Find short term rentals in Caledon at the best prices

1403 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Caledon short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Short term and Weekly rentals in Caledon

Best Caledon luxury short term rentals

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.

Best Caledon Short term rentals with a jacuzzi

Among the 1403 accommodations in Caledon, here are the 4 best rentals with a jacuzzi

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.
Swimming Pool ~Hot Tub ~Pool Table ~Firepit ~Bbq - Caledon
9.3 31 reviews

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

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.
Spacious 2-bed Suite With Private Bath & Walk-in Closet In Brampton Shared Home! - Caledon
10 1 review

Spacious 2-bed Suite With Private Bath & Walk-in Closet In Brampton Shared Home!

apartment, Toronto
This riverside flat in Brampton offers a peaceful setting, located 24 kilometres from the Mississauga Convention Centre and 26 kilometres from Heartland Town Centre.
This 149 square metre holiday home accommodates two guests and features a kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a jacuzzi, garden, spa, and parking.
Spacious 2-bed Suite With Private Bath, Mini Fridge, Tv & Walk-in Closet In Brampton Shared Home - 4 Baths, Full Kitchen, Wifi, Laundry & Deck - Near Go Station, Great For Groups! - Caledon
10 1 review

Spacious 2-bed Suite With Private Bath, Mini Fridge, Tv & Walk-in Closet In Brampton Shared Home - 4 Baths, Full Kitchen, Wifi, Laundry & Deck - Near Go Station, Great For Groups!

B&B, Toronto
This Brampton guest house is located 17.7 kilometres from Toronto Pearson International Airport, 13.8 kilometres from the Mississauga Convention Centre, and approximately 30-32 kilometres from Vaughan Mills Shopping Centre, Canada's Wonderland and the Aviva Centre.
This spacious B&B offers 149 square meters of living space, accommodating up to three guests with one master bedroom, two bathrooms, a shared kitchen, living room, patio, and an on-site hot tub, complemented by complimentary private parking and free Wi-Fi.

Frequently Asked Questions about short term rentals in Caledon

  • Which top landmarks you shouldn't miss in Caledon?

    Caledon has some lovely landmarks. The Belfountain Conservation Area is a great place to go for a walk in nature, and the Cheltenham Badlands are unique geological formations worth seeing. For history buffs, the Albion Hills Conservation Area has a rich history and you can see the remains of an old mill.
  • What are the best short term rentals in Caledon?

    Among the short term rentals in Caledon, Mono — Cabin In The Woods Experience, Luxury Modern Two Bedrooms Basement Apartment and Erin Cabin Getaway And Bunkie are the most popular ones.

  • What kind of weather can travelers expect in Caledon?

    Caledon has four distinct seasons. Summers are warm and humid, with temperatures reaching up to 30°C. Winters can be cold and snowy, with temperatures often dropping below freezing. Spring and autumn are mild and pleasant.
  • What are the best short term rentals with a pool in Caledon?

  • What are the most popular festivals and events in Caledon?

    Caledon has a number of popular events throughout the year. The Caledon Fair is a big one, taking place in August, and the Caledon Village Christmas Market is a festive favourite in December. There are also many smaller events and festivals throughout the year.
  • What are the best short term rentals with a jacuzzi in Caledon?

  • Are there any famous stadiums or sports arenas in Caledon?

    There aren't any major stadiums or sports arenas in Caledon, but there are a few smaller venues like the Caledon Community Complex that host local sporting events.
  • What are the best short term rentals for families and kids in Caledon?

  • What notable natural landmarks are near Caledon?

    Caledon is surrounded by some beautiful natural landmarks. The Credit River flows through the area, and there are many great hiking trails and parks to explore. The Bruce Trail, a famous hiking trail, runs through the area.
  • What part of Caledon is ideal for finding lodging?

    The most popular areas for lodging in Caledon are the towns of Bolton and Palgrave. There are a good selection of hotels and bed and breakfasts in these areas, and they're close to many attractions and amenities.

Popular destinations

Best family friendly Caledon Short term rentals

Among the 1403 accommodations in Caledon, here are the 4 best family friendly rentals

Your Group`s Headquarters · Sleeps 12 · Every Gta Venue An Easy Drive - Caledon
No reviews

Your Group`s Headquarters · Sleeps 12 · Every Gta Venue An Easy Drive

apartment, Caledon East
This four-bedroom, four-bathroom apartment in Brampton, conveniently located near Toronto Pearson International Airport (approximately 30km away) and Downtown Toronto (distance unspecified), offers easy access to shopping at Georgetown Market Place and recreational facilities such as Century Gardens Arena.
Sleeping up to 16 guests, this self-catering property boasts proximity to The Old Pro Driving Range and the Lake Nature Reserve (distances unspecified), with pets welcome.
Charming Log Home - 25 Private Acres In Caledon - Caledon
10 81 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.
Modern Retreat With Loft & Spa-like Jacuzzi Tub - Caledon
8.0 3 reviews

Modern Retreat With Loft & Spa-like Jacuzzi Tub

apartment, Caledon East
This modern flat is situated in Brampton, providing convenient access to SilverCity Brampton Cinemas and Bowlero Brampton, both within 5 kilometres, as well as Heart Lake Conservation Area and Claireville Conservation Area.
This spacious 260 square metre residence accommodates up to six guests across four bedrooms and three bathrooms, featuring a kitchen with essential appliances, air conditioning, a terrace, garden, parking, and a spa-inspired jacuzzi tub for relaxation.
Lovely Cozy Apartment - Caledon
9.6 33 reviews

Lovely Cozy Apartment

apartment, Toronto
This Brampton apartment, situated 12km from Toronto Pearson International Airport and 19km from Canada's Wonderland, offers convenient access to major attractions.
The 800 square metre property boasts one bedroom, one bathroom, sleeps three guests, and includes free Wi-Fi, private parking, a fully equipped kitchen, and a flat-screen TV with streaming services.

Best Caledon lodging with parking

Spacious 2 Bedrooms3 Beds  Free Parking Brampton - Caledon
9.6 64 reviews

Spacious 2 Bedrooms3 Beds Free Parking Brampton

B&B, Toronto
This Toronto apartment, ideal for families or groups of up to four, offers a private entrance and free parking, likely situated in a suburban area of Toronto, its precise location unspecified but suggesting proximity to major roadways.
The self-catering property features a spacious layout including two bedrooms, a dedicated workspace, living room, dining room, full kitchen, in-unit laundry, and a bathroom with a bathtub and shower.
Keppel Circle Residence - Caledon
No reviews

Keppel Circle Residence

apartment, Caledon East
Apartment to rent. This accommodation is based in Caledon East.
Facilities and services include a washing machine, a wheelchair friendly access and air conditioning. Take advantage of the Free Parking with this accommodation.
Stylish Suite@professors Lake & Brampton Civc Hosp - Caledon
9.9 82 reviews

Stylish Suite@professors Lake & Brampton Civc Hosp

B&B, Toronto
This private apartment is located in a quiet neighbourhood in Brampton, just 3 kilometres from Professor's Lake, 15 minutes from Brampton Civic Hospital and 5 minutes from public transport. The property has received excellent ratings for its cleanliness, location and overall experience.
The apartment has one bedroom and one bathroom, comfortably accommodating two guests. The suite features a modern and traditional design, a fully equipped kitchen, a dedicated workspace, and a spacious bedroom with an electric fireplace.
Stunning  Luxury Furnished 2bedroom And 2washroom Private Basement Apartment - Caledon
8.6 4 reviews

Stunning Luxury Furnished 2bedroom And 2washroom Private Basement Apartment

apartment, Caledon East
This Brampton apartment, near The Old Pro Driving Range (3.2km) and within 9.6km of several parks including Camden Dog Park and Eldorado Park, offers convenient access to local attractions.
This 93 square metre, two-bedroom, two-bathroom dwelling sleeps four guests and includes free Wi-Fi, parking, a fully equipped kitchen, and on-site laundry facilities; housekeeping is available on request.
©2026 cozycozy.com