Whispering Pines Cottages - Vacation Rentals in Caledon Ski Club

Country Estate north of Brampton Ontario From US $2,273
         

New
House
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
Luxury 4BR Stay with Swim Spa, Golf and Fireplaces From US $892
         

Redstone Retreat- Cozy countryhouse w/3 bedrooms From US $356
         

New
House
  • Pet Friendly
  • Security/Safety
  • Fireplace/Heating
Cheltenham Suites From US $125
         

8.7 (164 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Cheltenham Suites From US $145
         

9.0 (120 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Beautiful nature themed house. (10 minutes from Orangeville downtown) From US $561
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Millcroft Inn & Spa From US $205
         

|
7.9 (169 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Peaceful Country House From US $213
         

10.0 (1 Review)
House
  • Parking
  • TV
  • Balcony/Terrace
Rustic cabin-inspired residence. From US $451
         

Charming Erin Country House near downtown From US $304
         

7.2 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury 4BR Stay with Swim Spa, Golf & Fireplaces From US $697
         

Redstone Retreat- Cozy countryhouse w/3 bedrooms From US $305
         

New
House
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens
Pro Tip: Whisperingpinescottages makes it easy to compare the best listings on Whisperingpinescottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Whisperingpinescottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Caledon Ski Club.

Weather in Caledon Ski Club

View the weather forecast for Caledon Ski Club before booking your Caledon Ski Club Vacation Rentals to confirm your best time to go.

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Caledon Ski Club Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Caledon Ski Club?
How many vacation rentals are available in Caledon Ski Club?

Currently, the total number of properties listed in 2026 is over 63 in the Caledon Ski Club area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Caledon Ski Club.