Pricing for the end of September

Question

I decided to go to Maui at the end of September, because based on my research it is " shoulder season" and prices are cheaper. I knew it was the hottest month and tends to be more windy- but I was willing to tolerate that stuff for a less expensive vacation. I also checked before booking my airfare, that there was nothing major going on to have more tourists.

I have spent a nauseating amount of hours looking at every site out there for accommodations. What I am finding upsetting is that I find the end of September and October are expensive compared to July, August, the beginning of September and November. Can anyone explain the prices differences, and can I expect rates for my dates- September 24- October 1 to go down ?

Answer

Aloha,

Pricing for Maui accommodations at the end of September can sometimes be surprisingly high despite it being considered “shoulder season.” There are a few reasons for this:

School schedules and fall travel: Late September to early October can coincide with certain school breaks (especially private schools or local Hawaii schools), so some families take advantage of the period before the big holiday season, increasing demand.
Event-driven demand: Maui often hosts conferences, weddings, or local events in this timeframe, which can drive up hotel prices even if overall tourist numbers are slightly lower.
Limited inventory for certain hotels: Popular resorts may have fewer discounted rooms available at this time, especially if they are popular with honeymooners, families, or conference attendees.
Weather considerations: While it is hotter and occasionally windy, many visitors prefer the slightly more predictable sunny mornings in September, especially for snorkeling and beach activities, which can maintain demand for certain properties.

As for whether rates will go down for your dates (September 24–October 1):

Hotels often offer limited last-minute discounts, but for popular or highly-rated properties, rates may remain stable or even increase as availability shrinks.
If your travel dates are flexible, checking nearby weeks can sometimes yield lower prices, but the end of September is already a sought-after window for many travelers seeking good weather before the rainy season starts in October/November.
Consider booking directly with hotels or reputable vacation rental platforms, as they sometimes offer last-minute deals or free upgrades that aren’t reflected on larger booking sites.

In summary, while September is generally shoulder season, specific demand factors for your exact dates can keep prices higher than expected. Waiting for rates to drop may work for some mid-tier hotels or vacation rentals, but for top resorts, it’s safer to book soon to secure your preferred property.

Pricing for the end of September

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