Find cottage rentals in Lake Simcoe / Orillia region. The Sunshine City, Orillia is located on the shores of Lake Couchiching and Lake Simcoe – part of the Trent-Severn Waterway – only half an hour from Toronto. This area features dozens of lakes, beautiful art galleries, golf courses, cycling trails and much more. Lake Simcoe is also well known for their fresh produce and variety of farmer’s markets which visitors can enjoy during their stay. There is also a 28km Rail-Trail from Oro-Medonte for any locomotive enthusiasts within the group!