Vacation Rentals in Caledon

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Caledon holiday rentals
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1633 Holiday rentals and Airbnb in Caledon

Superior Family-Friendly Holiday Rentals in Caledon

Compare family holiday rentals in Caledon with space and amenities for all.

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.
Lakeview Private Suite With Kitchen (Twin Or King) - Caledon
8.6 7 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.
3 Separate Sleeping Rooms On 23-acre Horse Farm - Caledon
10 49 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.
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 Caledon holiday rentals with parking

Resort Style Entire Guesthouse (2 Rooms, Kitchen) - Caledon
9.2 258 reviews

Resort Style Entire Guesthouse (2 Rooms, Kitchen)

house, Adjala-Tosorontio
This private suite is situated on conservation land just minutes from the Equestrian Park, Bruce Trail, Hockley Valley Resort, and Woodington Lake Golf, offering a peaceful retreat in the heart of Adjala-Tosorontio. The accommodation has consistently received excellent ratings for its location, cleanliness, and overall experience.
The self-contained suite features a bedroom, living room, and private bathroom, providing ample space for a comfortable stay. Guests can enjoy a fully equipped kitchen, access to a private outdoor dining area, fire pit, charcoal grill, and a spacious garden, as well as the opportunity to relax in a Jacuzzi.
Spacious Cozy 4br Home W/patio Decknear Hospital! - Caledon
9.0 6 reviews

Spacious Cozy 4br Home W/patio Decknear Hospital!

apartment, Orangeville
This four-bedroom house in Orangeville is situated 800 metres from Headwaters Health Care Centre and 8 kilometres from Mount Alverno Luxury Resorts, offering convenient access to local amenities and attractions including Island Lake Conservation Area and Broadway boutiques.
This spacious property, ideal for families and groups of up to ten, features air conditioning, a jacuzzi, a garden, a fitness centre, parking, a fully equipped kitchen, a patio with a BBQ, and complimentary Wi-Fi.
Luxury Estate In Caledon On! - Caledon
9.1 36 reviews

Luxury Estate In Caledon On!

apartment, Caledon
This spacious house is located in Caledon, just a short drive from the historic Caledon Village and its shops and restaurants.
The property sleeps up to 16 guests and features 3 bedrooms, 3 bathrooms, a fully equipped kitchen with a dishwasher and microwave, air conditioning, and free parking.
Charming Log Home - 25 Private Acres In Caledon - Caledon
10 71 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.

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Holiday Rentals with a Balcony in Caledon

Browse holiday rentals with balconies in Caledon and enjoy sweeping city views from your own space.

Mono Countryside Apartments - Caledon
No reviews

Mono Countryside Apartments

apartment, Orangeville
This Orangeville flat is located in Mono, 4 minutes by car from Hockley Valley Resort and 2 minutes by car from Sharon Lake, offering convenient access to local attractions such as Heathlands at Osprey Valley and Island Lake Conservation Area.
This one-bedroom, one-bathroom apartment accommodates two guests and includes a full kitchen, air conditioning, Wi-Fi, on-site parking, and a private terrace, with a garden and outdoor furniture also available.
Charming Log Home - 25 Private Acres In Caledon - Caledon
10 3 reviews

Charming Log Home - 25 Private Acres In Caledon

apartment, Caledon East
This family-friendly apartment in Caledon East is located 45 kilometres from the Greater Toronto Area and close to the Albion Hills Conservation Area.
This 204 square metre holiday home offers 3 bedrooms and 2 bathrooms for up to 8 guests, featuring a kitchen with a fridge and microwave, a terrace, garden, spa, parking, and on-site walking trails.
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.
Hockley Valley Resort - Caledon
8.1 1054 reviews

Hockley Valley Resort

resort, Orangeville
Hockley Valley Resort in Orangeville offers a family-friendly escape, located under 15 minutes by car from Orangeville and the Hockley Valley Provincial Nature Reserve, with Luther Marsh Conservation area approximately 100 kilometres away.
This establishment boasts an 8,000 sq ft spa, indoor and outdoor swimming pools, an 18-hole golf course, a ski hill with 16 runs, and on-site dining at the farm-to-table restaurant, Cabin, and the lobby bar, Babbo, with Adamo Estate Winery just 1 kilometre down the road.

Best Caledon holiday rentals with air conditioning

Escape To A World Of Comfort And Elegance. - Caledon
9.3 9 reviews

Escape To A World Of Comfort And Elegance.

apartment, Caledon East
This five-bedroom, three-bathroom property is a tranquil apartment located in a ravine with a private pond, offering a serene natural escape within Caledon East.
This spacious accommodation comfortably sleeps ten guests and features a gourmet kitchen, integrated sound system, and a luxurious steam shower, perfect for family reunions and group getaways.
Lakeside Private Suite (Queen Bed Room) - Caledon
8.0 3 reviews

Lakeside Private Suite (Queen Bed Room)

house, Adjala-Tosorontio
This self-catering villa in Adjala-Tosorontio is ideally situated for exploring the region, with Albion Hills Nature Reserve just 13 kilometres away, Island Lake Conservation Area 27 kilometres away, and Caledon Equestrian Park a mere 10 kilometres distant.
This property offers accommodation for up to two guests, providing complimentary Wi-Fi and air conditioning, along with essential amenities such as towels, linens, and toiletries, ensuring a comfortable stay for those visiting local attractions like the Orangeville Theatre and the Alton Mill Arts Centre.
30 Minutes Drive To Pearson Airport - Caledon
8.9 196 reviews

30 Minutes Drive To Pearson Airport

apartment, Caledon
This apartment is located in Caledon, just a short drive from major stores and restaurants, offering easy access to both the town's amenities and the surrounding natural beauty. It has received very good ratings for location, cleanliness, and overall experience.
This self-catering dwelling offers a comfortable space for up to two guests, with one bedroom and one bathroom. It comes equipped with amenities such as air conditioning, internet access, and parking, as well as the added benefit of being pet-friendly.
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.

Uncover Exclusive Holiday Rentals in Caledon

Treat yourself to smart-home features, high-end interiors, and curated artwork at luxury holiday rentals in Caledon.

Casa Caledon-secluded Suite Surrounded By Nature - Caledon
10 155 reviews

Casa Caledon-secluded Suite Surrounded By Nature

house, Caledon

Downtown Holiday Rentals in Caledon

Spend less time navigating public transport and more time exploring attractions from central holiday rentals in Caledon.

Bunkie In The Forest - Caledon
9.7 157 reviews

Bunkie In The Forest

cabin, Caledon East
Studio Apartment - Caledon
9.7 260 reviews

Studio Apartment

studio, Caledon East
Escape To A World Of Comfort And Elegance. - Caledon
9.3 9 reviews

Escape To A World Of Comfort And Elegance.

apartment, Caledon East
Charming Log Home - 25 Private Acres In Caledon - Caledon
10 3 reviews

Charming Log Home - 25 Private Acres In Caledon

apartment, Caledon East
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