Holiday Rentals in Caledon

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Caledon holiday rentals
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Best Holiday rentals and Airbnb offers in Caledon

Browse Holiday Rentals near the Historic Centre in Caledon

Reconnect deeply with your significant other at peaceful holiday rentals for couples in Caledon, offering romantic settings and privacy.

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.
Charming Log Home - 25 Private Acres In Caledon - Caledon
10 71 reviews

Charming Log Home - 25 Private Acres In Caledon

apartment, Caledon East
This apartment is located in Caledon East, a tranquil area on the rolling hills, just 45 minutes from the Greater Toronto Area (GTA). It has received excellent ratings for location, cleanliness, and user experience.
This three-bedroom, two-bathroom home can accommodate up to eight guests. The apartment comes equipped with a modern kitchen, a wood-burning fireplace, two TVs, and a garden, offering a serene setting with nearby trails, a pond, and winter activities like skating and snowshoeing.
Luxury 5-bed Home| 5 Ensuite Bath |Peaceful Escape - Caledon
10 1 review

Luxury 5-bed Home| 5 Ensuite Bath |Peaceful Escape

apartment, Caledon East
This executive detached house in Caledon East offers a peaceful countryside retreat, located minutes from scenic trails and less than 1 hour by car from Toronto.
This spacious, family-friendly residence accommodates up to 10 guests with 5 bedrooms and 5.5 bathrooms, featuring a modern kitchen, air conditioning, Wi-Fi, and on-site parking, ideal for exploring local parks and hiking routes.
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.

Best Caledon holiday rentals with air conditioning

The Loft - Caledon
9.8 33 reviews

The Loft

farm, Adjala-Tosorontio
This farm stay is situated in Adjala-Tosorontio, just 40 kilometres from Woodbine Race Track and 45 kilometres from Pearson International Airport, offering a peaceful rural escape close to major attractions. It has consistently received excellent reviews for its location, cleanliness, and overall experience.
The property comprises a three-bedroom house with one bathroom, comfortably accommodating up to eight guests. Enjoy the unique atmosphere of a working horse farm with over 300 acres of hiking trails nearby, a garden, a BBQ area, and the option of booking a tour of the facilities.
Your Countryside Retreat  Our Passion  ️ Cozy Comfort | Rustic Charm - Caledon
No reviews

Your Countryside Retreat Our Passion ️ Cozy Comfort | Rustic Charm

apartment, Toronto
This apartment in Brampton's Fletcher's Meadow North is a 5-minute drive from Heart Lake Nature Reserve and a 6-minute drive from Lake Cœur, offering convenient access to local attractions within the Greater Toronto Area.
This two-bedroom flat accommodates up to four guests and features a fully equipped kitchen with a fridge and microwave, air conditioning, complimentary Wi-Fi, and on-site parking.
Spacious Cozy 4br Home W/patio Decknear Hospital! - Caledon
9.0 6 reviews

Spacious Cozy 4br Home W/patio Decknear Hospital!

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.
Hockley Riverside Cottage  Loft & Bunkie - Caledon
9.9 184 reviews

Hockley Riverside Cottage Loft & Bunkie

cottage, Orangeville
This charming cottage is located just 15 kilometres from Orangeville, close to Hockley Valley Resort, the Hockley General Store, and Mono Cliffs Provincial Park, offering a peaceful escape by the Nottawasaga River. The property has received excellent ratings for location, cleanliness, and overall user experience.
The cottage has three bedrooms and one bathroom, accommodating up to five guests. Enjoy modern conveniences including a fully equipped kitchen, a wood-burning fireplace, air conditioning, a spa, a garden, and a fire pit for relaxing evenings.

Frequently asked questions about holiday rentals in Caledon

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

    For a first-time visit to Caledon, you shouldn't miss the beautiful Cheltenham Badlands. These unique geological formations are a must-see, and you can also check out the Caledon Trailway, a scenic paved path perfect for cycling or a leisurely stroll.
  • What are the best Airbnb and holiday rentals in Caledon?

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

    If you're looking for a vacation rental in Caledon, the neighbourhood of Palgrave is a great option. It's close to the Caledon Trailway and has a good selection of restaurants and shops. You could also consider the more rural area of Inglewood, which is close to the Cheltenham Badlands and offers a more peaceful atmosphere.
  • What are the most popular Airbnbs in Caledon?

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

    Caledon is full of family-friendly attractions. The Belfountain Conservation Area is a great spot for a picnic or a hike, and the Albion Hills Conservation Area has a playground and a splash pad. For something a little different, check out the Caledon Animal Shelter, where you can meet the animals and learn about adoption.
  • What are the best holiday 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 avoid the crowds and enjoy pleasant weather, perfect for exploring the outdoors.
  • What are the best rentals for families and kids in Caledon?

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

    Caledon has plenty of budget-friendly activities. You can enjoy a free walk along the Caledon Trailway, explore the Cheltenham Badlands, or have a picnic at one of the many parks. For a unique experience, visit the Caledon East Farmers' Market and browse the local produce and crafts.
  • What are the best rentals or Airbnbs with a jacuzzi in Caledon?

  • What are the best restaurants with local dishes in Caledon?

    For a taste of local cuisine, check out The Millcroft Inn. They offer a classic Canadian menu with fresh, seasonal ingredients. If you're looking for something more casual, try the Caledon Hills Golf Club, which has a great restaurant with a view of the course.
  • What are the best walking or cycling routes in Caledon?

    The Caledon Trailway is a great option for both walking and cycling. It's a 42 km paved path that runs through the heart of Caledon, offering scenic views of the countryside. For a shorter walk, try the Bruce Trail, which has several access points in Caledon.
  • Are there pet-friendly attractions in Caledon?

    Yes, there are many pet-friendly attractions in Caledon. The Caledon Trailway is a great place to walk your dog, and many parks and conservation areas are dog-friendly. The Belfountain Conservation Area even has a designated off-leash dog area.
  • What are the benefits of choosing a vacation rental in Caledon?

    Vacation rentals in Caledon offer more space and privacy than a hotel. They often have kitchens and laundry facilities, making them ideal for families or groups. You can also find rentals with unique features like fireplaces or hot tubs, adding to the overall experience.
  • What are the top sports attractions and facilities in Caledon?

    Caledon is a great place for sports enthusiasts. The Caledon Hills Golf Club has a challenging 18-hole course, and there are several other golf courses in the area. For other activities, check out the Caledon Tennis Club or the Caledon Soccer Club.

Popular destinations

Check Out Holiday Rentals with a Balcony in Caledon

Private balconies with city skyline views come as standard at these holiday rentals in Caledon for a lovely start to your day.

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.
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.

Discover Family-Friendly Self-Catering Rentals in Caledon

Getting the holiday rental right makes all the difference for a family trip to Caledon. Find city attractions within easy reach. Start comparing now.

Lakeview Private Suite With Kitchen (Twin Or King) - Caledon
8.6 7 reviews

Lakeview Private Suite With Kitchen (Twin Or King)

house, Adjala-Tosorontio
This self-catering villa, the Lakeview Resort Style Suite (Twin Or King), is situated in Adjala-Tosorontio, within 10km of Legacy Pines Golf Club, Glen Haffy Conservation Area, and Albion Hills Conservation Area.
The one-bedroom, one-bathroom suite sleeps three guests and features a fully equipped kitchen, patio, Smart TV, and is within easy reach of local nature trails.
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.
Gorgeous Cozy Cottage Besides A Bustling Stream, Surrounded By Gorgeous Greenery - Caledon
8.8 19 reviews

Gorgeous Cozy Cottage Besides A Bustling Stream, Surrounded By Gorgeous Greenery

cottage, Orangeville
This Orangeville riverfront cottage, situated 1 km from Hockley Valley Provincial Park and 2.2 km from Hockley Valley Resort, offers a tranquil escape near Theatre Orangeville and Island Lake Conservation Area (within 10 km).
The 65 square metre self-catering property sleeps four guests in one bedroom and one bathroom, featuring a kitchenette, fireplace, WiFi, and access to outdoor barbecue grills and a garden.
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.

Compare Holiday Rentals with Parking in Caledon

Park up and enjoy the city centre. These holiday rentals in Caledon come with a free car park on-site. Start comparing now.

Modern Private Suite | Full Kitchen, Self Check-in - Caledon
9.7 104 reviews

Modern Private Suite | Full Kitchen, Self Check-in

apartment, Orangeville
The Green Lodge - Upper Level Raised Bungalow - Caledon
10 18 reviews

The Green Lodge - Upper Level Raised Bungalow

apartment, Orangeville
Luxury Estate In Caledon On! - Caledon
9.1 36 reviews

Luxury Estate In Caledon On!

apartment, Caledon
Modern 2br Private Suite | Prime Location - Caledon
10 5 reviews

Modern 2br Private Suite | Prime Location

apartment, Caledon East

Explore 5-Star Self-Catering Rentals in Caledon

A city-centre luxury holiday rental or Airbnb in Caledon sets the perfect tone for your stay. Expect 5-star comfort and quality throughout.

Caledon East Retreat - Caledon
10 28 reviews

Caledon East Retreat

apartment, Caledon East

Top Pet-Friendly Holiday Rentals in Caledon

Your dog is as welcome as you are. These pet-friendly holiday rental and Airbnbs in Caledon provide easy access to local dog parks and city walks. See what's available.

Studio Apartment - Caledon
9.7 260 reviews

Studio Apartment

studio, Caledon East
30 Minutes Drive To Pearson Airport - Caledon
8.9 196 reviews

30 Minutes Drive To Pearson Airport

apartment, Caledon
Country Side Greenery - Caledon
9.3 3 reviews

Country Side Greenery

apartment, Orangeville
The Perfect Getaway - Caledon
8.0 6 reviews

The Perfect Getaway

apartment, Orangeville

Choose the Right Holiday Rentals with a Pool in Caledon

Pool access at your holiday rental makes a proper swim in the heart of the city part of your daily routine in Caledon.

Guest Suite In Hockley Valley - Caledon
9.9 72 reviews

Guest Suite In Hockley Valley

apartment, Orangeville
10 Acres Luxury Retreat W/pool & Trail - Caledon
10 1 review

10 Acres Luxury Retreat W/pool & Trail

apartment, Adjala-Tosorontio
Caledon Country Studio Near Trails, Golf & Events - Caledon
9.9 57 reviews

Caledon Country Studio Near Trails, Golf & Events

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

Bright, Modern, A Quiet Retreat On The Hill.

apartment, Caledon

Guest-Favourite Holiday Rentals with a Hot Tub in Caledon

Private hot tub access after a day in the city is one of those details that makes a trip to Caledon truly memorable.

Caledon Trailside Retreat-sleeps 6 - Caledon
10 5 reviews

Caledon Trailside Retreat-sleeps 6

apartment, Caledon
Modern-detached 5 Bedroom100 Spotless-sleeps 13 - Caledon
No reviews

Modern-detached 5 Bedroom100 Spotless-sleeps 13

house, Caledon East
Beautiful Home In Tottenham - Caledon
9.5 73 reviews

Beautiful Home In Tottenham

apartment, Adjala-Tosorontio
The Hockley Hill House -4 Br W/escarpment Views - Caledon
No reviews

The Hockley Hill House -4 Br W/escarpment Views

apartment, Orangeville
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