Find short term rentals in Caledon at the best prices

1403 available short term rental offers

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Caledon short term rentals
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Best Short term and Weekly rentals in Caledon

Best Caledon luxury short term rentals

Caledon Country Apt Near Golf, Venues & Horses - Caledon
9.7 55 reviews

Caledon Country Apt Near Golf, Venues & Horses

apartment, Caledon
This apartment is located on the Niagara Escarpment in Caledon, offering scenic views and easy access to the Bruce Trail, just a short drive from the charming town of Caledon Village. It has received excellent ratings for its location, cleanliness, and overall experience.
The self-catering accommodation is a spacious three-bedroom suite with one bathroom, suitable for up to six guests. Amenities include a well-equipped kitchen, a private entrance, a garden, a heated pool (for an extra fee), and a range of outdoor activities, including hiking, cycling, and bonfires.

Best Caledon Short term rentals with a jacuzzi

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

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.
Caledon Trailside Retreat-sleeps 6 - Caledon
10 5 reviews

Caledon Trailside Retreat-sleeps 6

apartment, Caledon
This spacious country home in Caledon is located just 5 kilometres from TPC Toronto at Osprey Valley, ideal for those attending the RBC Canadian Open.
Offering accommodation for up to six guests across three bedrooms, this property features two bathrooms, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, a family room, and a deck with a BBQ, all set on 1.5 acres of land.
The Hockley Hill House -4 Br W/escarpment Views - Caledon
No reviews

The Hockley Hill House -4 Br W/escarpment Views

apartment, Orangeville
This modern country house is situated high in the hills of Hockley Valley, part of the Niagara Escarpment, adjacent to farmland and a UNESCO World Conservation site, offering picturesque views and seclusion within 16 kilometers of Orangeville.
This 4-bedroom, 3-bathroom residence accommodates up to 8 guests and features a heated outdoor swimming pool (seasonal), a year-round hot tub, wood-burning fireplaces, and a 4-stall barn for horse boarding, with direct access to the Bruce Trail for hiking and mountain biking.
Luxury 4br Stay With Swim Spa, Golf & Fireplaces - Caledon
8.0 1 review

Luxury 4br Stay With Swim Spa, Golf & Fireplaces

apartment, Caledon East
This Caledon East residence is located near rolling hills, scenic trails and conservation areas, a short drive from local markets, cafés, and family-owned restaurants, as well as golf courses and equestrian centres.
This four-bedroom, three-bathroom flat accommodates up to eight guests and offers a private golf simulator, a swim spa, a double-sided fireplace, a dedicated workspace, two projectors, a full gym, and parking for over six vehicles.

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

Spacious Cozy 4br Orangeville Home W/deck! 10-minute Walk To Headwaters Hospital - Caledon
No reviews

Spacious Cozy 4br Orangeville Home W/deck! 10-minute Walk To Headwaters Hospital

apartment, Orangeville
This family-friendly apartment in Orangeville is conveniently situated 240 metres from Island Lake Conservation Area and Theatre Orangeville, with Hockley Valley Resort and Heathlands Links at Osprey Valley also close by.
This spacious 276 sqm residence offers four bedrooms, two and a half bathrooms, a living area with a fireplace, a fully equipped kitchen, in-unit laundry, a private terrace, a garden, and barbecue facilities, complemented by free Wi-Fi and air conditioning.
Luxe Cinema Suite | Guest Favourite | 25m To Yyz - Caledon
9.9 64 reviews

Luxe Cinema Suite | Guest Favourite | 25m To Yyz

B&B, Toronto
This luxurious basement suite enjoys a prime location near Highway 410, providing easy access to Pearson International Airport (approximately 40km) and Toronto city centre (approximately 80km), with a grocery store within walking distance.
The self-contained apartment, sleeping up to three guests, features a fully equipped kitchen, 70" TV with streaming services, a queen-size bed, a pull-out sofa bed, and a modern bathroom with a shower and bidet; complimentary toiletries are provided.
Cozy And Private Basement Apartment / Ideal For Relaxation Or Work - Caledon
8.6 4 reviews

Cozy And Private Basement Apartment / Ideal For Relaxation Or Work

apartment, Toronto
This Brampton apartment, a 16km drive from Toronto and a 24km drive from Toronto Pearson International Airport, provides easy access to Canada's Wonderland and Woodbine Racetrack.
The two-bedroom, one-bathroom property sleeps six guests and features a well-equipped kitchen, high-speed Wi-Fi, air conditioning, and pet-friendly accommodation.
Bright, Stylish Basement Apartment - Caledon
9.7 95 reviews

Bright, Stylish Basement Apartment

apartment, Toronto
This basement flat is situated in a peaceful residential area in Brampton, just a short drive (around 5km) from Trinity Common Mall, Bramalea City Centre, and Brampton Civic Hospital. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The self-catering flat offers a private bedroom with a queen-size bed and a comfortable living area with a pull-out sofa bed, accommodating up to six guests. It comes equipped with a kitchen, laundry facilities, and complimentary amenities such as coffee, tea, and toiletries, ensuring a comfortable stay.

Best Caledon lodging with parking

Hockley Valley Cozy Cottage With Waterfront Access - Caledon
10 2 reviews

Hockley Valley Cozy Cottage With Waterfront Access

apartment, Orangeville
This two-bedroom flat is located in Mono, 3 kilometres from Orangeville, and backs onto the Nottawasaga River, offering a countryside escape with proximity to Mono Cliffs Provincial Park.
This apartment sleeps up to four guests and features internet, air conditioning, and a kitchen, with year-round activities available including hiking and visiting local wineries and cideries.
Elegant Two Bdr Apartment With Private Entrance - Caledon
9.6 50 reviews

Elegant Two Bdr Apartment With Private Entrance

apartment, Toronto
This two-bedroom basement flat is situated in the Fletcher Meadow area of Brampton, a suburb of Toronto, approximately 30km from downtown Toronto.
The self-contained apartment sleeps four guests, offering a workspace, free driveway parking, and a fully equipped kitchen including a dishwasher; additional heating is provided.
Hockley Valley Cozy Cottage With Waterfront Access! - Caledon
10 3 reviews

Hockley Valley Cozy Cottage With Waterfront Access!

apartment, Orangeville
This two-bedroom flat in Mono offers private waterfront access to a river, located approximately 6.1 kilometres from Orangeville's amenities and cultural attractions, including Theatre Orangeville and the Dufferin County Museum & Archives.
This property accommodates up to four guests and features a fireplace, outdoor gazebo, and is conveniently situated near outdoor recreation at Hockley Valley Resort and Mono Cliffs Provincial Park.
The Perfect Getaway - Caledon
8.0 6 reviews

The Perfect Getaway

apartment, Orangeville
This Orangeville apartment, an 11-minute walk from the Orangeville Theatre and a 1.8km drive from Island Lake Conservation Area, offers convenient access to local attractions. This two-bedroom, one-bathroom property sleeps six guests and includes Wi-Fi, a fully equipped kitchen with oven, stovetop, and microwave, in-unit laundry, air conditioning, parking, and a fireplace.
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