Spacious 4br Home Near Wedding Venues|free Parking
1 4
apartment , Caledon East
This Caledon East self-catering property is located in a peaceful residential area, a short drive from Caledon's attractions. The four-bedroom, two-bathroom house sleeps six guests and boasts a fully equipped kitchen (freezer, microwave, dishwasher), air conditioning, parking, Wi-Fi, and a private entrance.
Caledon
02/07 – 02/08
2112 €/nighttotal: 65472 € (31 )
Luxury, 4-bed House - Near Osprey Gc For Cdn Open
1 3
apartment , Caledon
This Caledon property, situated in a peaceful neighbourhood, offers easy access to local attractions within a short driving distance, its precise location requiring further specification for accurate distance calculations to landmarks. This 2700 sq ft (approximately 250 sq m) luxury dwelling boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a golf practice area, hot tub, and a basement recreation area with fitness equipment.
10 6 reviews
Caledon
07/07 – 08/07
208 €/nightfor 1 night
Walkout Basement With Private Entrance
2 2
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 95 reviews
Caledon
22/07 – 26/07
179 €/nighttotal: 716 € (4 )
Walk To Downtown Or Conservation Area, 2 Bedroom Home . Sleeps 4. Pets Welcomed
2 4
apartment , Orangeville
This apartment is situated in Orangeville, just a short walk from the town centre, offering easy access to shops, restaurants, and entertainment. It has received excellent ratings for location, cleanliness, and overall user experience. The 139 square metre property comfortably sleeps four guests in two bedrooms and one bathroom. The apartment features a fully equipped kitchen, a private patio, a luxurious bathroom with a clawfoot bathtub, and access to a garden, spa, and parking.
10 166 reviews
Caledon
22/07 – 26/07
163 €/nighttotal: 652 € (4 )
Hockley Haven
1 4
apartment , Orangeville
This charming self-catering apartment is situated in a peaceful country setting on a five-acre property just a short walk from the Pollinator Garden & Island Lake Trails and a six-minute drive from Hockley Valley Resort and Adamo Estate Winery. The apartment has received excellent ratings for location, cleanliness and user experience. The apartment is a newly renovated carriage house loft offering approximately 650 square feet of space, including a pull-out couch that can accommodate up to four guests. The apartment comes equipped with a fully fitted kitchen, a comfortable living area, a private garden and parking, as well as air conditioning and Wi-Fi.
10 1 review
Caledon
02/10 – 03/10
226 €/nightfor 1 night
Bright Garden Suite Near Orangeville & Alton
1 2
apartment , Caledon
This one-bedroom garden flat offers a peaceful retreat in Caledon, situated 7 kilometres from Orangeville's amenities and 3 kilometres from the Osprey Valley TPC golf course, with close proximity to the village of Alton. This self-catering accommodation sleeps up to four guests, featuring a full kitchen, in-suite laundry, air conditioning, parking, and a comfortable sofa bed for flexible sleeping arrangements.
9.8 12 reviews
Caledon
07/07 – 08/07
116 €/nightfor 1 night
Churchill Pines Guest House
1 2
house , Hillsburgh
Churchill Pines Guesthouse, a private two-storey apartment in northwest Caledon, is situated 16 kilometres from the Caledon Ski Club and 120 kilometres from Blue Mountain, providing a tranquil countryside escape. This guesthouse offers accommodation for up to three guests with one bedroom and one bathroom, featuring a full kitchen, a dedicated yoga/reading room, and a private deck, with proximity to equestrian venues and golf courses.
9.8 224 reviews
Caledon
02/10 – 03/10
64 €/nightfor 1 night
Studio Apartment
1 2
apartment , Caledon East
This Caledon East studio apartment offers excellent location, within easy walking distance of local shops, cafes, and parks. The self-contained unit sleeps two guests and features two bathrooms, air conditioning, parking, and internet access; nearby attractions and community events provide ample opportunities for exploration.
9.6 16 reviews
Caledon
07/07 – 08/07
140 €/nightfor 1 night
Brick House On Broadway - Coach House
1 2
house , Orangeville
This restored historic coach house, once part of Lester B. Pearson's grandparents' property, offers a private retreat in Orangeville, a short 500-meter walk from the town's historic core with its shops and restaurants, and is conveniently located for access to Hockley Valley, Mono Cliffs, and Island Lake hiking trails. This one-bedroom, one-bathroom dwelling accommodates two guests and features a fully equipped kitchen with a fridge, freezer, and microwave, air conditioning, internet, and parking, with an outdoor side yard complete with a picnic table for enjoying the mature tree surroundings.
Caledon
22/07 – 26/07
106 €/nighttotal: 424 € (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.
9.5 35 reviews
Caledon
07/07 – 08/07
391 €/nightfor 1 night
8 Acre Retreat | 8 Min Fr Tpc | Golf Hike Hot Tub
1 2
apartment , Caledon
This Caledon cottage, situated on an 8-acre site approximately 65km from Toronto and 10 minutes from the TPC Toronto at Osprey Valley golf course, offers a peaceful retreat. This three-bedroom, two-bathroom holiday home sleeps six guests and boasts a full kitchen, hot tub, fireplace, and fast Wi-Fi, alongside access to a fitness centre and parking.
9.7 163 reviews
Caledon
07/07 – 08/07
123 €/nightfor 1 night
R3 Suites In The Heart Of Alton. Frontunit
1 2
apartment , Caledon
This one-bedroom apartment is located in the charming hamlet of Alton, just a short walk from the historic Alton Mill and scenic trails. It has consistently received excellent ratings for location, cleanliness, and overall user experience. The apartment comfortably accommodates up to four guests and features a queen-sized bed, a pull-out sofa, and a small kitchenette. Guests can enjoy a private entrance, a quiet location, a garden, parking, internet access, air conditioning, and welcome treats.
Best family friendly Caledon holiday rentals
Among the 1212 accommodations in Caledon, here are the 4 best family friendly rentals
8.0 3 reviews
Caledon
22/07 – 26/07
719 €/nighttotal: 2876 € (4 )
Modern Retreat With Loft & Spa-like Jacuzzi Tub
4 4
apartment , Caledon East
This modern flat is situated in Brampton, providing convenient access to SilverCity Brampton Cinemas and Bowlero Brampton, both within 5 kilometres, as well as Heart Lake Conservation Area and Claireville Conservation Area. This spacious 260 square metre residence accommodates up to six guests across four bedrooms and three bathrooms, featuring a kitchen with essential appliances, air conditioning, a terrace, garden, parking, and a spa-inspired jacuzzi tub for relaxation.
9.0 25 reviews
Caledon
22/07 – 26/07
126 €/nighttotal: 504 € (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.
Caledon
22/07 – 26/07
445 €/nighttotal: 1780 € (4 )
Luxury, Home Away From Home.
4 4
apartment , Toronto
This luxurious Toronto apartment, situated on the Brampton/Caledon border, offers easy access to attractions such as Bovaird House and Devereaux House, and is approximately 0.6 kilometres from Eldorado Park. The 186 square metre property features a spacious four-bedroom, three-bathroom layout sleeping eight guests, complete with a fully equipped kitchen, air conditioning, parking, and a spa; nearby outdoor activities include fishing and walks in conservation areas.
8.6 4 reviews
Caledon
22/07 – 26/07
399 €/nighttotal: 1596 € (4 )
Cozy And Private Basement Apartment / Ideal For Relaxation Or Work
2 4
apartment , Toronto
This Brampton apartment, a 16km drive from Toronto and a 24km drive from Toronto Pearson International Airport, provides easy access to Canada's Wonderland and Woodbine Racetrack. The two-bedroom, one-bathroom property sleeps six guests and features a well-equipped kitchen, high-speed Wi-Fi, air conditioning, and pet-friendly accommodation.
Best Caledon holiday rentals with parking
10 1 review
Caledon
21/06 – 28/06
1000 €/nighttotal: 7000 € (7 )
Perfect 10 Acres Private Quiet Property For Small Events & Family Gatherings
4 6
cottage , Caledon
Vintage Cottage Retreat, a 4-bedroom property sleeping 14, is situated in Caledon, Ontario, approximately 72km from Yorkdale Shopping Centre and conveniently located near Forks of the Credit Provincial Park and the Bruce Trail. This 3,700 sq ft holiday home boasts a full kitchen with microwave and dishwasher, 4 bathrooms, a solarium, terrace, garden, parking, air conditioning, and a wood-burning fireplace; it also offers 10 acres of land ideal for camping, stargazing, and small events.
Caledon
22/07 – 26/07
125 €/nighttotal: 500 € (4 )
Modern 2 Bedroom Suite Near Airport Free Parking
1 4
house , Toronto
This 1-bedroom apartment in Brampton is situated 8 kilometres from Toronto Pearson International Airport, offering convenient access to attractions such as Canada's Wonderland (21 kilometres) and the Mississauga Convention Centre (16 kilometres). This 102 square metre suite accommodates up to 9 guests and features a fully equipped kitchen, air conditioning, complimentary Wi-Fi, and private parking, with in-suite laundry facilities and a dressing room for added comfort.
10 1 review
Caledon
07/07 – 08/07
218 €/nightfor 1 night
The Grassy Oasis - Garden Suite | King Bed | Detached | Self Contained
1 2
house , Toronto
This Brampton villa, located less than 1.6km from Brampton Memorial Arena and other central attractions like Gage Park and Brampton City Hall, offers convenient access to Brampton Station (a 23-minute walk). The 37-square-metre property features one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, patio, garden, parking, and in-unit laundry.
This spacious three-bedroom basement flat in Caledon, Ontario, offers easy access to Highway 410 and is a short drive from Brampton's restaurants and the Brampton Fair Grounds. The 88-square-metre (947-square-foot) property sleeps six, boasts a private basketball court, and includes amenities such as a fully equipped kitchen, Wi-Fi, Roku TV with streaming services, and a garden.
Frequently asked questions about holiday rentals 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 and September to October. You'll avoid the crowds and enjoy pleasant weather, perfect for exploring the outdoors.
What are the best Airbnb and holiday rentals in Caledon?
What events or festivals should visitors check out in and around Caledon?
The Caledon Fair in August is a popular event with live music, entertainment, and agricultural displays. For a unique experience, visit the Belfountain Pumpkinfest in October, featuring pumpkin carving, live music, and a farmers market.
What are the best budget-friendly activities in Caledon?
For budget-friendly fun, explore the Caledon Trailway on foot or by bike, enjoy a picnic at the Belfountain Conservation Area, or visit the Caledon Museum & Archives for free admission on certain days.
What are the best holiday rentals with a pool in Caledon?
What are the best restaurants with local dishes in Caledon?
For a taste of local cuisine, try The Belfountain Inn for traditional pub fare with a modern twist. The Old Mill Restaurant is another great option, offering classic Canadian dishes with a focus on fresh, seasonal ingredients.
What are the best rentals for families and kids in Caledon?
What are the best walking or cycling routes in Caledon?
The Caledon Trailway is a fantastic paved path stretching for 30km, perfect for walking or cycling. For a more challenging route, explore the trails in the Belfountain Conservation Area or the Albion Hills Conservation Area.
What are the best rentals or Airbnbs with a jacuzzi in Caledon?
Yes! Many attractions in Caledon are pet-friendly. The Caledon Trailway welcomes dogs on leash, and the Belfountain Conservation Area has designated dog-friendly areas. The Caledon Animal Shelter also welcomes dog visitors.
Destinations nearby
Best Caledon holiday rentals with a balcony
9.6 5 reviews
Caledon
22/07 – 26/07
327 €/nighttotal: 1308 € (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.
Caledon
22/07 – 26/07
348 €/nighttotal: 1392 € (4 )
Golf & Spa Retreat W/ Jacuzzi Near Tpc Toronto
3 4
apartment , Caledon
This detached house in Alton, Caledon, is situated in a peaceful rural area offering countryside views and easy access to Highway 10, placing it a short drive from Orangeville's amenities and within proximity of Forks of the Credit Provincial Park, Belfountain Conservation Area, Cheltenham Badlands, and Island Lake Conservation Area. Spanning 223 square meters, this residence accommodates up to six guests with three bedrooms, two bathrooms, two living rooms, a fully equipped kitchen, and outdoor amenities including a deck, gazebo, jacuzzi, and fire pit, alongside private parking for 8-10 vehicles.
8.0 9 reviews
Caledon
22/07 – 26/07
94 €/nighttotal: 376 € (4 )
Suite A 2 Bedroom Apartment
2 4
apartment , Toronto
This Brampton apartment, situated approximately 16 kilometres from Toronto Pearson International Airport and 21 kilometres from Canada's Wonderland and Vaughan Mills Shopping Centre, offers convenient access to major attractions. Sleeping up to seven guests, this self-catering flat boasts a fully equipped kitchen, private parking, a terrace, and an outdoor fireplace, plus nearby amenities including a coffee shop and mini-market.
Caledon
02/10 – 03/10
426 €/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
Caledon
21/06 – 28/06
236 €/nighttotal: 1652 € (7 )
Home In Brampton
1 6
apartment , Toronto
This Toronto flat offers convenient access to HWY 410 and Mayfield Road, situated near a Walmart and a public transport bus stop. This spacious accommodation sleeps up to eight guests across four bedrooms, featuring a private backyard, in-unit laundry, and parking for three vehicles, with a kitchen equipped with a fridge and dishwasher.
9.6 4 reviews
Caledon
22/07 – 26/07
115 €/nighttotal: 460 € (4 )
Charming Private 2 Bedroom 1 Bathroom Basement Suite In Awesome Brampton
2 4
apartment , Toronto
This Brampton apartment, near Vaughan Mills and Square One shopping centres, offers convenient access to Canada's Wonderland and Donald M. Gordon Chinguacousy Park, all within a reasonable driving distance. This 63 square metre (678 square feet) two-bedroom, one-bathroom flat sleeps four guests and includes a fully equipped kitchen with fridge, microwave, dishwasher, WiFi, air conditioning, a terrace, garden, parking, and a washing machine.
9.7 6 reviews
Caledon
02/07 – 02/08
891 €/nighttotal: 27621 € (31 )
10 Acres Private Bruce Trail Cottage For 14 Guests
1 3
apartment , Caledon
This Caledon cottage, located on a 10-acre property bordering the Bruce Trail and approximately 72 kilometres from Yorkdale Shopping Centre, offers creek access. The 3,700 sq ft property sleeps up to 14 guests in four bedrooms and three bathrooms, boasting a solarium, fully equipped kitchen, ample parking, and king-sized beds; nearby activities include hiking the Bruce Trail and exploring the Niagara Escarpment.
9.8 13 reviews
Caledon
07/07 – 08/07
187 €/nightfor 1 night
Stunning & Spacious 1 Bedroom Oasis
1 2
apartment , Toronto
This Brampton apartment, situated approximately 5 kilometres from Donald M. Gordon Chinguacousy Park, Historic Bovaird House, and Bowlero Brampton, offers easy access to local attractions. The one-bedroom, one-bathroom flat sleeps four guests and features a fully equipped kitchen, in-unit laundry, free Wi-Fi, air conditioning, and access to an on-site water park, swimming pool and spa.