<p>The distinct bimodularity characteristics of rock materials directly affect stress concentration and hole failure. In this study, the law of crack development around holes under bimodularity effects is investigated through the development of a discrete element method (DEM) and a calibration approach using the rock crack bond (RCB) contact model. Moreover, loading simulation experiments on rocks containing holes are conducted by the model. The results indicate that the model can simultaneously reproduce the mechanical properties of rocks under tensile, compressive, and shear loading. The development of tensile cracks is the main mechanism for the accumulation of damage in rocks during loading, whereas the development of shear cracks is the main mechanism that induces and guides crack propagation and specimen failure. An increase in the inclination angle of the holes promotes the sliding and dislocation of particles between the holes, enabling the radial deformation of the rock and the propagation of shear cracks. However, the unloading effect produced when the holes overlap in the direction of the principal stress reduces the contact stress of the particles between the holes and inhibits the propagation of shear cracks. The interaction between holes generates compressive–shear stress bridges that link their sides and tensile stress bridges that connect their top and bottom surfaces. Consequently, the resulting macroscopic cracks that penetrate the holes generally align with this stress bridge distribution.</p>