Caledon holiday rentals

We found 688 holiday rentals — enter your dates for availability
Discover a selection of 49 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:18 Dec - 25 Dec

Private kitchen
Interior
Exterior
Interior
Exceptional
(7 reviews)

A Castle on 3 Acres & 17,000 sq. ft. in Brampton, ON

Brampton

8% off
AU$16,167
for 7 nights, 1 room
AU$2,310 per night
includes taxes & fees
A Castle on 3 Acres & 17,000 sq. ft. in Brampton, ON
Living area
Living area
Living area
Interior
Exceptional
(16 reviews)

Alton Riverside Cottage Main Floor

Caledon

8% off
AU$3,132
for 7 nights, 1 cabin
AU$447 per night
includes taxes & fees
Alton Riverside Cottage Main Floor
Exterior
Living area
Private kitchen
Private kitchen
Exceptional
(11 reviews)

Private, Cozy Country Retreat in a cul-de-sac beside a 1,000-acre nature reserve

Mono

8% off
AU$3,220
for 7 nights, 1 home
AU$460 per night
includes taxes & fees
Private, Cozy Country Retreat in a cul-de-sac beside a 1,000-acre nature reserve
Property grounds
Property grounds
Interior
Interior
Exceptional
(7 reviews)

Forest Cabin

Erin

8% off
AU$1,025
for 7 nights, 1 cabin
AU$146 per night
includes taxes & fees
Forest Cabin
Dining
Property grounds
Private kitchen
Exterior
Excellent
(8 reviews)

Lakeview private suite with kitchen (Twin or King)

Adjala-Tosorontio

8% off
AU$1,028
for 7 nights, 1 villa
AU$147 per night
includes taxes & fees
Lakeview private suite with kitchen (Twin or King)
Magical Hockley Cabin
Heated pool with waterfall feature
Fireside Greatroom
Terrace/patio
Exceptional
(55 reviews)

“The Hockley Hideaway”, sharing our unique property for your unique experiences❤️

Mono

16% off
AU$8,869
for 7 nights, 1 home
AU$1,267 per night
includes taxes & fees
“The Hockley Hideaway”, sharing our unique property for your unique experiences❤️
Dining
Property grounds
Interior
Room
Excellent
(13 reviews)

Zen Nest - Cozy, conveniently located, and just minutes to the airport!

Brampton

8% off
AU$1,255
for 7 nights, 1 apartment
AU$179 per night
includes taxes & fees
Zen Nest - Cozy, conveniently located, and just minutes to the airport!
Dining
Living area
Terrace/patio
 Bedrooms  with office desk , chair and TV
Very good
(50 reviews)

Affordable Quiet 3 Bdrms + 2.5 bath Home in Toronto Area

Brampton

8% off
AU$1,436
for 7 nights, 1 home
AU$205 per night
includes taxes & fees
Affordable Quiet 3 Bdrms + 2.5 bath Home in Toronto Area
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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)
  • Hockley Valley Resort (12.9 mi / 20.8 km)
  • Wet 'n' Wild Toronto (13.3 mi / 21.4 km)
  • National Golf Club of Canada (14.9 mi / 24.1 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 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Caledon holiday homes prices shown on Stayz?
Stayz 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.
Are there any Caledon holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Caledon holiday homes?
You can find great discounts on holiday homes in Caledon on Stayz, 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.
Can I change or cancel my Caledon holiday home booking on Stayz?
To find Caledon holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Caledon?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Caledon holiday home?
Book your Caledon holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Caledon?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Caledon to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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