The months of January and early February (peak winter) are the least crowded times for visiting Disney World. Additionally, early September through mid-November (back-to-school season) is also the best time when Disney World gets fewer crowds. Do remember that weekends, summer vacation, school breaks and holiday periods are the busiest times of year to visit Disney World. You will be able to stay at the cheapest resorts and save big when visiting Disney World during off-season.