Peak season (June – September): Hotels run 20–40% higher. Book 6 – 8 weeks out minimum. Pride Weekend in late June is the single busiest hotel weekend of the year – if that’s your trip, book 3–4 months out and expect prices to spike hard.
Shoulder season (April – May and October): My honest recommendation for most visitors. Genuinely pleasant weather, 15–25% cheaper hotels, thinner crowds. October in Toronto with the fall colour in High Park is one of the best things about living here.
Winter (November – March): Underrated and underpriced, and I will argue this until I’m gone. Hotel rates drop 25–40% off peak. The Distillery Christmas Market is genuinely world-class. Skating at Nathan Phillips Square is free and ridiculously fun. And the restaurant scene – arguably Toronto’s greatest strength, does not slow down one bit.