As the core component of a wind turbine, the performance of main shaft bearings directly affects the transmission efficiency and reliability of wind turbines. To the best of our knowledge, few reliability analyses of wind power bearings have been carried out with the consideration of mechanical properties. In this paper, a finite element model is established to calculate the subsurface stress of the main shaft bearing of a wind turbine, considering the structural thicknesses, the friction conditions, and the interference conditions of the bearing. The randomness of several factors is considered, including structural thicknesses, material parameters, friction coefficients and the interference of the bearing. Latin hypercube design is used to get sample points, and the bearing’s mechanical responses of these sample points are analyzed. Through the data of these sample points, a Kriging model is established. The comparison with the finite element results shows that the Kriging model greatly improves the computational efficiency of the finite element model, with a relative error result of only 3.80 × 10−5. The Monte Carlo simulation method is applied to analyze the reliability and sensitivity of the bearing’s subsurface stress. The results show that an increase in the inner ring thickness will improve the bearing’s stress reliability, while an increase in other parameters will reduce the bearing’s stress reliability, including outer ring thickness, roller length, material elastic modulus, density, bearing and stationary shaft interference, and friction coefficients. The research results provide a reasonable reference for optimizing the design of the structure, assembly and material selection for main shaft bearings of wind turbines.