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

Caledon Country Apt Near Golf, Venues & Horses - Caledon
9.7 55 reviews

Caledon Country Apt Near Golf, Venues & Horses

apartment, Caledon
This apartment is located on the Niagara Escarpment in Caledon, offering scenic views and easy access to the Bruce Trail, just a short drive from the charming town of Caledon Village. It has received excellent ratings for its location, cleanliness, and overall experience.
The self-catering accommodation is a spacious three-bedroom suite with one bathroom, suitable for up to six guests. Amenities include a well-equipped kitchen, a private entrance, a garden, a heated pool (for an extra fee), and a range of outdoor activities, including hiking, cycling, and bonfires.
3 Separate Sleeping Rooms On 23-acre Horse Farm - Caledon
10 53 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.
Beautiful Getaway In Orangeville - Caledon
9.9 58 reviews

Beautiful Getaway In Orangeville

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.
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.

Best Caledon vacation rentals with parking

Hockley Valley Resort - Caledon
8.1 1057 reviews

Hockley Valley Resort

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.
Mono Countryside Apartments - Caledon
No reviews

Mono Countryside Apartments

apartment, Orangeville
This Orangeville flat is located in Mono, 4 minutes by car from Hockley Valley Resort and 2 minutes by car from Sharon Lake, offering convenient access to local attractions such as Heathlands at Osprey Valley and Island Lake Conservation Area.
This one-bedroom, one-bathroom apartment accommodates two guests and includes a full kitchen, air conditioning, Wi-Fi, on-site parking, and a private terrace, with a garden and outdoor furniture also available.
Lavender Farm Century Cabin - Caledon
9.8 47 reviews

Lavender Farm Century Cabin

cabin, Adjala-Tosorontio
This charming cottage is located in the picturesque countryside of Adjala-Tosorontio, just a short drive from the Hockley Valley and its wineries. The property has received excellent reviews for its cleanliness, location, and overall experience.
The cottage has one bedroom and one bathroom, comfortably accommodating two guests. Guests can enjoy a fully equipped kitchen, a garden, and parking, along with modern amenities like running water and an indoor shower.
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.

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

The Hockley Hideaway, Sharing Our Unique Property For Your Unique Experiences️ - Caledon
10 52 reviews

The Hockley Hideaway, Sharing Our Unique Property For Your Unique Experiences️

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.
Walk To Downtown Orangeville With Free Parking & Games - Caledon
10 1 review

Walk To Downtown Orangeville With Free Parking & Games

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.
Charming Log Home - 25 Private Acres In Caledon - Caledon
10 3 reviews

Charming Log Home - 25 Private Acres In Caledon

apartment, Caledon East
This family-friendly apartment in Caledon East is located 45 kilometres from the Greater Toronto Area and close to the Albion Hills Conservation Area.
This 204 square metre holiday home offers 3 bedrooms and 2 bathrooms for up to 8 guests, featuring a kitchen with a fridge and microwave, a terrace, garden, spa, parking, and on-site walking trails.

Best Caledon vacation rentals with air conditioning

Bright, Modern, A Quiet Retreat On The Hill. - Caledon
No reviews

Bright, Modern, A Quiet Retreat On The Hill.

apartment, Caledon
This five-bedroom, four-bathroom flat offers a unique setting atop the Niagara Escarpment in Caledon, providing panoramic countryside views and peaceful rural surroundings with convenient access to urban centres, located just 5 kilometres from TPC and Alton, and 10 kilometres from Orangeville.
This spacious apartment accommodates up to 12 guests and boasts modern comforts, abundant natural light, a kitchen, air conditioning, a swimming pool, a fitness centre, and parking, all within easy reach of the Greater Toronto Area for day trips.
Mono Springs - Dream Country Escape W Pool/hot Tub - Caledon
9.8 50 reviews

Mono Springs - Dream Country Escape W Pool/hot Tub

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.
Escape To A World Of Comfort And Elegance. - Caledon
9.3 9 reviews

Escape To A World Of Comfort And Elegance.

apartment, Caledon East
This five-bedroom, three-bathroom property is a tranquil apartment located in a ravine with a private pond, offering a serene natural escape within Caledon East.
This spacious accommodation comfortably sleeps ten guests and features a gourmet kitchen, integrated sound system, and a luxurious steam shower, perfect for family reunions and group getaways.
Modern-detached 5 Bedroom100 Spotless-sleeps 13 - Caledon
No reviews

Modern-detached 5 Bedroom100 Spotless-sleeps 13

house, Caledon East
This detached 5-bedroom property in Caledon East is located approximately 34-40 kilometres from the Mississauga Convention Centre, Vaughan Mills, and Canada's Wonderland, with Toronto Pearson International Airport 27 kilometres distant.
This spacious dwelling offers accommodation for up to 13 guests across its 5 bedrooms, featuring a fully equipped kitchen with a dishwasher and oven, air conditioning, a fireplace, and complimentary WiFi, all within a 93 square metre floor area.
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