There are no timeshares in the Barrie / Orillia area any longer. The Carriage Ridge and Carriage Hills properties closed and were sold years ago. The new owner sold some units as condos and others he rents out as vacation rentals. In the Collingwood area I see mainly studios for the next couple of months at a very few resorts (ie; Club Cranberry) for over $700. Cndn/week. You likely wont find anything between this May & Sept at this point in time. A couple of months ago I was able to book at week at Calabogie Lodge (closer to Ottawa) for May but only on an exchange, there were no Extra or Last Call weeks available. We live 20 mins from Barrie and Orillia and about 1hr from Collingwood so I am very familiar with the area.
~Diane