The dimensional stability of thermally modified wood exposed to several wetting-drying cycles was analyzed. Specimens of dimensions 15×15 ×15 mm were thermally modified at 180 and 200 °C. The mass loss and chemical composition of the wood were determined in order to evaluate the effect and degree of modification. Afterwards, the radial, tangential, and volumetric swelling, anti-swelling efficiency, water absorption, water repellence efficiency, and mass loss due to wetting-drying cycles were determined and compared. The specimen's mass tended to decrease with each additional rewetting cycle. Additional extractives that were formed via thermal decomposition leached out during wetting cycles. Thermal modification positively affected the dimensional stability of all investigated species. The wood's swelling was reduced, a result attributed to hemicellulose degradation. Dimensional stability was improved by 24 to 30% following mild treatment and by 26 to 54% following more severe treatment. When specimens were exposed to six consecutive rewetting cycles, the swelling of the modified wood increased, whereas it slightly decreased for the control (hornification). The effective dimensional stability of thermally modified wood was reduced by 34 and 28.4% for beech, 47 and 19.6% for poplar, and 19.3 and 24.5% for spruce compared to the initial anti-swelling efficiency following the first wetting cycle.