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

House With A Pool In Caledon - Caledon
Caledon
22/07 – 26/07
$447/nighttotal: $1788 (4 )

House With A Pool In Caledon

1 4
apartment , Caledon
This holiday home is located in Caledon, just a short drive from Starbucks and Hockley Valley, offering easy access to local amenities and attractions. The property sits on a half-acre plot, providing privacy and ample space for gatherings.
The house has four bedrooms and one bathroom, sleeping up to ten guests. Enjoy the above-ground pool, outdoor fire pit, and ample parking, as well as a fireplace, pool table, and spacious kitchen.
Beautiful Getaway In Orangeville - Caledon
10 56 reviews
Caledon
22/07 – 26/07
$288/nighttotal: $1152 (4 )

Beautiful Getaway In Orangeville

1 4
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.
Hidden Gem - Caledon
10 1 review
Caledon
22/06 – 29/06
$229/nighttotal: $1603 (7 )

Hidden Gem

1 2
apartment , Toronto
This Brampton apartment, situated approximately 5km from the Lester B. Pearson Memorial Theatre and within 5km of Donald M. Gordon Chinguacousy Park, offers easy access to local attractions.
This one-bedroom, one-bathroom flat sleeps two guests and includes free parking, in-unit laundry, a fully equipped kitchen with oven and microwave, free Wi-Fi, and a smart TV; nearby amenities include Bowlero Brampton and the Historic Bovaird House.
Basement Appartment - Caledon
Caledon
22/06 – 29/06
$331/nighttotal: $2317 (7 )

Basement Appartment

1 2
house , Toronto
This spacious 2-bedroom basement flat is located in a family-friendly district of Toronto, offering a large garden and a bright lookout basement with convenient access from the garden.
This accommodation comfortably sleeps 4 guests, featuring two bedrooms, two bathrooms, a kitchen with a fridge and microwave, air conditioning, Wi-Fi, and an on-site fitness centre.

Best Caledon vacation rentals with parking

Modern 2 Bedroom Suite Near Airport Free Parking - Caledon
Caledon
22/06 – 29/06
$181/nighttotal: $1267 (7 )

Modern 2 Bedroom Suite Near Airport Free Parking

1 2
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.
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.
Spacious Cozy 4br Home W/patio Deck—near Hospital! - Caledon
8.0 3 reviews
Caledon
19/06 – 21/06
$414/nighttotal: $828 (2 )

Spacious Cozy 4br Home W/patio Deck—near Hospital!

4 2
apartment , Orangeville
This four-bedroom house in Orangeville is situated 800 metres from Headwaters Health Care Centre and 8 kilometres from Mount Alverno Luxury Resorts, offering convenient access to local amenities and attractions including Island Lake Conservation Area and Broadway boutiques.
This spacious property, ideal for families and groups of up to ten, features air conditioning, a jacuzzi, a garden, a fitness centre, parking, a fully equipped kitchen, a patio with a BBQ, and complimentary Wi-Fi.
Guesthouse Hideaway In Caledon - Caledon
Caledon
22/06 – 29/06
$433/nighttotal: $3031 (7 )

Guesthouse Hideaway In Caledon

4 2
apartment , Toronto
This B&B is located in Caledon, a district outside Toronto, offering proximity to local landmarks such as Bovaird House and Devereaux House, and markets including Downey's Farm Market and Brampton Farmers' Market.
This accommodation provides exclusive use of a spacious 3-bedroom, 3-bathroom walkout basement suite with a private entrance, featuring two bedrooms with ensuite bathrooms and private living areas, high 9-foot ceilings, abundant natural light, and is situated on a peaceful ravine lot with access to outdoor activities like hiking and mountain biking.

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 Hockley Hideaway, Sharing Our Unique Property For Your Unique Experiences️ - Caledon
10 46 reviews
Caledon
25/08 – 27/08
$1689/nighttotal: $3378 (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.
The Cinema House: 98" Theater I Near Airport I Bbq I Luxury Home - Caledon
10 2 reviews
Caledon
22/06 – 29/06
$701/nighttotal: $4907 (7 )

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

3 2
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.
Perfect Group Getaway Large House With Style - Caledon
Caledon
21/06 – 28/06
$2195/nighttotal: $15365 (7 )

Perfect Group Getaway Large House With Style

6 6
apartment , Bolton
This spacious six-bedroom, six-bathroom Caledon holiday home in Bolton offers ample room for up to 16 guests and boasts extensive front and back gardens, perfect for outdoor events, with the option of a walkout basement suite providing additional living space. Situated near the Claireville and Heart Lake Conservation Areas, this property provides convenient access to outdoor pursuits, with Landmark Cinemas Caledon, Copper Creek Golf Club, and the Zanchin Automotive Soccer Centre all within a short drive.
Hockley Valley Resort - Caledon
8.1 1500 reviews
Caledon
25/08 – 27/08
$414/nighttotal: $828 (2 )

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.

Best Caledon vacation rentals with air conditioning

Lux Basement Apartment Getaway - Caledon
Caledon
22/06 – 29/06
$215/nighttotal: $1505 (7 )

Lux Basement Apartment Getaway

1 2
apartment , Caledon East
This stylish 1-bedroom basement flat in Brampton offers convenient access to Brampton Farmers' Market and Georgetown Market Place, and is situated within 10 kilometers of Heart Lake Conservation Area and Terra Cotta Conservation Area.
This flat accommodates up to 4 guests with a queen bed and sofa bed, featuring a fully equipped kitchen, air conditioning, Wi-Fi, and private entrance, making it ideal for work trips or weekend breaks.
Peaceful Retreat By Osprey Golf & Equestrian Park - Caledon
9.7 53 reviews
Caledon
22/07 – 26/07
$383/nighttotal: $1532 (4 )

Peaceful Retreat By Osprey Golf & Equestrian Park

1 4
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.
The Refresh Stream - Caledon
Caledon
22/06 – 29/06
$185/nighttotal: $1295 (7 )

The Refresh Stream

2 2
apartment , Toronto
This Brampton basement flat, a 25-30 minute drive (approx. 32-39km) from Square One Shopping Centre and 15 minutes (approx. 16km) from Bramalea City Centre, offers convenient access to Toronto Pearson International Airport (YYZ).
Sleeping up to six guests, this two-bedroom, one-bathroom self-contained apartment features two fireplaces, a fully equipped kitchen including a conventional oven and toaster oven, air conditioning, parking, and internet access; nearby amenities include walking trails and Canada's Wonderland.
Hockley Valley Cozy Cottage With Waterfront Access! - Caledon
Caledon
25/08 – 27/08
$328/nighttotal: $656 (2 )

Hockley Valley Cozy Cottage With Waterfront Access!

2 2
apartment , Orangeville
This two-bedroom flat in Mono offers private waterfront access to a river, located approximately 6.1 kilometres from Orangeville's amenities and cultural attractions, including Theatre Orangeville and the Dufferin County Museum & Archives.
This property accommodates up to four guests and features a fireplace, outdoor gazebo, and is conveniently situated near outdoor recreation at Hockley Valley Resort and Mono Cliffs Provincial Park.
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