Compare Vacation Rentals & Airbnb in Caledon

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Caledon vacation rentals
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1212 Rentals and Airbnb in Caledon

Best family friendly Caledon vacation rentals

Among the 1212 accommodations in Caledon, here are the 4 best family friendly rentals

Spacious, Private Family Friendly 2 Bedroom Home - Caledon
10 3 reviews
Caledon
22/07 – 26/07
$515/nighttotal: $2060 (4 )

Spacious, Private Family Friendly 2 Bedroom Home

2 4
apartment , Caledon East
This Caledon East holiday home is situated 4.3km from The Old Pro Driving Range and within 9.7km of both Camden Dog Park and the Williams Mill Visual Arts Centre.
This 232 square metre property offers two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, laundry facilities, a fireplace, and a smart TV.
Executive 5br-4bath Detached Bramp/miss Border - Caledon
9.8 14 reviews
Caledon
22/07 – 26/07
$1013/nighttotal: $4052 (4 )

Executive 5br-4bath Detached Bramp/miss Border

5 4
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.
Luxury, Home Away From Home. - Caledon
Caledon
22/07 – 26/07
$719/nighttotal: $2876 (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.
Cozy 3br Caledon Bsmt Suite W/ Private Access & Basketball Courtnear Brampton! - Caledon
8.4 11 reviews
Caledon
22/07 – 26/07
$352/nighttotal: $1408 (4 )

Cozy 3br Caledon Bsmt Suite W/ Private Access & Basketball Courtnear Brampton!

3 4
apartment , Toronto
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.

Best Caledon vacation rentals with parking

Luxury 5-bed Home W/ Office & 5 Baths | Peaceful Caledon Escape - Caledon
10 1 review
Caledon
25/08 – 27/08
$751/nighttotal: $1502 (2 )

Luxury 5-bed Home W/ Office & 5 Baths | Peaceful Caledon Escape

5 2
apartment , Caledon East
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.
The Cinema House: 98" Theater I Near Airport I Bbq I Luxury Home - Caledon
10 2 reviews
Caledon
21/06 – 28/06
$666/nighttotal: $4662 (7 )

The Cinema House: 98" Theater I Near Airport I Bbq I Luxury Home

3 6
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.
The Grassy Oasis - Garden Suite | King Bed | Detached | Self Contained - Caledon
10 1 review
Caledon
07/07 – 08/07
$353/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.
Swimming Pool ~Hot Tub ~Pool Table ~Firepit ~Bbq - Caledon
9.3 30 reviews
Caledon
21/06 – 28/06
$895/nighttotal: $6265 (7 )

Swimming Pool ~Hot Tub ~Pool Table ~Firepit ~Bbq

1 6
apartment , Caledon
This spacious estate home is located in Caledon, just 45 minutes from Toronto Pearson Airport and an hour from downtown Toronto. The property has received excellent ratings for its cleanliness, location, and overall user experience.
This six-bedroom house can accommodate up to 12 guests and features a modern design with an open-plan layout. Guests can enjoy a fully equipped kitchen, a family room with two TVs, a basement with a bar table and a convertible billiards/ping pong table, a private backyard with a ravine view, a swimming pool, a gazebo, and a sauna.

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.

Destinations nearby

Best Caledon vacation rentals with a balcony

The Ecstatic Joy Of Heaven - Caledon
Caledon
22/07 – 26/07
$171/nighttotal: $684 (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.
Scenic Casa Azul Retreat With Jacuzzi & Gazebo - Caledon
Caledon
22/07 – 26/07
$562/nighttotal: $2248 (4 )

Scenic Casa Azul Retreat With Jacuzzi & Gazebo

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.
Charming Log Home - 25 Private Acres In Caledon - Caledon
10 1 review
Caledon
25/08 – 27/08
$719/nighttotal: $1438 (2 )

Charming Log Home - 25 Private Acres In Caledon

3 2
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.
Hockley Valley Resort - Caledon
8.1 1501 reviews
Caledon
02/07 – 02/08
$1003/nighttotal: $31093 (31 )

Hockley Valley Resort

2 3
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.

Best Caledon vacation rentals with air conditioning

Charming Studio Retreat • Heated Pool Available - Caledon
9.9 52 reviews
Caledon
25/08 – 27/08
$264/nighttotal: $528 (2 )

Charming Studio Retreat • Heated Pool Available

1 2
apartment , Caledon
This studio apartment is located on top of the Niagara Escarpment in Caledon Hills, just a short distance from numerous hiking trails, award-winning golf courses, and scenic routes. This accommodation has received excellent ratings for its location, cleanliness, and overall user experience.
The studio is perfect for couples or small families with a comfortable bed and a Murphy bed for additional sleeping space. It offers a fully equipped kitchen, access to a heated pool (for an extra fee), laundry facilities after the 3rd night, and a private garden with stunning views of the surrounding countryside.
Caledon Getaway - Caledon
9.8 35 reviews
Caledon
25/08 – 27/08
$186/nighttotal: $372 (2 )

Caledon Getaway

1 2
apartment , Caledon East
This basement flat is located in Caledon East, just a short drive from the Caledon Trailway and the charming Caledon Village. It has consistently received excellent ratings for cleanliness, location, and user experience, making it a popular choice for travellers.
The self-contained apartment comfortably accommodates up to four guests and features a fully equipped kitchen with a fridge, microwave, and stove. Enjoy the convenience of Wi-Fi, IPTV, air conditioning, and a private parking space.
Private Caledon Retreat With Pool & Hot Tub - Caledon
Caledon
02/07 – 02/08
$1981/nighttotal: $61411 (31 )

Private Caledon Retreat With Pool & Hot Tub

1 3
apartment , Caledon
This Caledon flat offers a private resort-style retreat in a peaceful countryside setting, just a few minutes' drive from Orangeville's shops, restaurants, golf courses, and scenic trails.
Boasting five bathrooms and capacity for fourteen guests, this apartment provides a heated swimming pool, hot tub, fitness centre, and a landscaped backyard for outdoor enjoyment, with internet and air conditioning included.
Private Cottage Heated Pool/hottub/games 20 Acre - Caledon
9.5 50 reviews
Caledon
25/08 – 27/08
$1311/nighttotal: $2622 (2 )

Private Cottage Heated Pool/hottub/games 20 Acre

1 2
apartment , Orangeville
This five-bedroom, three-bathroom country house is situated in a tranquil rural setting near Orangeville, Ontario, just 100 kilometres from Toronto, offering easy access to attractions such as Hockley Valley Resort, TPC Toronto Osprey Valley, and Island Lake Conservation Area. The property spans 20 acres and includes a heated outdoor pool, hot tub, games room, and ample space for outdoor activities, accommodating up to 14 guests.
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