What is the Best Day to Book a Resort?

Accommodations are one of the biggest travel expenses, so it's never a bad idea to try and maximize your savings. Airfare, hotel and resort prices are dynamic, fluctuating based on supply and demand, so the price you see searching one day might change the next, even if the dates and location of your trip remain the same. Trying to lock in a cheaper reservation on a specific day or time of day is unfortunately mostly a myth, so when is the best time to book?


Contrary to popular belief, there isn't a single "best day" applicable to resort or hotel booking. Here are three common myths to dispel: booking on weekdays (Monday-Tuesday) is always cheaper, weekends are the worst time to book a resort, and booking last-minute guarantees the best deals. There are several factors that influence pricing and availability, making a "one-size-fits-all" approach impractical. Fortunately, there are some strategies you can use to find lower rates, most of which boil down to timing.

The world is a big place, and the most affordable rates depend on when and where you’re planning to go. Resort and room rates vary based on factors like how far in advance you’re making reservations, what time of year you’re traveling, and whether or not there’s high demand for that destination. Instead of focusing on a specific day, consider these key factors to strategize your resort booking:

  • Seasonality: Peak seasons (holidays, school breaks, etc) typically command higher prices. Conversely, shoulder or “off” seasons usually offer better deals.
  • Demand and Trends: By researching booking trends for your desired resort and destination, you can analyze past pricing fluctuations and identify potential discount periods.
  • Promotions: Many resorts offer special promotions and flash sales throughout the year, especially during off season. 
  • Flexibility: If possible, maintain flexible travel dates. Having some wiggle room allows you to capitalize on sudden price drops or last-minute deals.
  • Loyalty Programs: Some resorts offer loyalty programs that can unlock exclusive discounts and early booking opportunities.

Now that you understand the time of day or day of the week doesn’t matter much when it comes to booking, you can focus on the bigger picture. It is always off-season somewhere, as the Northern and Southern Hemispheres are opposite; spring in one hemisphere means fall in the other. Additionally, the rainy season is normally the off-season and therefore cheaper. For example, the rainy season in Hawaii is from mid-November to early March, so booking a resort during that time will result in a different rate than taking a trip during peak season. 


The allure of a luxurious resort beckons, with sparkling pools, pristine beaches and endless relaxation and pampering in store, but navigating the booking process can be overwhelming and feel like deciphering a secret code. Before you dive into the booking frenzy, identify your priorities, and consider factors like: your budget, flexible travel dates and travel style. Here are a few tips to transform your resort booking from a stressful experience into a smooth and successful endeavor.

Research is key to finding the perfect resort and securing the best deal. Utilize online resources including resort websites to check for promotions, packages and loyalty program benefits, and travel booking platforms where you can compare prices and read guest reviews. Subscribe to the resort's mailing list to receive notifications about flash sales and special offers. Reading travel review websites and blogs can give you valuable insights from other travelers' experiences, and help you discover hidden gems and insider tips for your chosen destination.

When possible, leverage the power of flexibility. Opting for shoulder seasons or less popular travel times or locations can yield significant savings. Also explore creative solutions like flying into smaller airports near your destination, which might offer cheaper flights for example. Lastly, don’t be afraid to negotiate. Depending on the resort and occupancy, attempting to negotiate the rate, especially during off-peak seasons, might yield positive results.

Booking a resort isn’t an exact science, but by doing your research and having some flexibility, you can transform your booking experience from a daunting task into a rewarding journey, paving the way for an unforgettable vacation. Looking for a hassle-free booking experience? We can help. Call us at 888.598.6353 or email reservations@eastwest.com for help planning your next trip.