Shoulder season is where most rentals lose money. The fix is rarely a bigger discount — it's reminding the right people that you exist.
Email one: the memory
A photo from their stay and a single line. No offer yet. It reopens the relationship.
Email two: the reason
Something specific happening locally in the quiet months — a festival, a season, a walk. Give them a reason to come now.
Email three: the offer
A returning-guest rate for selected dates, with a clear deadline. This is where the bookings land.