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!
Escape to the gateway of cottage country without the long drive! Our Orillia & Lake Simcoe cottage rentals offer the perfect balance of lakeside tranquility and urban convenience, all just 90 minutes north of Toronto. Known as the “Sunshine City,” Orillia sits nestled between the glittering waters of Lake Couchiching and Lake Simcoe, providing an accessible paradise for families, boaters, and year-round adventurers. This region is renowned for its recreational diversity. In the summer, the Trent-Severn Waterway beckons boaters to explore its historic locks and scenic channels, while families love the shallow, sandy shores of Lake Simcoe for swimming and paddleboarding. Anglers can cast a line for perch and bass in world-class fishing spots, or enjoy ice fishing in the winter months on some of Ontario’s most popular hard-water destinations. Our rental portfolio in this area ranges from cozy waterfront cabins perfect for a quick weekend recharge to spacious family compounds near premier attractions. You’re never far from excitement here; spend a day hitting the slopes at nearby Mount St. Louis Moonstone or Horseshoe Resort, test your luck at Casino Rama, or explore the vibrant arts scene and festivals in downtown Orillia. Guests love the convenience of having major amenities close by—grocery stores, charming boutiques, and excellent dining are just minutes from your dock. Whether you are looking for a pet-friendly retreat with a fenced yard or a modern lake house with a private hot tub, our Orillia and Lake Simcoe rentals deliver an unforgettable vacation with less travel time and more play time. Browse our listings today and find your perfect “near north” escape.
Bdrms
Baths
Guests