Compare Vacation Rentals & Airbnb in Caledon

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Caledon vacation rentals
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1633 Rentals and Airbnb in Caledon

Best family friendly Caledon vacation rentals

Among the 1633 accommodations in Caledon, here are the 4 best family friendly rentals

Luxurious 1000 Sq Ft Oasis - Caledon
9.0 84 reviews

Luxurious 1000 Sq Ft Oasis

apartment, Toronto
This luxurious Brampton apartment, situated 11km from Toronto Pearson International Airport and within easy driving distance of Canada's Wonderland and Casa Loma, offers convenient access to Mississauga and major attractions.
The 93 square metre property boasts a spacious one-bedroom layout sleeping up to six guests, complete with a fully equipped kitchen, in-unit laundry, free Wi-Fi, private parking, and a private entrance.
Serene Country Oasis  Optional Heated Pool - Caledon
9.6 14 reviews

Serene Country Oasis Optional Heated Pool

apartment, Caledon
This Caledon flat offers a peaceful country retreat in Cannon Gates, a rural setting providing seclusion yet remaining a short distance from cultural sites such as the Great War Flying Museum and Theatre Orangeville.
This family-friendly accommodation features three bedrooms, a fully equipped kitchen with a dishwasher, air conditioning, internet, and parking, with an optional private heated swimming pool available for an additional fee, and is ideal for outdoor pursuits including hiking and fishing within easy reach of attractions like the Caledon Ski Club.
Luxury 5 Star Stay In Brampton Ideal For Groups! - Caledon
No reviews

Luxury 5 Star Stay In Brampton Ideal For Groups!

house, Caledon East
This spacious holiday home in Caledon East is situated 19 kilometres from Toronto Pearson International Airport, 16 kilometres from the Mississauga Convention Centre, and 32 kilometres from Vaughan Mills Shopping Centre.
This family-friendly property offers 279 square metres of living space with 1 bedroom, 3 bathrooms, and accommodation for up to 15 guests, featuring a fully equipped kitchen, air conditioning, free WiFi, and a garden with a terrace.
3 Separate Sleeping Rooms On 23-acre Horse Farm - Caledon
10 59 reviews

3 Separate Sleeping Rooms On 23-acre Horse Farm

gîte, Adjala-Tosorontio
This Adjala-Tosorontio self-catering cottage is located 15 minutes (approx. 24km) east of Orangeville, 10 minutes (approx. 16km) from Palgrave, and 15 minutes (approx. 24km) from Hockley Valley Resort, offering easy access to skiing, golfing, and other activities.
This two-bedroom, one-bathroom holiday home sleeps four to six guests, features a full kitchen and laundry facilities, free Wi-Fi, and a private outdoor sitting area on a 23-acre horse farm.

Best Caledon vacation rentals with parking

Retreat In Hiker's Paradise With Outdoor Firepit - Caledon
9.5 53 reviews

Retreat In Hiker's Paradise With Outdoor Firepit

house, Georgetown
This self-contained basement apartment in Erin, Ontario, offers a peaceful countryside escape just a short drive (approx. 29km) from Georgetown and 72km from Toronto, with easy access to the Bruce Trail and other popular hiking routes.
The property comprises a one-bedroom, one-bathroom guest suite sleeping two, featuring a queen-sized bed, heated bathroom floors, a fully equipped kitchen with gas stove and toaster oven, Netflix, Wi-Fi, and two electric fireplaces; nearby Erin offers local shops and historic buildings within walking distance.
Fabulous Family Retreat, 1hr From To, Sleeps 8 - Caledon
10 1 review

Fabulous Family Retreat, 1hr From To, Sleeps 8

bungalow, Orangeville
This detached house is situated in Ontario's Headwaters region, just 10 kilometres from Hockley Valley Ski Resort and a short walk to Island Lake Conservation.
This family-friendly property offers accommodation for 8 guests with 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, hot tub, garden, and a home gym, with direct access to outdoor activities such as snowshoeing and trail walks.
Newly Built Bolton Studio - Caledon
9.8 56 reviews

Newly Built Bolton Studio

apartment, Bolton
This studio apartment is located in Bolton, a charming town just 40 kilometres from Toronto Airport and 72 kilometres from Downtown Toronto, offering a peaceful escape from the city. The accommodation has received excellent ratings for its cleanliness, location, and overall experience.
The self-contained studio is ideal for a small family or group of friends, comfortably accommodating up to four guests. Amenities include free Wi-Fi, a 55-inch TV with streaming services, a fully equipped kitchen with a fridge and microwave, a private entrance, free parking, and complimentary laundry facilities.
The Cozy-inn & Out - Caledon
9.8 24 reviews

The Cozy-inn & Out

apartment, Orangeville
This upper-level flat on Second Avenue in Orangeville offers a 2-bedroom, 1-bathroom dwelling for up to 4 guests, within 500 meters of Orangeville's shops, restaurants, Theatre Orangeville, and local parks, with easy access to Highway 10.
The apartment features a full kitchen, bright interiors, comfortable bedrooms, and a recently updated bathroom, making it ideal for self-catering and exploring nearby amenities.

Frequently Asked Questions about vacation rentals in Caledon

  • What should a first-time visitor not miss in Caledon?

    For a first-time visit, you definitely want to check out the Cheltenham Badlands. It's a unique geological formation with red, eroded clay cliffs, and it's a great spot for photography. You should also visit the Caledon Trailway, a 42-kilometre paved trail perfect for walking, cycling, or rollerblading.
  • What are the best Airbnb and vacation rentals in Caledon?

  • Which neighborhood in Caledon should you consider for a vacation rental?

    If you're looking for a vacation rental, the area around the Caledon Village is a good choice. It's a charming historic village with lots of shops, restaurants, and pubs, and it's close to the Caledon Trailway and other attractions. You could also consider the Alton area, which is known for its rolling hills and scenic farmland.
  • What are the most popular Airbnbs in Caledon?

  • What are the top family-friendly attractions in Caledon?

    Caledon has plenty to keep the kids entertained. The Albion Hills Conservation Area has great hiking trails, a playground, and a splash pad. The Belfountain Conservation Area is another great option with a scenic waterfall and a lovely walking trail. And for a bit of history, the Inglewood Windmill is a charming, working windmill that offers tours and demonstrations.
  • What are the best vacation 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 find fewer crowds and better deals on rentals, and the weather is still pleasant for outdoor activities.
  • What are the best rentals for families and kids in Caledon?

  • What events or festivals should visitors check out in and around Caledon?

    Caledon hosts a variety of events throughout the year. The Caledon Village Farmers' Market is a great place to find local produce and crafts, and it runs from June to October. The Caledon Fair is a popular annual event with agricultural displays, live music, and carnival rides, held in August. The Caledon Celtic Festival, held in September, celebrates Celtic culture with music, dance, and food.
  • What are the best rentals or Airbnbs with a jacuzzi in Caledon?

  • What are the best budget-friendly activities in Caledon?

    Caledon offers plenty of budget-friendly activities. You can explore the many hiking trails in the area, like the ones at the Albion Hills or Belfountain Conservation Areas. The Caledon Trailway is also a great option for walking, cycling, or rollerblading, and it's free to use. And don't forget to check out the Caledon Public Library, which has free events and programs throughout the year.
  • What are the best restaurants with local dishes in Caledon?

    For a taste of local cuisine, head to the Caledon Village. The 'The Caledon Hills' restaurant offers classic Canadian dishes with a modern twist. 'The Old Mill' is another good choice, with a menu featuring seasonal ingredients and a cozy atmosphere. If you're looking for something more casual, 'The Caledon Village Pub' offers a wide selection of pub food and local craft beers.
  • What are the best walking or cycling routes in Caledon?

    The Caledon Trailway is a must-do for cycling or walking. It's a 42-kilometre paved trail that runs through scenic countryside, and it's great for all levels of fitness. For a more challenging hike, try the Bruce Trail, which passes through Caledon and offers stunning views of the Niagara Escarpment.
  • Are there pet-friendly attractions in Caledon?

    Yes, many attractions in Caledon are pet-friendly. The Caledon Trailway welcomes leashed dogs, and many of the conservation areas, like the Albion Hills and Belfountain, also allow dogs on leash. Just be sure to check the specific regulations for each location.
  • What are the benefits of choosing a vacation rental in Caledon?

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities like kitchens and laundry facilities, which can be especially helpful for families or groups. You'll also have the flexibility to cook your own meals and enjoy the comforts of home.
  • What are the top sports attractions and facilities in Caledon?

    Caledon has a range of sports facilities, including the Caledon Community Complex, which has an indoor pool, fitness centre, and ice rink. The Caledon Trailway is also a great place for cycling, running, and walking. For golf enthusiasts, there are several golf courses in the area, including the Caledon Woods Golf Club and the Brampton Golf Club.

Popular destinations

Best Caledon vacation rentals with a balcony

⭐ Premium 5⭐ Luxury Stay Near Brampton - Caledon
No reviews

⭐ Premium 5⭐ Luxury Stay Near Brampton

apartment, Toronto
This 3-bedroom flat is located in Caledon, Ontario, offering easy access to Heart Lake Conservation Area, Terra Cotta Conservation Area, Brampton Fair Grounds, and Donald M. Gordon Chinguacousy Park.
This spacious accommodation comfortably sleeps six guests and features three bedrooms, two bathrooms, a terrace, garden, and parking, with air conditioning and internet provided for your convenience.
Clean Retreat Suite - Sleeps 4 (Queen Bed+futon) Near Brampton Innovation Go Stn - Caledon
10 2 reviews

Clean Retreat Suite - Sleeps 4 (Queen Bed+futon) Near Brampton Innovation Go Stn

apartment, Toronto
This newly renovated one-bedroom flat is located in Brampton West, offering direct GO train access to Downtown Toronto from Brampton Innovation District GO Station, and is situated 24.1 kilometres from Toronto.
This private suite accommodates up to four guests and features air conditioning, high-speed Wi-Fi, a dedicated workspace, and an outdoor barbeque facility, with Bramelia City Centre and Professor's Lake Recreation Area within easy reach.
Executive 5br-4bath Detached Bramp/miss Border - Caledon
9.9 14 reviews

Executive 5br-4bath Detached Bramp/miss Border

house, Toronto
This executive property is situated on the Brampton/Mississauga border, approximately 11 kilometres from the Mississauga Convention Centre and within a 32-48 kilometre radius of major Toronto attractions including Canada's Wonderland, York University, and Toronto city centre.
The 316 square metre house features a spacious five-bedroom, four-bathroom layout, accommodating up to 23 guests, and includes a fully equipped kitchen, private parking, complimentary Wi-Fi, and a flat-screen TV.
Cozy 3br Brampton Home Near Toronto And Mount Pleasant Go - Caledon
8.0 1 review

Cozy 3br Brampton Home Near Toronto And Mount Pleasant Go

house, Toronto
This Brampton holiday home is located 14.96 kilometres from Toronto Pearson International Airport and offers convenient access to Mount Pleasant GO for public transport.
The spacious accommodation spans 186 square metres, featuring one bedroom, three bathrooms, a fully equipped kitchen, air conditioning, a hot tub, a terrace, a garden, and private on-site parking, suitable for up to 15 guests.

Best Caledon vacation rentals with air conditioning

Charming Home Near Caledon Trails - Caledon
10 1 review

Charming Home Near Caledon Trails

apartment, Caledon East
This three-bedroom, two-bathroom flat in Caledon East offers exclusive use of the main level and a large garden, situated near the Caledon Trailway, equestrian centres, local shops, golf courses, and the Royal Ambassador Event Centre.
This accommodation, suitable for up to six guests, features a kitchen, air conditioning, parking, and internet, with laundry service available upon request, and provides direct access to the Caledon Trailway for outdoor pursuits.
Studio Apartment - Caledon
9.7 260 reviews

Studio Apartment

studio, 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.
Luxury Home For Families & Groups|sleeps 8 To 10 - Caledon
9.8 12 reviews

Luxury Home For Families & Groups|sleeps 8 To 10

apartment, Caledon East
This detached house in Caledon East offers four bedrooms and three and a half bathrooms, situated in a quiet, upscale neighbourhood with convenient access to shops, dining, parks, and major routes, approximately 4.5 kilometres from the historic Black Creek Pioneer Village.
The property features air conditioning, a garden, and parking, with a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, and accommodates up to eight guests.
The Bee Hive - Lower Level Raised Bungalow - Caledon
9.8 77 reviews

The Bee Hive - Lower Level Raised Bungalow

apartment, Orangeville
This self-contained lower apartment in Orangeville is situated at the lower level of a split-level bungalow adjacent to a garage, the precise address withheld but within easy reach of Orangeville's town centre (distance unspecified).
The one-bedroom flat offers a queen-sized bed, a fully equipped kitchen including a dishwasher and 50" LG Smart TV, and can comfortably accommodate two guests; parking is also available.
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