Villas and Holiday homes in Caledon

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Caledon holiday homes
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196 Villa rentals in Caledon

Compare Holiday Homes with a Pool in Caledon

Having pool access at your city holiday home makes a proper swim in the heart of Caledon a delightful daily highlight.

The Trails Retreat (Private Cabin) - Caledon
9.9 342 reviews
Caledon
07/07 – 08/07
£187/nightfor 1 night

The Trails Retreat (Private Cabin)

1 2
cabin , Orangeville
This private cabin is situated near Orangeville, just a short distance from the Bruce Trail and Hockley Ski & Resort, offering a peaceful escape surrounded by nature. It has received excellent ratings for its location, cleanliness, and overall experience.
The studio comfortably accommodates up to four guests and features a kitchen with a fridge and microwave. Enjoy access to a shared swimming pool, a private garden, and a range of activities including yoga classes, chef-prepared meals, and discounts for longer stays.

Best family friendly Caledon villas and holiday home

Among the 196 accommodations in Caledon, here are the 3 best family friendly villas and holiday homes

84 M² House ∙ 2 Bedrooms ∙ 6 Guests - Caledon
9.0 1 review
Caledon
22/07 – 26/07
£89/nighttotal: £356 (4 )

84 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 4
house , Toronto
This private main-floor suite is located in a quiet Brampton neighbourhood, 4 minutes by car from the 410 highway and Centennial Mall, offering straightforward access to Toronto.
Spanning 83 square meters, this accommodation for up to six guests features two bedrooms, one bathroom, a fully equipped kitchen, air conditioning, a garden, and complimentary Netflix and Prime Video, with parking provided.
Gorgeous Cozy Cottage Besides A Bustling Stream, Surrounded By Gorgeous Greenery - Caledon
9.0 18 reviews
Caledon
22/07 – 26/07
£144/nighttotal: £576 (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.
The Grassy Oasis - Caledon
8.3 22 reviews
Caledon
07/07 – 08/07
£169/nightfor 1 night

The Grassy Oasis

1 2
house , Toronto
The Grassy Oasis villa is located in Brampton, a suburb of Toronto, just 6.6 km from the Mississauga Convention Center and 27 km from the Aviva Centre. This peaceful retreat offers a quiet escape from the city, with easy access to Toronto's attractions.
The villa is a one-bedroom property with one bathroom, covering 37 square meters and accommodating up to three guests. It features a fully equipped kitchen, a private garden, outdoor play equipment, free parking, and a private courtyard.

Frequently asked questions about villa rentals in Caledon

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Best Caledon villas and holiday homes with parking

Brick House On Broadway - Coach House - Caledon
9.6 16 reviews
Caledon
07/07 – 08/07
£121/nightfor 1 night

Brick House On Broadway - Coach House

1 2
house , Orangeville
This restored historic coach house, once part of Lester B. Pearson's grandparents' property, offers a private retreat in Orangeville, a short 500-meter walk from the town's historic core with its shops and restaurants, and is conveniently located for access to Hockley Valley, Mono Cliffs, and Island Lake hiking trails.
This one-bedroom, one-bathroom dwelling accommodates two guests and features a fully equipped kitchen with a fridge, freezer, and microwave, air conditioning, internet, and parking, with an outdoor side yard complete with a picnic table for enjoying the mature tree surroundings.
Lux Basement Apartment Getaway - Caledon
Caledon
22/07 – 26/07
£212/nighttotal: £848 (4 )

Lux Basement Apartment Getaway

1 4
house , Caledon East
This Brampton basement apartment offers convenient access to key locations, situated 16 kilometres from the Mississauga Convention Centre, 32 kilometres from Vaughan Mills, and within a 32 to 43 kilometre radius of attractions such as Canada's Wonderland and York University.
This property provides accommodation for up to four guests across 900 square metres, featuring a fully equipped kitchen with a microwave and toaster, air conditioning, free WiFi, and a washing machine, managed by a local host for a private getaway experience.
Perfect 10 Acres Private Quiet Property For Small Events & Family Gatherings - Caledon
10 1 review
Caledon
22/07 – 26/07
£876/nighttotal: £3504 (4 )

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

4 4
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.
Simple Plain Comfort - Caledon
9.7 59 reviews
Caledon
22/07 – 26/07
£259/nighttotal: £1036 (4 )

Simple Plain Comfort

3 4
house , Bolton
This Bolton house, sleeping six, is ideally located for exploring the town centre, with its proximity to Bolton's attractions needing further clarification to determine precise distances in kilometres.
The three-bedroom, two-bathroom property boasts a fully equipped kitchen, air conditioning, garden, parking, and is tastefully furnished for a comfortable stay, offering exclusive access for families or small groups.

Best Caledon villas and holiday homes with a garden

Private Off-grid Farm Retreat - Caledon
9.8 36 reviews
Caledon
07/07 – 08/07
£91/nightfor 1 night

Private Off-grid Farm Retreat

1 2
cabin , Guelph/Eramosa
This secluded off-grid cottage is situated 0.8km from the main farm buildings on a 50-acre farm in Guelph-Eramosa, within a 10–20 minute drive of Erin, Acton, and Guelph.
The 200 sq ft dwelling features a queen-size bed, living area, large windows, a deck, propane BBQ, fire pit, and sleeps two guests; nearby attractions include Belfountain Conservation Area, Rockwood Conservation Area, and Guelph Lake Conservation Area.
Cabin Stay And Play! 10 Mins To Canadian Open! - Caledon
9.8 521 reviews
Caledon
07/07 – 08/07
£289/nightfor 1 night

Cabin Stay And Play! 10 Mins To Canadian Open!

1 2
cabin , Erin
This Erin, Ontario lodge is located 2km from the town centre and 0.35km from Caledon Golf Course, offering seclusion yet easy access to local amenities.
Sleeping four guests, this self-catering retreat boasts two bedrooms, one bathroom, a jacuzzi, and on-site amenities including a BBQ, patio, pool table, and Golden Tee arcade game, alongside access to acres of walking trails.
Character-filled Farm Guest House On 8 Acres - Caledon
9.9 75 reviews
Caledon
25/08 – 27/08
£121/nighttotal: £242 (2 )

Character-filled Farm Guest House On 8 Acres

1 2
gîte , Adjala-Tosorontio
This charming gîte is located in Adjala-Tosorontio, 45km north of Toronto, close to Tottenham and Palgrave, and 20km from Orangeville or Alliston. It has consistently received excellent ratings for its location, cleanliness, and user experience.
The gîte is a 2-bedroom, 1-bathroom property that can accommodate up to 4 guests. It features a spacious living area, a fully equipped kitchen, and a private garden, as well as access to a working hobby farm with a variety of animals. Guests can enjoy hiking trails on the surrounding 400 acres of conservation land, or visit nearby attractions like Hockley Valley Resort and Adamo Winery.
The Green Lodge - Upper Level Raised Bungalow - Caledon
10 1 review
Caledon
22/07 – 26/07
£145/nighttotal: £580 (4 )

The Green Lodge - Upper Level Raised Bungalow

1 4
bungalow , Orangeville
This detached house is located in Orangeville's North quarter, a short walk to the Lake Conservation Area and a brief drive to the Fork of the Credit and Hockley Valley parks and trails, with Blue Mountain and Toronto approximately 160 kilometres away.
This detached house offers luxury boho style open-concept living for up to four guests, featuring two queen-sized bedrooms, a full bathroom, a well-equipped kitchen with modern appliances, and a 20.9 square metre rear deck overlooking the garden.
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