General flight/hotel question

Question

For booking airfare and hotels - how far in advance should I book?

A little background..... at my place of employment, all employees are asked each December to submit their vacation requests for the following year. We cannot choose anything before this time, and we have to wait until our request is either accepted or rejected (my work team goes by seniority and I am low man on the totem pole).

I won't be able to book anything until at least mid to late December, once the following year's vacation date has been established. I know the best time to visit is either April/May or September/October.

Answer

Booking airfare and hotels for Hawaii can be tricky if you have to wait until mid to late December to confirm your vacation dates. Here’s a detailed breakdown of what to consider:

For airfare:

Domestic flights to Hawaii are generally best booked 4-6 months in advance for the best fares, though you can still find reasonable prices 2-3 months out if you monitor deals.
Since you’ll be booking in December for April/May or September/October, you are within a workable window. Start checking flights as soon as your dates are confirmed.
Use fare alert tools like Google Flights, Hopper, or Skyscanner to monitor trends and get notified of price drops immediately after your dates are confirmed.
Keep in mind that weekends and holidays, especially spring break and Christmas/New Year, see higher prices, so being flexible with departure days can save money.

For hotels:

Hawaii hotels, especially on popular islands like Oahu and Maui, book quickly. For April/May or September/October, 3-6 months ahead is usually fine.
Luxury resorts and highly rated vacation rentals often fill up fast, so if you have specific preferences, prioritize booking as soon as your dates are confirmed.
If you miss the early window, consider alternative accommodations like smaller boutique hotels, condos, or Airbnb listings—sometimes you can find last-minute deals, though selection may be limited.

Additional tips:

Be ready to book immediately once your vacation dates are confirmed, as delays could mean higher prices or less desirable accommodations.
Check cancellation policies—flexible booking options give peace of mind in case your vacation request is delayed or adjusted.
Sign up for loyalty programs or travel booking sites to access member rates or promotions that may help offset costs.

Overall, given your work constraints, mid to late December is not too late to book for a spring or fall Hawaii trip. Staying vigilant and acting quickly when your dates are approved will give you the best chance to secure flights and accommodations at reasonable rates.