Villas and Holiday homes in Caledon

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Caledon holiday homes
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252 Villa rentals in Caledon

Best Caledon villas and holiday homes with a pool

Among the 252 accommodations in Caledon, here are the 4 best villas and holiday homes with a pool

Caledon East Retreat - Caledon
10 30 reviews

Caledon East Retreat

house, Caledon East
The Caledon Retreat is located in Caledon East, just a short drive from the charming downtown area and within easy reach of scenic hiking and biking trails. The property has received excellent ratings for location, cleanliness and user experience.
This seven-bedroom, five-bathroom home can comfortably accommodate up to 12 guests. The retreat offers a range of amenities, including a swimming pool, Jacuzzi, sauna, fitness centre, and a spacious garden, providing plenty of opportunities for relaxation and recreation.
Ballo - Guesthouse - Caledon
9.8 9 reviews

Ballo - Guesthouse

house, Orangeville
This private, newly renovated suite in Orangeville offers a separate entrance and is located in a quiet residential area, just 1.5 kilometres from downtown shops, Theatre Orangeville, Island Lake trails, and Hockley Valley skiing.
This modern accommodation for two features a fully-equipped kitchen with quartz counters, a double bedroom, a spa-style bathroom with a glass shower, and provides internet access, making it ideal for couples or remote workers seeking mid-term stays with easy access to local attractions and outdoor activities.
Stunning Family Retreat, 1hr From To, Sleeps 15 - Caledon
10 66 reviews

Stunning Family Retreat, 1hr From To, Sleeps 15

bungalow, Orangeville
This five-bedroom bungalow is situated in Mono, just under an hour's drive from Toronto and 16 kilometres from Hockley Valley Ski Resort.
The property offers a range of amenities including a swimming pool, hot tub, fitness centre, and a spacious dining area that can accommodate up to 16 guests, making it ideal for large families or groups.
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 family friendly Caledon villas and holiday home

Among the 252 accommodations in Caledon, here are the 4 best family friendly villas and holiday homes

Guest House By Canterra Stays · Not A Basement - Caledon
10 11 reviews

Guest House By Canterra Stays · Not A Basement

house, Toronto
This private, above-ground coach house in Toronto's Vales of Castlemore North offers convenient access to the city and airport.
This modern suite accommodates up to three guests with one bedroom, a full kitchen featuring a fridge, freezer, and microwave, air conditioning, internet, parking, and an EV-friendly Tesla charger available for an additional fee.
Lakeview Private Suite With Kitchen (Twin Or King) - Caledon
8.6 8 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.
Globalstay. Modern 3 Bedroom House In Brampton - Caledon
10 1 review

Globalstay. Modern 3 Bedroom House In Brampton

house, Caledon East
This family-friendly detached house is located in Brampton, a district within the greater Caledon region, offering convenient access to local amenities.
This 177 square meter property features a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, complimentary Wi-Fi, and on-site parking, with select rooms offering a balcony or terrace.
Private Hockley Valley Farmhouse - Caledon
9.7 30 reviews

Private Hockley Valley Farmhouse

gîte, Orangeville
This three-bedroom farmhouse is located in Hockley Valley, just a short drive from Orangeville, offering easy access to the Bruce Trail, the Hockley Valley Conservation Area, and a variety of local attractions. The property enjoys excellent user, location, and cleanliness ratings, making it a top choice for travellers.
The farmhouse comfortably accommodates up to seven guests and features a modern kitchen, a wood-burning fireplace, and super-fast Wi-Fi. Guests can enjoy a secluded country setting, access to nature, nearby attractions, and a range of adventurous activities, ensuring a memorable stay.

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Best Caledon villas and holiday homes 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.
Ligero Townhouse Entire Four Bedrooms Home - Caledon
No reviews

Ligero Townhouse Entire Four Bedrooms Home

house, Orangeville
Ligero Townhouse is located in Orangeville, Ontario, offering convenient access to the town's centre, local shops, restaurants, and parks, with the downtown area situated less than 1 kilometre away. This 185 square meter, three-bedroom townhouse accommodates up to six guests and features a fully equipped kitchen, air conditioning, a garden, and parking, making it suitable for families and groups.
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.
186 M² House ∙ 3 Bedrooms ∙ 6 Guests - Caledon
No reviews

186 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Orangeville
This three-bedroom townhouse is located centrally in Orangeville, Ontario, providing convenient access to the town's downtown area, local shops, restaurants, parks, and nearby attractions.
This spacious accommodation spans 185 square meters and accommodates up to six guests, featuring a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, and a terrace, with parking available.

Best Caledon villas and holiday homes with a garden

Cozy Brampton Stay Near Mount Pleasant Go - Caledon
8.0 1 review

Cozy Brampton Stay Near 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.
Island Lake Guest House - Caledon
9.9 64 reviews

Island Lake Guest House

house, Orangeville
This studio apartment is located in a peaceful residential area in Orangeville, just a short walk from the Island Lake Conservation Area and less than 1 kilometre from the lake's 9km lakeside loop trail. The studio has received excellent ratings for its cleanliness, location, and overall experience.
This self-catering studio accommodates up to 3 guests and has a fully equipped kitchen, a private patio with a BBQ, and a cedar outdoor shower. Guests can enjoy a tranquil setting, close proximity to nature, and access to a smart TV and Wi-Fi.
Character-filled Farm Guest House On 8 Acres - Caledon
9.9 81 reviews

Character-filled Farm Guest House On 8 Acres

farm, Adjala-Tosorontio
This charming gîte is located in Adjala-Tosorontio, 45km north of Toronto, close to Tottenham and Palgrave, and 20km from Orangeville or Alliston. It has consistently received excellent ratings for its location, cleanliness, and user experience.
The gîte is a 2-bedroom, 1-bathroom property that can accommodate up to 4 guests. It features a spacious living area, a fully equipped kitchen, and a private garden, as well as access to a working hobby farm with a variety of animals. Guests can enjoy hiking trails on the surrounding 400 acres of conservation land, or visit nearby attractions like Hockley Valley Resort and Adamo Winery.
A Private & Stylish Urban Studio - Caledon
9.9 163 reviews

A Private & Stylish Urban Studio

studio, Orangeville
This charming bed and breakfast is situated in central Orangeville, just 0.7km from Theatre Orangeville and 2.1km from Island Lake Conservation Area, offering a peaceful retreat close to local attractions. The accommodation has consistently received excellent ratings for its cleanliness, location and overall experience.
This one-bedroom property, spanning 59 square metres, comfortably accommodates two guests. Enjoy a range of amenities, including a fully equipped kitchen, a private terrace, a garden, a jacuzzi, and barbecue facilities.
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