with around 104 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups seeking comfort and convenience. Many holiday houses also come with outdoor spaces such as decks or gardens, superb for enjoying the scenic views of the surrounding countryside.

Apartments are another popular option, with about 40 units spread across various neighbourhoods. These typically offer a more compact living space, including kitchens and living areas, appealing to couples or solo travellers looking for a convenient base to explore the region. There are also around 12 cottages and 12 villas available, providing a more rustic or luxurious alternative, respectively. Cottages often feature charming, home-like amenities, while villas can offer upscale facilities and beautiful surroundings. Additionally, several cabins are available, providing a unique and cosy retreat for those wanting to immerse themselves in nature.
Are there any family house rentals in Caledon?
In Caledon, Ontario, families will find a variety of holiday rentals—there are 25 available throughout the area. This region is known for its picturesque landscapes, making it an excellent choice for family getaways. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can enjoy some fresh air.

Visitors can also expect amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for all. The locale is home to several parks and recreational areas, great for family outings, and offers opportunities for activities like hiking and cycling.
Can I rent a holiday home with a pool or hot tub in Caledon?
In Caledon, there are several holiday homes available for rent that feature pools and hot tubs, making it a delightful choice for travellers seeking relaxation and leisure. This picturesque region, known for its natural beauty and charming rural landscapes, offers a variety of properties in neighbourhoods such as Caledon East and the scenic areas surrounding the Credit River.

Rentals typically come with amenities such as private swimming pools, outdoor hot tubs, and spacious decks or patios ideal for entertaining and enjoying the serene surroundings. Many properties also include fully equipped kitchens, allowing guests to prepare meals while enjoying the comforts of a home away from home.
Can I find long-stay holiday rentals in Caledon?
A long-stay holiday rental in Caledon is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Caledon?
In Caledon, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. The area is known for its scenic landscapes and outdoor activities, making it an appealing choice for pet owners. Many of the holiday rentals come equipped with amenities such as spacious backyards, fully furnished kitchens, and comfortable living areas, allowing guests to relax and enjoy their stay.

Caledon offers access to various parks and nature reserves, great for walks and outdoor adventures with pets. For instance, the Caledon Trailway is a popular spot for hiking and biking, where visitors can enjoy the natural beauty of the region alongside their pets. Additionally, the nearby Forks of the Credit Provincial Park features picturesque trails and stunning views, making it an ideal destination for a day out with your four-legged friends.
Are there any remote work holiday rentals in Caledon?
In Caledon, Ontario, there is a substantial selection of remote work holiday rentals, with around 156 properties available to choose from. This charming region, known for its picturesque landscapes and outdoor activities, provides an excellent backdrop for working remotely. Many of the rentals offer dedicated workspaces, complete with desk chairs and free Wi-Fi, ensuring that guests can stay productive during their stay.

Accommodations often come equipped with essential amenities such as comfortable living areas, fully equipped kitchens, and sometimes even outdoor spaces for relaxation after a long day of work. The area's proximity to nature trails and conservation parks allows for refreshing breaks and outdoor activities, making it an appealing choice for those seeking both productivity and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Caledon holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Caledon with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Caledon?
In Caledon, popular rental amenities include kitchens, allowing guests to prepare their own meals, and onsite parking for added convenience. Many properties also feature coffee and tea makers, superb for enjoying a warm beverage after a day of exploring. Additionally, rentals often come with decks or patios, providing outdoor space to relax and take in the scenic surroundings. Fireplaces are also a common amenity, creating a cozy atmosphere during cooler evenings.
When is the best time to visit Caledon for a holiday rental?
The best time to visit Caledon for a holiday rental is during the warm summer months, particularly in July. This period marks the peak season, attracting visitors eager to enjoy outdoor activities amidst the natural beauty of this region. With temperatures typically ranging from 15 to 25 degrees Celsius, it's ideal for hiking, cycling, and exploring the picturesque landscapes that Caledon has to offer.

July is particularly vibrant, as local festivals and events come alive, providing a lively option that enhances your holiday experience. You can immerse yourself in the community spirit while enjoying various outdoor activities, from leisurely walks in the scenic parks to more adventurous pursuits. The lush greenery and blooming flowers create a stunning backdrop for your adventures.

For those looking for a more budget-friendly option, consider planning your visit in November. This month offers a quieter experience, superb for enjoying the serene beauty of Caledon's countryside and the stunning autumn colours without the hustle and bustle of peak tourist traffic.
How early should I book a Caledon holiday rental?
Book your Caledon holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Caledon?
In Caledon, visitors can explore a range of attractions that showcase the area's natural beauty and outdoor activities. The Caledon Trailway, a scenic multi-use trail, offers opportunities for walking, cycling, and horseback riding through picturesque landscapes. The popular Heart Lake Conservation Area features a beautiful lake, picnic areas, and trails, making it a great spot for family outings and nature enthusiasts.

For those interested in horticulture, the nearby Allan Gardens boasts a stunning conservatory filled with exotic plants and seasonal flower displays. The picturesque village of Caledon East offers charming shops and cafes, providing a quaint atmosphere for leisurely strolls. Additionally, the area is known for its wineries and local farms, where visitors can enjoy tastings and fresh produce.

The scenic Forks of the Credit Provincial Park is also a highlight, offering stunning views, hiking trails, and opportunities for photography, particularly in the autumn months when the foliage is vibrant.
Can I change or cancel my Caledon home rental booking on Vrbo?
To find Caledon holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Caledon holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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