Six regions for a winter cottage or ski chalet, with what to do in each and drive times from Toronto and Ottawa.
An Ontario cottage in winter is a different trip from the summer one: frozen lakes instead of docks, a wood stove instead of a campfire, and ski hills, skating trails and snowshoe paths within a short drive. Weeks are often easier to find and cheaper than in July, except at Christmas and March Break.
Not every cottage is built for the cold, so look for winter-ready places with year-round road access and proper heating. Here are six regions where winter is part of the season, ordered by the kind of trip they suit best.
Ontario’s biggest ski resort, Blue Mountain, sits above Georgian Bay with a pedestrian village at its base, and the ski season runs from about December to March. Large chalets around Collingwood and Craigleith suit several families together. After a ski day, the outdoor Nordic baths of Scandinave Spa are a few minutes away.
Best for: downhill skiing, groups, a spa day
About an hour from Toronto, Lake Simcoe becomes one of the busiest ice-fishing lakes in North America from January to March. Just off Highway 400 in Oro-Medonte, Horseshoe Resort and Mount St. Louis Moonstone offer skiing for beginners to experts, and Horseshoe also grooms cross-country trails on the edge of the Copeland Forest, a good place for snowshoeing.
Best for: a short weekend, ice fishing, first-time skiers
Muskoka’s lakes freeze into a quiet white landscape. The best-known winter outing is the ice-skating trail through the forest at Arrowhead Provincial Park near Huntsville, and there is skiing and snowshoeing close to town. A Muskoka cottage in winter means long evenings by the fire and walks on snowy lake roads.
Best for: skating, cozy weekends, couples
Haliburton has many cottages built for year-round use, and winter is a real season here: skiing and snowboarding at Sir Sam’s above Eagle Lake, long snowmobile trails between the lakes, and dog sledding. Minden and Haliburton village are the main stops, about 2½ to 3 hours from Toronto.
Best for: snowmobiling, dog sledding, family skiing
Highway 60 through Algonquin is ploughed all winter. Ski the Fen Lake trail at the West Gate or the longer Leaf Lake trail network, snowshoe almost anywhere off the ski trails, and listen for wolves in the silence. Cottages near the park in Dwight, Oxtongue Lake and Whitney make a warm base; a park permit is needed for each day in the park.
Best for: cross-country skiing, snowshoeing, wildlife
Calabogie Peaks, about an hour west of Ottawa, has one of the biggest vertical drops of any ski hill in Ontario, with views over Calabogie Lake from the top. Cottages on the surrounding lakes make an easy winter weekend from the capital without the long drive north.
Best for: skiing near Ottawa, a quiet lake weekend
Every cottage on our site is rented directly from its owner, with no booking fees. Use the “winter” filter in search to find winter-ready cottages, or open a region above to read the full guide and write to the owner about your dates.
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Updated 2026-10-19
