The goal of this study is to comprehensively evaluate the natural weathering performance of three wood species representing hardwood and softwood modified with the acetylation process. Alder (Alnus glutinosa L.), beech (Fagus sylvatica L.), and radiata pine (Pinus radiata D. Don) were characterised by various techniques to determine the aesthetical, chemical, and physical changes. The overall aesthetic performance of the investigated species was similar, with all showing a change in appearance after 9 months of exposure. However, the multi-sensor approach used for characterisation revealed differences in weathering behaviour related to surface erosion, wettability, and changes in chemical composition between the investigated species. An increase in the surface roughness observed for both hardwoods was associated with the erosion of the wood surface and the leaching of photodegraded chemical components. On the contrary, values of Sa remained relatively constant for acetylated radiata pine. Acetylated pine wood exhibited lower susceptibility to bleaching at the initial stage of the weathering process (3 months) and represented a more constant CIE L* compared to the investigated hardwood species. The contact angle measured with water gradually decreased in the case of acetylated radiata pine for up to six months, then it plateaued with a slight oscillation around 15°. For both hardwood species, the big drop was observed already after three months, followed by rather similar values. The PCA of IR spectra highlighted different mechanisms in the weathering of acetylated softwood and hardwood. The acetylated hardwood samples showed higher thermal stability than acetylated radiata pine. Experimental findings provide a comprehensive understanding of the long-term performance of acetylated wood, which directly influences its practical applications by enhancing design strategies, maintenance planning, product development, market acceptance, and overall sustainability. Performed tests have demonstrated the potential of underutilised hardwood species, enhanced through the acetylation process, to serve as alternative cladding materials to commonly used acetylated radiata pine.