This family-friendly Bolton basement flat, located in a quiet neighbourhood approximately 48 kilometres from Pearson International Airport and 16 kilometres from Husky IMS, offers a private entrance and excellent guest reviews. The two-bedroom, one-bathroom self-catering apartment sleeps four, includes a fully equipped kitchen with fridge, freezer and microwave, air conditioning, parking, and internet access, providing comfortable accommodation for families or small groups.
Caledon
22/07 – 26/07
$233/nighttotal: $932 (4 )
Ravine Lot Spacious 2 Bedrooms + Den Legal Basement Apartment
3 4
apartment , Caledon East
This newly built basement flat in Brampton's Alloa neighbourhood offers a peaceful escape, situated approximately 48 kilometres from Pearson Airport and a short drive from the Great War Flying Museum and Historic Bovaird House. This 3-bedroom, 1-bathroom flat accommodates up to six guests, featuring two queen-sized bedrooms with wardrobes, a spacious living area with a leather sectional, a fully equipped kitchen, and a dedicated children's play area, all with complimentary Wi-Fi.
9.9 235 reviews
Caledon
22/07 – 26/07
$258/nighttotal: $1032 (4 )
Rural Estate Coach House Apartment
1 4
apartment , Orangeville
This two-bedroom apartment is situated in a secluded forest setting just 5 kilometres outside of Orangeville, offering a peaceful escape from the hustle and bustle of the town. It has consistently received excellent ratings for its cleanliness, location and overall experience. The apartment is spacious and flexible, accommodating up to four guests. It features a well-equipped kitchen, a private patio and a dedicated barbecue, perfect for enjoying the outdoors. The apartment also offers access to a gazebo and is close to a range of attractions including the Bruce Trail, Hockley Valley Ski Resort and various art studios, restaurants and antique stores.
9.1 23 reviews
Caledon
02/10 – 03/10
$76/nightfor 1 night
Pvt Bedroom Bathroom
1 2
B&B , Caledon
This B&B is conveniently located on the main road in Caledon, just a short drive from the Caledon Trailway, the Cheltenham Badlands, and the Caledon East Farmers Market. It has received very good ratings for its cleanliness, location, and overall experience. The guest house offers a private bedroom and bathroom with a separate entrance, providing a comfortable and independent stay for up to two guests. Guests can enjoy amenities like a shared kitchen, free Wi-Fi, air conditioning, and parking, making it a convenient and enjoyable base for exploring the area.
Caledon
21/06 – 28/06
$267/nighttotal: $1869 (7 )
Beautiful Upstairs Unit Near Transit & Shopping
3 6
apartment , Toronto
This three-bedroom flat is located in Brampton West, offering easy access to Eldorado Park and a 14-kilometre drive to Square One Shopping Centre. This upstairs property accommodates six guests and features air conditioning and internet, with proximity to shopping, transit, parks, and schools.
9.0 105 reviews
Caledon
25/08 – 27/08
$76/nighttotal: $152 (2 )
Lovely Private 1 Bedroom Apartment W Pvt Entrance
1 2
apartment , Caledon
This charming bed and breakfast is located just off Highway 10 in Caledon, a short 40-minute drive from Toronto Pearson Airport, making it an ideal base for exploring the surrounding countryside. It has consistently received excellent ratings for its cleanliness, location, and overall experience. The accommodation offers a private entrance and key, ensuring a peaceful stay for up to two guests. Amenities include Wi-Fi, air conditioning, parking, and a modern, comfortable interior, perfect for those seeking a relaxing escape surrounded by nature.
9.7 163 reviews
Caledon
07/07 – 08/07
$198/nightfor 1 night
R3 Suites In The Heart Of Alton. Frontunit
1 2
apartment , Caledon
This one-bedroom apartment is located in the charming hamlet of Alton, just a short walk from the historic Alton Mill and scenic trails. It has consistently received excellent ratings for location, cleanliness, and overall user experience. The apartment comfortably accommodates up to four guests and features a queen-sized bed, a pull-out sofa, and a small kitchenette. Guests can enjoy a private entrance, a quiet location, a garden, parking, internet access, air conditioning, and welcome treats.
Caledon
21/06 – 28/06
$236/nighttotal: $1652 (7 )
Luxury Executive Suite In Valley
3 6
apartment , Toronto
This Brampton suite is situated in the Castlemore community, a mere 8 kilometres from Pearson Airport and 800 metres from Brampton Civic Hospital, offering convenient access for travellers. This luxury three-bedroom dwelling accommodates up to six guests, featuring air conditioning, Wi-Fi, and parking for two vehicles, with exclusive living, dining, and kitchen areas for a private stay.
9.6 26 reviews
Caledon
25/08 – 27/08
$210/nighttotal: $420 (2 )
A Charming, Rustic 150 Year Old Carriage House
1 2
B&B , Orangeville
This charming Carriage House is situated in Orangeville, just 47 kilometres from the Mississauga Convention Center and 48 kilometres from the Vaughan Mills Shopping Centre. It offers a peaceful retreat with excellent user, location, and cleanliness ratings. The guest house spans 93 square metres and comfortably accommodates two guests. It features a spacious living room, bedroom, and a fully equipped kitchen, along with a relaxing fireplace, a private garden, and a terrace for outdoor dining.
9.8 224 reviews
Caledon
02/10 – 03/10
$104/nightfor 1 night
Studio Apartment
1 2
apartment , Caledon East
This Caledon East studio apartment offers excellent location, within easy walking distance of local shops, cafes, and parks. The self-contained unit sleeps two guests and features two bathrooms, air conditioning, parking, and internet access; nearby attractions and community events provide ample opportunities for exploration.
Caledon
02/07 – 02/08
$250/nighttotal: $7750 (31 )
Cozy & Modern Getaway In Tottenham, New Tecumseth
1 3
apartment , Tottenham
This two-bedroom flat in Tottenham offers convenient road access to the New Tecumseth and Simcoe County region, with the Tottenham Conservation Area, golf courses, and scenic walking trails within easy reach. This comfortable apartment accommodates up to three guests and features air conditioning, a swimming pool, and a fully equipped kitchen with a fridge, microwave oven, and dishwasher, providing a relaxing home-away-from-home experience.
10 40 reviews
Caledon
07/07 – 08/07
$207/nightfor 1 night
The Woodland Walkout
1 2
apartment , Toronto
This Toronto basement flat offers a private entrance and is conveniently located near local amenities, though precise distances to landmarks are unavailable. The self-contained apartment sleeps two guests and features a full kitchen, modern bathroom with rain shower, two TVs, private outdoor seating, free Wi-Fi, and free parking.
Best Caledon luxury short term rentals
Caledon
22/07 – 26/07
$237/nighttotal: $948 (4 )
Gifted Beautiful Home
2 4
B&B , Caledon East
Gifted Beautiful Home, a bed and breakfast in Brampton, is situated approximately 15.1 kilometres from the Mississauga Convention Centre and 32.2 kilometres from Vaughan Mills Shopping Centre. This accommodation offers air-conditioned rooms with free Wi-Fi, private parking, and en-suite bathrooms, located 17.7 kilometres from Toronto Pearson International Airport.
Best Caledon Short term rentals with a jacuzzi
Among the 1043 accommodations in Caledon, here are the 4 best rentals with a jacuzzi
9.5 71 reviews
Caledon
02/10 – 03/10
$1031/nightfor 1 night
Beautiful Home In Tottenham
1 2
apartment , Adjala-Tosorontio
This spacious apartment is located in Adjala-Tosorontio, just a short distance from Highways 9 and 50, making it easy to explore the surrounding area. It has received excellent ratings for cleanliness, location and user experience. The property has four bedrooms and three bathrooms, comfortably accommodating up to ten guests. Amenities include air conditioning, parking, internet access, a fully equipped kitchen with a fridge, and a large outdoor space perfect for enjoying the fresh air and relaxing in the peaceful surroundings.
Caledon
02/07 – 02/08
$1981/nighttotal: $61411 (31 )
Private Caledon Retreat With Pool & Hot Tub
1 3
apartment , Caledon
This Caledon flat offers a private resort-style retreat in a peaceful countryside setting, just a few minutes' drive from Orangeville's shops, restaurants, golf courses, and scenic trails. Boasting five bathrooms and capacity for fourteen guests, this apartment provides a heated swimming pool, hot tub, fitness centre, and a landscaped backyard for outdoor enjoyment, with internet and air conditioning included.
Caledon
02/07 – 02/08
$3412/nighttotal: $105772 (31 )
Luxury, 4-bed House - Near Osprey Gc For Cdn Open
1 3
apartment , Caledon
This Caledon property, situated in a peaceful neighbourhood, offers easy access to local attractions within a short driving distance, its precise location requiring further specification for accurate distance calculations to landmarks. This 2700 sq ft (approximately 250 sq m) luxury dwelling boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a golf practice area, hot tub, and a basement recreation area with fitness equipment.
9.3 57 reviews
Caledon
22/07 – 26/07
$1015/nighttotal: $4060 (4 )
Charming And Peaceful Retreat With Hot Tub
1 4
apartment , Caledon
This six-bedroom Caledon house, sleeping up to twelve guests, is situated in a peaceful neighbourhood, approximately 14km from the TPC Toronto Osprey Valley Golf Course, 9km from Hockley Valley Resort, and within easy driving distance of other attractions including Caledon Ski Club and Island Lake Conservation Area. The property boasts a fully equipped kitchen with dishwasher and wine fridge, a spacious dining room, three renovated bathrooms, a hot tub, and a large garden, perfect for families or groups seeking a self-catering base for exploring Caledon's amenities.
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 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?
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.
Destinations nearby
Best family friendly Caledon Short term rentals
Among the 1043 accommodations in Caledon, here are the 4 best family friendly rentals
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.
8.8 1061 reviews
Caledon
07/07 – 08/07
$161/nightfor 1 night
Newton Villa
1 2
B&B , Bolton
Newton Villa is a bed and breakfast located in Brampton, about 12 kilometres from Wild Water Kingdom and 19 kilometres from Canada's Wonderland. It has received very good ratings for its location, cleanliness and overall experience. The accommodation features a garden, a terrace and a swimming pool, providing a relaxing atmosphere for guests. Amenities include air conditioning, free Wi-Fi, parking, room service and a coffee shop.
10 3 reviews
Caledon
22/07 – 26/07
$515/nighttotal: $2060 (4 )
Spacious, Private Family Friendly 2 Bedroom Home
2 4
apartment , Caledon East
This Caledon East holiday home is situated 4.3km from The Old Pro Driving Range and within 9.7km of both Camden Dog Park and the Williams Mill Visual Arts Centre. This 232 square metre property offers two bedrooms, two bathrooms, sleeps four guests, and includes a fully equipped kitchen, laundry facilities, a fireplace, and a smart TV.
9.0 18 reviews
Caledon
22/07 – 26/07
$269/nighttotal: $1076 (4 )
Gorgeous Cozy Cottage Besides A Bustling Stream, Surrounded By Gorgeous Greenery
1 4
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.
Best Caledon lodging with parking
8.0 3 reviews
Caledon
22/07 – 26/07
$1162/nighttotal: $4648 (4 )
Modern Retreat With Loft & Spa-like Jacuzzi Tub
4 4
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.
9.0 25 reviews
Caledon
22/07 – 26/07
$203/nighttotal: $812 (4 )
Tosam Luxury Lodge Two Bedroom Suite
2 4
apartment , Toronto
This two-bedroom flat is located in Brampton, a suburb just west of Toronto, 30 kilometres from Canada's Wonderland and 37 kilometres from Casa Loma. The apartment has received excellent user ratings and very good ratings for location and cleanliness. The 93 square metre flat comfortably sleeps four guests. It offers a range of amenities, including free Wi-Fi, private parking, a fully equipped kitchen, outdoor dining space, and air conditioning.
8.0 9 reviews
Caledon
07/07 – 08/07
$150/nightfor 1 night
Suite A 2 Bedroom Apartment
2 2
apartment , Toronto
This Brampton apartment, situated approximately 16 kilometres from Toronto Pearson International Airport and 21 kilometres from Canada's Wonderland and Vaughan Mills Shopping Centre, offers convenient access to major attractions. Sleeping up to seven guests, this self-catering flat boasts a fully equipped kitchen, private parking, a terrace, and an outdoor fireplace, plus nearby amenities including a coffee shop and mini-market.
Caledon
07/07 – 08/07
$159/nightfor 1 night
Wmk Mcmillan Room
1 2
B&B , Erin
This guest house is located on the Credit River in Erin village, offering proximity to the Niagara Escarpment and Bruce Trail. This establishment provides two queen guest rooms accommodating up to two guests, featuring air conditioning, Wi-Fi, a swimming pool, and parking.