To better understand how moisture content (MC) affects the longitudinal compressive mechanical properties of bamboo, mechanical tests on both the macroscopic and cellular levels were performed on Moso bamboo (Phyllostachys pubescens Mazei ex H. de Lebaie) at different MCs. At the macroscopic level, the compressive modulus of elasticity (CMOE) was determined using a common mechanical tester, while the indentation modulus of elasticity (EIT) and the hardness (HIT) of the bamboo fiber cell walls were obtained using nanoindentation. The results showed that CMOE, EIT, and HIT were all negatively correlated with the change in MC below the fiber saturation point (FSP) with strong linear relationships. However, the CMOE was found to be more sensitive to a change in MC than was EIT, which indicated that the bamboo was more sensitive to MC at the macro level than at the cellular level, at least in terms of longitudinal compression stiffness. Moreover, EIT was found to be much less sensitive to a change in MC than was HIT, which may explain why the longitudinal compression strength of bamboo was much more sensitive to changes in MC than was the compression modulus of elasticity on the macro scale.