What is a booking window and why does it matter?
The best weeks go fast. Your window determines how early you can claim them at base price.
A booking window is the range of future dates within which your membership tier secures the standard base booking fee. Book within your window — you pay base price. Book outside it — you pay base price plus 30%.
Every date on the calendar is always available to book. Your window is not a lock on access. It's a lock on price.
Why it matters in practice
The most desirable Teaching Vacation weeks — peak summer dates, popular resort properties, holiday-adjacent weeks — get claimed months in advance. Members with longer windows book those weeks at base price well before shorter-window members or non-members even face the pricing decision.
By the time a non-member or short-window member tries to book a high-demand week, the choice is simple: pay the 30% premium or miss it.
Booking windows by tier
| Tier | Base-price window | A week booked 14 months out costs |
|---|---|---|
| No membership | None | Base + 30% |
| Travel — $95/year | ~13 months | Base + 30% |
| Medallion — $495/year | ~20 months | Base price |
| Enterprise — $1,495/year | ~24 months | Base price |
Reading the table: A Travel member trying to book a week 14 months out is just outside their window — they pay the 30% premium on that booking. A Medallion member booking the same week at the same time pays base price. Same week. Same resort. Different membership. $300 difference on a $1,000 booking.
The compounding effect
The window benefit compounds with every trip you take. A member who books three Teaching Vacations per year, each at $1,000 base fee:
| Scenario | Annual booking cost |
|---|---|
| No membership | $3,900 (3 × $1,300) |
| Travel — all within window | $3,000 (3 × $1,000) |
| Medallion — all within window | $2,850 (3 × $950 with 5% discount) |
The $495 Medallion membership costs less than the savings on two trips compared to booking without one.
How to use your window strategically
- Book as early as possible within your window for high-demand resorts and peak-season dates
- Set a reminder when new resorts launch — Medallion and Enterprise members are notified first, and first-wave weeks fill quickly
- Don't wait on dates you want — once a week fills, it's gone regardless of your membership tier