Resveratrol (RSV) is a bioactive phytoconstituent that has potential applications in respiratory diseases. However, poor oral bioavailability is the major hurdle to its clinical use. In the present work, resveratrol-loaded polycaprolactone (PCL) inhalable microspheres (MSs) were formulated to improve their therapeutic potential. The inhalable microspheres were formulated using the emulsion-solvent evaporation method. In this research, inhalable resveratrol microspheres were prepared using Tween 80 in place of polyvinyl alcohol which formed insoluble lumps. A 3 factorial design was applied taking polymer (PCL) and emulsifier (Tween 80) as independent variables and drug loading (DL) and encapsulation efficiency (EE) as dependent variables. The DL and EE of the optimized formulation were found to be 30.6% and 63.84% respectively. The in vitro aerosolization study performed using the Anderson cascade impactor showed that the fine particle fraction (FPF) of optimized resveratrol polycaprolactone microspheres (RSV-PCL-MSs) blended with lactose, and RSV-PCL-MSs were significantly higher than those of the pure drugs. The MMAD (theoretical mass median aerodynamic diameter) of optimized RSV-PCL-MSs was found to be 3.25 ± 1.15. The particle size of microspheres was within the inhalable range, i.e., between 1 and 5 µm. The morphological analysis showed spherical-shaped particles with smooth surfaces. The in vitro release study showed sustained drug release from the microspheres for up to 12 h. The study concluded that resveratrol-loaded inhalable microspheres may be an efficient delivery system to treat COPD.