Villas and Holiday homes in Caledon

252 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Caledon holiday homes
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Mono Springs - Dream Country Escape W Pool/hot Tub - Caledon
9.8 51 reviews

Mono Springs - Dream Country Escape W Pool/hot Tub

house, 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.
House With A Pool In Caledon - Caledon
No reviews

House With A Pool In Caledon

house, 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.
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.
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.

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

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.
Cozy Brampton Stay Near Mount Pleasant Go - Caledon
No reviews

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.
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.
Luxury - Sleeps 10 - Smart Home - Ps5 - 85 Oled - Caledon
No reviews

Luxury - Sleeps 10 - Smart Home - Ps5 - 85 Oled

house, Caledon East
This four-bedroom, four-bathroom luxury dwelling in Caledon East is situated 20.9 kilometres from Toronto Pearson International Airport, 15.9 kilometres from the Mississauga Convention Centre, and 33.8 kilometres from Canada's Wonderland.
This spacious property, covering 242 square metres, offers accommodation for up to 10 guests and includes a sauna, spa bath, and smart home technology.

Frequently asked questions about villa rentals in Caledon

Popular destinations

Best Caledon villas and holiday homes with parking

Executive 5br-4bath Detached Bramp/miss Border - Caledon
No reviews

Executive 5br-4bath Detached Bramp/miss Border

house, Toronto
Holiday house to rent. This accommodation is located in Toronto.
Services and facilities: a terrace, free parking and a fridge.
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.
Ligero Townhouse Entire Four Bedrooms Home - Caledon
No reviews

Ligero Townhouse Entire Four Bedrooms Home

house, Orangeville
Ligero Townhouse is located in Orangeville, 3.9 kilometres from Theatre Orangeville and 48.3 kilometres from Mississauga Convention Centre.
This 186 square metre holiday home offers air conditioning, free WiFi, a private entrance, and outdoor seating for up to six guests, with private parking available.
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.

Best Caledon villas and holiday homes with a garden

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.
The Enchanted Cottage - Caledon
9.7 14 reviews

The Enchanted Cottage

cabin, Orangeville
This charming cottage is situated close to the centre of Orangeville, offering easy access to the town's amenities and attractions. The surrounding area is peaceful and green, with a lively stream flowing nearby.
The cottage has one bathroom and can comfortably accommodate up to four guests. It is equipped with a kitchen, air conditioning, parking, and internet access, providing all the essentials for a relaxing stay.
3 Separate Sleeping Rooms On 23-acre Horse Farm - Caledon
10 59 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.
Perfect 10 Acres Private Quiet Property For Small Events & Family Gatherings - Caledon
10 1 review

Perfect 10 Acres Private Quiet Property For Small Events & Family Gatherings

cottage, Caledon
Vintage Cottage Retreat, a 4-bedroom property sleeping 14, is situated in Caledon, Ontario, approximately 72km from Yorkdale Shopping Centre and conveniently located near Forks of the Credit Provincial Park and the Bruce Trail.
This 3,700 sq ft holiday home boasts a full kitchen with microwave and dishwasher, 4 bathrooms, a solarium, terrace, garden, parking, air conditioning, and a wood-burning fireplace; it also offers 10 acres of land ideal for camping, stargazing, and small events.
©2026 cozycozy.com