Jasper breaks down one of the trickiest parts of STR pricing that most operators never fully figure out: shoulder season. Low season and peak season have clear playbooks. Shoulder season is different. The weekday-weekend gap widens, occupancy swings from week to week, and the wrong settings in your pricing tool can quietly cost you revenue all the way through fall.


Freewyld currently manages over 4,000 properties across 75+ clients worldwide and $200 million in annual bookings. That data set informs every recommendation in this episode.


You will hear:

  • How to define your four seasons using occupancy thresholds: low (below 50%), shoulder (50-70%), high (70-90%), and peak (above 90%)
  • Why shoulder season is harder to price than both low and peak season, and what makes it behave differently from everything else on the calendar
  • How to read a future occupancy graph to identify exactly when your shoulder season starts and ends in your specific market
  • The weekday vs. weekend swing that defines shoulder season, and why a one-size-fits-all minimum stay strategy usually leaves money behind
  • How to set up custom seasonal profiles in PriceLabs: percentage vs. fixed pricing, minimum stay profiles by season, and check-in and checkout restrictions
  • Day-of-week price adjustments Jasper's team uses in shoulder season, including typical ranges for each day


We also talk about:

  • Why forcing longer minimum stays during shoulder season usually cuts demand without adding revenue, and what to do instead
  • How to download a PriceLabs seasonal profile as a CSV, edit it, and upload it across multiple units without starting from scratch
  • How Jasper's team used Claude to generate 20 seasonal profile CSVs for a client in a fraction of the time it would have taken manually


Mentioned in the Episode:


Favorite Takeaway:

"Be careful that you don't make your strategy too complicated. Only add complications if you're very confident it's going to increase your revenue. The challenge I see with some operators is they make it so complicated that their strategy becomes completely ununderstandable. You just don't know anymore why the prices are where they are."

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