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When is the Best Time to Book a Resort Vacation? Solved!

By: Swena Kalra

Edited By: Scott Sidders

Updated on November 6, 2023

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You're not alone if you're dreaming of a sunny beach getaway. Resort vacations are trendy and for a good reason. Nothing beats soaking up the sun, swimming in the ocean, and enjoying all the activities and amenities that resort towns offer. But a resort vacation can be expensive, so you'll want to plan ahead and book at the right time to get the best deals.

When is the best time to book, you ask? That all depends on a few factors. You'll want to consider the weather, school holidays, and special events when deciding when to book your resort vacation. Keep reading to learn more about how to choose the best time to book your next resort vacation.


Here are a few things to keep in mind when trying to decide when is the best time to book a resort vacation:

1. The Time of Year You Want to Travel

Cancun resort during a sunset

One of the most critical factors in deciding when to book your resort vacation is the time of year you want to travel. Resort towns are busiest—and most expensive—during peak season, which generally runs from April to June and September to November in North America and Europe and from late June to August in destinations like Mexico.

If you're hoping to snag a great deal, travel during the shoulder season instead. Shoulder season is the period just before or after peak season when tourism starts to pick up but hasn't quite reached its peak yet. For example, in Florida, the shoulder season runs from April through May and again from September through November. Not only will resorts be less crowded during shoulder season, but you'll also find better accommodations, activities, and airfare deals. It's a win-win!

2. Consider Local Events and Holidays

Christmas Tree on Quinta Avenida, famous shopping street in Playa Del Carmen, Mexico

When deciding the best time to book your resort vacation, it's essential to consider local events and holidays. Many towns host festivals and events that attract large crowds and increase lodging prices. If you're looking to avoid crowds, research the town's events calendar before booking your trip. The same goes for holidays.

Many people travel during holidays like Christmas, New Year's, and Easter, so you can expect resorts to be more expensive and crowded. If you're looking for a deal, consider traveling before or after a holiday. You'll avoid the crowds but still be able to take advantage of festive decor and holiday-themed activities. This is especially true for Christmas and New Year's—traveling during the week between Christmas and New Year's Day can be much cheaper than traveling during either holiday.

3. Your Destination's Weather Patterns

Palm trees on the seashore in windy weather.

Another factor to consider when booking your resort vacation is your destination's weather patterns. After all, there's no point in paying top dollar for a beachfront villa if it's going to rain the entire time you're there! In general, it's best to avoid booking a resort vacation during hurricane season (June 1 – November 30) since tropical storms can disrupt travel plans before and after landfall. If you're set on traveling during hurricane season, however, opt for a destination like Hawaii which rarely sees hurricanes.

In addition to avoiding hurricane season altogether, pay attention to the average rainfall in your destination of choice. For example, Cancun experiences heavy rains from May to October—meaning those months are usually off-limits for travelers hoping to spend their days lounging by the pool or soaking up the sun on the beach. It's also important to check the forecast before you book. If a hurricane is predicted to hit your destination of choice in the next few weeks, it's best to wait until after the storm has passed to make your reservation. You don't want to risk being stranded at the airport or stuck in a hotel room with no power!

4. Your Budget

Piggy bank resting on the tropical beach.

Of course, your budget is one of the most critical factors in deciding when to book your resort vacation. As mentioned earlier, resort towns are typically much more expensive during peak season than shoulder season or low season (the period between hurricane season and shoulder season). So, if saving money is a priority, aim for dates outside peak season.

You'll still be able to enjoy all of the activities and amenities that resorts offer without having to shell out as much cash. Another way to save money on your resort vacation is by booking an all-inclusive package instead of purchasing accommodations, meals, and activities separately. All-inclusive packages often cost less per day than pay-as-you-go plans—plus, they offer added peace of mind knowing that everything is taken care of upfront. It's one less thing to worry about while you're on vacation!

5. Your Schedule

Tourist looking at arrivals and departures table

Last but not least, consider your schedule when deciding when to book your resort vacation. Aim for dates outside peak or shoulder season if you have a flexible work schedule. Not only will you save money, but you'll also avoid crowds and enjoy better weather. However, if you can only travel during certain times of the year, don't worry—there are still ways to save. For example, many resorts offer discounts for booking early or late in the season.

So, if you're planning a winter getaway, look for resorts that offer early bird specials for reservations made months in advance. Alternatively, if you're looking to travel last-minute, keep an eye out for last-minute deals that can often be found just a week or two before your desired travel dates. We had a great experience at a resort in Cozumel, the place had so many fun things to do!

Overall, there is no definitive answer as to when is the best time to book a resort vacation—it depends on personal preferences and priorities. Aim for dates outside of peak season if you're looking for ways to save money on your trip without sacrificing quality or experience. And if you're set on traveling during peak season, try to book your trip early or late in the season to take advantage of early bird specials and last-minute deals.

When you decide to travel, remember to check the weather forecast in advance and purchase travel insurance to protect yourself in any unforeseen circumstances. You want your resort vacation to be as seamless and stress-free as possible!

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