Roller bearings are key parts in different machineries. As one of the major incipient failure models in the bearings, the surface crack will be enlarged to be a large spalling failure. Moreover, the abrupt changes in the contact characteristics caused by the crack zone would produce unacceptable impulses, which can affect the bearing vibrations. Thus, a study of the contact characteristics and vibrations of the bearings including the surface crack could be conducive for the incipient fault monitoring methods. To overcome this issue, a finite element model is proposed to obtain the influences of the depth and slope angle of a surface crack on the contact characteristics in a roller bearing. The relationships between the contact characteristics (contact deformation, width and stiffness) and crack sizes (depth and slope angle) are established. To study the influences of the surface crack sizes on the bearing vibrations, a dynamic model of the roller bearing considering the surface crack is also proposed. An experiment is introduced to verify the proposed method. It seems that the crack depth and slope angle can greatly affect the contact and vibration characteristics of the bearing. This study provides a helpful numerical approach for understanding the contact and vibration characteristics of roller bearings with various surface cracks.