This spacious bungalow is situated on nine private acres in New Tecumseth, Ontario, a two-minute drive (approximately 1.6 kilometres) from local shops and a Tim Hortons. The 4-bedroom, 3.5-bathroom property boasts a large open-plan kitchen, dining, and living area, a gym, three TVs, a treehouse with additional sleeping, ample outdoor space including fire pits and a dog run, and accommodates up to ten adults.
9.8 48 reviews
Caledon
25/08 – 27/08
£585/nighttotal: £1170 (2 )
Mono Springs - Dream Country Escape W Pool/hot Tub
1 2
apartment , Orangeville
This four-bedroom apartment is located in Mono, a rural area just 15 kilometres from Orangeville town centre, offering a peaceful escape from the hustle and bustle. The apartment enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment features a spacious and well-equipped kitchen, perfect for self-catering, and can comfortably accommodate up to eight guests. Enjoy a range of amenities including a private hot tub, a heated swimming pool (seasonal), a large bonfire pit, and 10 acres of land with trails for exploring the surrounding countryside.
9.7 29 reviews
Caledon
22/07 – 26/07
£317/nighttotal: £1268 (4 )
Relaxing 4br Family Stay | Cozy & Spotless Retreat
1 4
apartment , Caledon East
This four-bedroom, three-bathroom detached house is situated in Brampton, approximately 20 kilometres from Caledon East, offering easy access to major highways. The self-catering property boasts a modern open-plan layout, sleeping up to six guests, and includes a fully equipped kitchen, high-speed internet, in-unit laundry facilities, and a garden; complimentary breakfast is provided for stays of seven nights or more (up to £40 value, ordered via Instacart).
10 46 reviews
Caledon
25/08 – 27/08
£902/nighttotal: £1804 (2 )
The Hockley Hideaway, Sharing Our Unique Property For Your Unique Experiences️
5 2
apartment , Orangeville
This holiday home is situated in Mono, just 8km from Hockley Valley Resort and 14km from Island Lake Conservation Area, offering a peaceful retreat in a scenic setting. The property has received excellent user ratings, suggesting a high standard of comfort and service. This spacious property provides accommodation for up to 10 guests in its 5 bedrooms. The house boasts a range of modern amenities, including a private pool, a jacuzzi, a tennis court, and a fully equipped kitchen, making it ideal for families or groups looking for a relaxing and enjoyable stay.
10 68 reviews
Caledon
25/08 – 27/08
£354/nighttotal: £708 (2 )
Charming Log Home - 25 Private Acres In Caledon
1 2
apartment , Caledon East
This apartment is located in Caledon East, a tranquil area on the rolling hills, just 45 minutes from the Greater Toronto Area (GTA). It has received excellent ratings for location, cleanliness, and user experience. This three-bedroom, two-bathroom home can accommodate up to eight guests. The apartment comes equipped with a modern kitchen, a wood-burning fireplace, two TVs, and a garden, offering a serene setting with nearby trails, a pond, and winter activities like skating and snowshoeing.
Caledon
22/07 – 26/07
£111/nighttotal: £444 (4 )
Cozy Caledon Getaway - Suite B
2 4
apartment , Caledon East
This Caledon East apartment is conveniently located in a quiet, family-friendly neighbourhood, offering easy access to attractions such as the Brampton Fairgrounds and Donald M. Gordon Chinguacousy Park (distances unspecified). The two-bedroom, one-bathroom flat sleeps four guests and features air conditioning, internet access, and a comfortable, stylish interior ideal for families or groups visiting Caledon East.
9.7 94 reviews
Caledon
02/10 – 03/10
£101/nightfor 1 night
Modern Private Suite | Full Kitchen, Self Check-in
1 2
apartment , Orangeville
This newly renovated Orangeville basement flat is situated near Orangeville Hospital, a two-minute walk away, with easy access (a five-minute drive, approximately 3.2km) to the town's hockey arenas and a short drive to the town centre. The 700 sq ft self-contained apartment sleeps four, features a full kitchen, free parking, and is ideal for hockey fans, hospital visitors, or those exploring Orangeville's shops and restaurants.
9.7 12 reviews
Caledon
25/08 – 27/08
£130/nighttotal: £260 (2 )
The Enchanted Cottage
1 2
cabin , Orangeville
This charming cottage is situated close to the centre of Orangeville, offering easy access to the town's amenities and attractions. The surrounding area is peaceful and green, with a lively stream flowing nearby. The cottage has one bathroom and can comfortably accommodate up to four guests. It is equipped with a kitchen, air conditioning, parking, and internet access, providing all the essentials for a relaxing stay.
Caledon
07/07 – 08/07
£104/nightfor 1 night
Cozy One-bedroom Walkout Apartment With Living Area & Full Kitchen- Entire Home
1 2
apartment , Bolton
This one-bedroom flat in Brampton offers convenient access to Mississauga and Toronto, situated within 500 meters of local parks and cultural sites such as Bovaird House and the Lester B. Pearson Memorial Theatre. This private walk-out suite accommodates two guests with a fully equipped kitchen, free Wi-Fi, a 50-inch TV, and a private porch and backyard, providing easy reach to Brampton Fair Grounds and Donald M. Gordon Chinguacousy Park.
Caledon
02/10 – 03/10
£116/nightfor 1 night
Cozy Basement Apartment (700 Sq Ft) With Full Kitchen
1 2
apartment , Orangeville
This newly renovated 700 sq ft basement flat is centrally located in Orangeville, offering convenient access with a 2-minute walk to the hospital and a 5-minute drive to the hockey arenas. This self-catering accommodation for two features a full kitchen, air conditioning, and complimentary driveway parking, with nearby attractions including Island Lake Conservation Area and Hockley Valley Provincial Park.
9.8 30 reviews
Caledon
22/07 – 26/07
£250/nighttotal: £1000 (4 )
#1 Best Deal In Brampton
1 4
apartment , Caledon East
This spacious Caledon East house, near Toronto, offers easy access to Highway 410 and Pearson International Airport, approximately 60km away. Sleeping up to nine guests, this four-bedroom, three-bathroom property boasts a modern kitchen, 4K microLED smart TV, private parking, and a fitness centre; professional cleaning ensures a comfortable stay.
9.6 34 reviews
Caledon
22/07 – 26/07
£308/nighttotal: £1232 (4 )
Stylish, Modern & Cozy Family Home
1 4
apartment , Caledon East
This Caledon East home, ideally located near local grocery stores and parks, offers convenient access to public transport via nearby bus routes. Sleeping up to eight comfortably in three bedrooms and two sofa beds, this three-bedroom property boasts two and a half bathrooms, a fully equipped kitchen, and a main floor workspace, perfect for families or groups visiting Caledon East.
Discover Family-Friendly Self-Catering Rentals in Caledon
Getting the holiday rental right makes all the difference for a family trip to Caledon. Find city attractions within easy reach. Start comparing now.
9.5 30 reviews
Caledon
07/07 – 08/07
£84/nightfor 1 night
Lovely Cozy Apartment
1 2
apartment , Toronto
This Brampton apartment, situated 12km from Toronto Pearson International Airport and 19km from Canada's Wonderland, offers convenient access to major attractions. The 800 square metre property boasts one bedroom, one bathroom, sleeps three guests, and includes free Wi-Fi, private parking, a fully equipped kitchen, and a flat-screen TV with streaming services.
10 2 reviews
Caledon
22/07 – 26/07
£301/nighttotal: £1204 (4 )
The Cinema House: 98" Theater I Near Airport I Bbq I Luxury Home
3 4
apartment , Toronto
This Brampton family home, approximately 4.2km from Century Gardens Arena and within 2km of Donald M. Gordon Chinguacousy Park, offers easy access to Toronto attractions. Sleeping eight guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen, jacuzzi, terrace, garden, parking, and free Wi-Fi; nearby recreational activities include Victoria Park Arena.
9.6 5 reviews
Caledon
22/07 – 26/07
£282/nighttotal: £1128 (4 )
#1 Best Deal In Brampton
4 4
apartment , Caledon East
This Caledon East holiday home is situated within 10 kilometres of Brampton Fair Grounds, Camden Dog Park, Downey's Farm Market, and Historic Bovaird House. This spacious four-bedroom property, boasting 242 square metres of floor area, comfortably accommodates nine guests and features a fully equipped kitchen, private balcony, free Wi-Fi, and a fireplace.
9.9 57 reviews
Caledon
02/10 – 03/10
£170/nightfor 1 night
Beautiful Getaway In Orangeville
1 2
apartment , Orangeville
This apartment is situated in a peaceful neighbourhood just a short 800-metre walk from Island Lake Conservation Area, a popular spot for nature walks and outdoor activities, and a two-minute drive from Orangeville's town centre. The property boasts a spacious living area, a fully equipped kitchen, and a private deck with a barbecue, perfect for relaxing after a day exploring the surrounding area.
Compare Holiday Rentals with Parking in Caledon
Park up and enjoy the city centre. These holiday rentals in Caledon come with a free car park on-site. Start comparing now.
Caledon
22/07 – 26/07
£89/nighttotal: £356 (4 )
Bright & Cozy 2-bedroom Main Floor Suite
2 4
apartment , Toronto
This ground-floor flat offers private rental in Brampton, central to the 410 highway and a short drive from Toronto's attractions, with nearby points of interest including Devereaux House and Heart Lake Conservation Area. The 84 square metre accommodation accommodates up to six guests with two bedrooms, a fully equipped kitchen, a fireplace, and a television, plus a garden and dedicated parking.
8.3 22 reviews
Caledon
07/07 – 08/07
£169/nightfor 1 night
The Grassy Oasis
1 2
house , Toronto
The Grassy Oasis villa is located in Brampton, a suburb of Toronto, just 6.6 km from the Mississauga Convention Center and 27 km from the Aviva Centre. This peaceful retreat offers a quiet escape from the city, with easy access to Toronto's attractions. The villa is a one-bedroom property with one bathroom, covering 37 square meters and accommodating up to three guests. It features a fully equipped kitchen, a private garden, outdoor play equipment, free parking, and a private courtyard.
9.4 3 reviews
Caledon
07/07 – 08/07
£367/nightfor 1 night
Fall Nordic Cottage Retreat With Hot Tub 60 Minutes From City
2 2
apartment , Caledon
This two-bedroom flat is located on an 8-acre estate in Caledon, 129 kilometres from Toronto and 13 minutes from TOC Osprey, offering proximity to Theatre Orangeville and the Great War Flying Museum. This property provides accommodation for four guests, featuring two primary bedrooms with en-suite bathrooms, a kitchen with a microwave oven and dishwasher, air conditioning, a Jacuzzi, parking, and an outdoor patio, with nearby trails and arts centres like Alton Mill Arts Centre.
9.0 25 reviews
Caledon
22/07 – 26/07
£108/nighttotal: £432 (4 )
Tosam Luxury Lodge Two Bedroom Suite
2 4
apartment , Toronto
This two-bedroom flat is located in Brampton, a suburb just west of Toronto, 30 kilometres from Canada's Wonderland and 37 kilometres from Casa Loma. The apartment has received excellent user ratings and very good ratings for location and cleanliness. The 93 square metre flat comfortably sleeps four guests. It offers a range of amenities, including free Wi-Fi, private parking, a fully equipped kitchen, outdoor dining space, and air conditioning.
Frequently asked questions about holiday rentals in Caledon
What should a first-time visitor not miss in Caledon?
For a first-time visit to Caledon, you shouldn't miss the beautiful Cheltenham Badlands. These unique geological formations are a must-see, and you can also check out the Caledon Trailway, a scenic paved path perfect for cycling or a leisurely stroll.
What are the best Airbnb and holiday rentals in Caledon?
Which neighborhood in Caledon should you consider for a vacation rental?
If you're looking for a vacation rental in Caledon, the neighbourhood of Palgrave is a great option. It's close to the Caledon Trailway and has a good selection of restaurants and shops. You could also consider the more rural area of Inglewood, which is close to the Cheltenham Badlands and offers a more peaceful atmosphere.
What are the top family-friendly attractions in Caledon?
Caledon is full of family-friendly attractions. The Belfountain Conservation Area is a great spot for a picnic or a hike, and the Albion Hills Conservation Area has a playground and a splash pad. For something a little different, check out the Caledon Animal Shelter, where you can meet the animals and learn about adoption.
What are the best holiday rentals with a pool in Caledon?
When is the best time to book a vacation rental in Caledon?
The best time to book a vacation rental in Caledon is during the shoulder seasons, from April to May or September to October. You'll avoid the crowds and enjoy pleasant weather, perfect for exploring the outdoors.
What are the best rentals for families and kids in Caledon?
What are the best budget-friendly activities in Caledon?
Caledon has plenty of budget-friendly activities. You can enjoy a free walk along the Caledon Trailway, explore the Cheltenham Badlands, or have a picnic at one of the many parks. For a unique experience, visit the Caledon East Farmers' Market and browse the local produce and crafts.
What are the best rentals or Airbnbs with a jacuzzi in Caledon?
What are the best restaurants with local dishes in Caledon?
For a taste of local cuisine, check out The Millcroft Inn. They offer a classic Canadian menu with fresh, seasonal ingredients. If you're looking for something more casual, try the Caledon Hills Golf Club, which has a great restaurant with a view of the course.
What are the best walking or cycling routes in Caledon?
The Caledon Trailway is a great option for both walking and cycling. It's a 42 km paved path that runs through the heart of Caledon, offering scenic views of the countryside. For a shorter walk, try the Bruce Trail, which has several access points in Caledon.
Are there pet-friendly attractions in Caledon?
Yes, there are many pet-friendly attractions in Caledon. The Caledon Trailway is a great place to walk your dog, and many parks and conservation areas are dog-friendly. The Belfountain Conservation Area even has a designated off-leash dog area.
What are the benefits of choosing a vacation rental in Caledon?
Vacation rentals in Caledon offer more space and privacy than a hotel. They often have kitchens and laundry facilities, making them ideal for families or groups. You can also find rentals with unique features like fireplaces or hot tubs, adding to the overall experience.
What are the top sports attractions and facilities in Caledon?
Caledon is a great place for sports enthusiasts. The Caledon Hills Golf Club has a challenging 18-hole course, and there are several other golf courses in the area. For other activities, check out the Caledon Tennis Club or the Caledon Soccer Club.
Destinations nearby
Check Out Holiday Rentals with a Balcony in Caledon
Private balconies with city skyline views come as standard at these holiday rentals in Caledon for a lovely start to your day.
Caledon
22/07 – 26/07
£91/nighttotal: £364 (4 )
The Ecstatic Joy Of Heaven
1 4
apartment , Caledon East
This one-bedroom Brampton apartment, a short 1.4km drive from Caledon East, offers easy access to Mount Pleasant Station, The Old Pro Driving Range (1.3km), and Eldorado Park & Historic Bovaird House (9.7km). The self-catering flat sleeps four, includes a fully equipped kitchen with dishwasher, in-unit laundry, and a Smart TV, and is perfect for exploring Brampton's attractions and the surrounding Caledon East countryside.
8.1 1501 reviews
Caledon
07/07 – 08/07
£243/nightfor 1 night
Hockley Valley Resort
1 2
resort , Orangeville
Hockley Valley Resort in Orangeville offers a family-friendly escape, located under 15 minutes by car from Orangeville and the Hockley Valley Provincial Nature Reserve, with Luther Marsh Conservation area approximately 100 kilometres away. This establishment boasts an 8,000 sq ft spa, indoor and outdoor swimming pools, an 18-hole golf course, a ski hill with 16 runs, and on-site dining at the farm-to-table restaurant, Cabin, and the lobby bar, Babbo, with Adamo Estate Winery just 1 kilometre down the road.
Caledon
22/07 – 26/07
£581/nighttotal: £2324 (4 )
Luxury 4br Stay With Swim Spa, Golf And Fireplaces
4 4
house , Caledon East
This luxury four-bedroom property is situated in Inglewood, 26 kilometres from the Mississauga Convention Centre, with other attractions within a 31 to 45 kilometre radius. This spacious 465 square metre residence accommodates up to 15 guests and features a swim spa, hot tub, golf amenity, air conditioning, a garden, free WiFi, and a fitness centre, with a fully equipped kitchen and multiple fireplaces.
Caledon
02/10 – 03/10
£367/nightfor 1 night
Walk To Downtown Orangeville With Free Parking & Games
3 2
house , Orangeville
This Orangeville holiday home is a 7-minute walk from Theatre Orangeville and is located approximately 48 kilometres from Wild Water Kingdom. This property accommodates up to 11 guests with 3 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, Wi-Fi, an indoor play area, and a fireplace, with laundry services and free parking available.
Best Caledon holiday rentals with air conditioning
10 6 reviews
Caledon
22/07 – 26/07
£154/nighttotal: £616 (4 )
Walkout Basement With Private Entrance
2 4
apartment , Caledon East
This Caledon East apartment is situated 1.7 km from the Lake Conservation Area and within 10 km of attractions including the Brampton Fair Grounds and Chinguacousy Park. The two-bedroom, one-bathroom flat sleeps four guests and boasts a fireplace, full kitchen with dishwasher, in-building fitness centre, and parking, along with a Smart TV for entertainment.
10 33 reviews
Caledon
22/07 – 26/07
£135/nighttotal: £540 (4 )
Countryside Escape Pooltable Firepit Basketball
1 4
apartment , Guelph/Eramosa
The Ospringe Retreat is a family-friendly flat located in the Guelph/Eramosa district, situated 15 kilometres from Guelph, 32 kilometres from Milton, and 72 kilometres from Pearson Airport, offering a countryside escape within an exclusive estate community. This spacious main-level walkout basement unit accommodates up to four guests, featuring a fully equipped kitchen with a fridge, freezer, and microwave, air conditioning, a private patio with a fire pit, a media room with a projector, and indoor garage parking.
Caledon
07/07 – 08/07
£52/nightfor 1 night
Private Unit/ With Washroom And Laundary
1 2
apartment , Toronto
This flat is located in a well-connected Toronto district, providing easy access to popular attractions like the CN Tower, which is approximately 3.5 kilometres away. This property accommodates up to four guests and features a fully equipped kitchen, a dedicated dining area, a comfortable living room, air conditioning, and internet access, offering a home-away-from-home experience.
This Caledon East flat offers convenient access to local attractions, with the Royal Ambassador Banquet a 7-minute drive and Albion Hills Conservation Area a 10-minute drive away. This serviced apartment features a fully equipped kitchen, on-site parking, internet access, and an in-unit washer and dryer, providing a comfortable stay for those exploring the area.