The Best Time to Plan Your Winter Vacation

The weather is beginning to get warmer, which means vacation season is just around the corner. However, we have an argument to make with summer holiday trips. Sure, it’s a great chance to get out and explore new places, but odds are, your base town or city is already having stellar weather. Why would you get out of town just as you gain the ability to walk around in shorts and flip flops? This, we posit, is why you should save your vacation days and rainy-day fund for a winter vacation.

Unfortunately, planning a winter vacation can be difficult; the season is split into several high-demand periods with low-demand weeks scattered throughout. Hotels, flights, and other types of reservations are on separate schedules, and it can be difficult to schedule each portion of your trip at the time when it is most affordable to purchase. Don’t worry—we’re here to help.

Most travel sites recommend booking hotels far in advance—at least one month prior to your arrival. This allows for room availability and the ability to avoid last-minute price increases for popular destinations. If, however, you want to stay somewhere like Chateau Laurier, you should book your room as soon as you finish reading this article. We’re only partially kidding; famous and historic hotels often raise prices significantly around holidays, events, and certain seasons. In Ontario, that can mean anything from Christmas to ski season.

If you are planning to visit in the winter but want to stay at an Air BnB or similar space, you best option is to book as far in advance as possible. Individual renters create and provide their own rates, meaning you are unlikely to see price hikes as the vacation draws closer. You will, however, see a decrease in availability. To guarantee a spot, it is best to plan and book your reservation as soon as you settle on a date and location.

If you’re planning to fly here, you might want to hold off on purchasing plane tickets. Business Insider reports that the best time to book flights for your winter vacation, excluding the holidays, is 62 days in advance. If you want to visit us in February, start looking for flights in December. However, if you plan to visit Ontario for a Winter holiday (did somebody say Winterlude?) the same report advises purchasing flights 11 weeks in advance, putting you at the end of October. Of course, it is always good to keep dates flexible when booking flights, but if you strategically plan, you can save a lot of money with a well-booked plane ticket.