Inspired by natural creatures, superhydrophobic surfaces with various adhesion behaviors have attracted significant scientific interest. In this study, by controlling the laser fluence, the scanning times, and the subsequent cleaning method, microcolumn arrays with different morphologies were fabricated on 304 stainless-steel surfaces using picosecond laser direct writing. To achieve wettability transition, the laser-processed samples were then subjected to heat treatments (120 °C) in air and in a low vacuum environment (6 kPa). The results show that after heat treatment in different environments and with various time lengths, the laser-processed surfaces become hydrophobic surfaces with different adhesion properties. It is worth noting that while surfaces heat-treated in air exhibit weak wettability transition potential and high adhesion, the surfaces heat-treated in a low vacuum environment present superhydrophobic and low adhesion properties with a minimum sliding angle of about 3.14°. Moreover, the low-vacuum heat-treated surfaces retain good superhydrophobic properties after 1 month of observation as well as an abrasion test. These transitions in hydrophobic behavior and adhesion properties may be mainly attributed to the heat treatment-induced (in the air or in a low vacuum environment) redistribution of surface compounds and the microstructure-induced alternation of the solid-liquid contact state. By controlling the laser processing parameters and the heat treatment time and environment, stable wettability transition and flexible adhesion control of stainless steel can be easily achieved.