Structural health monitoring relies heavily on measurements. Entropy theory is emerging as a critical quantitative analysis technique for interpreting measured data for both health monitoring and fault identification of structural systems. This paper introduces the algorithms of weighted symbolic sequence entropy (WSSE) and its multi-weighted derivation, termed multi-weighted symbolic sequence entropy (MWSSE). WSSE optimizes the existing algorithms, including symbolic sequence entropy (SSE) and improved symbolic sequence entropy (ISSE), by introducing a weighting factor in the computation process of the algorithm. WSSE significantly contributes to enlarging the difference between normal and fault sequences of signals in rotary machinery. The multi-weighted derivation of WSSE, namely MWSSE, more effectively depicts the dynamical characteristics of rotary machinery by utilizing entropy values of multiple weighting factors as health indicators. The MWSSE-based degradation monitoring and fault identification approaches developed by the authors are validated through application research and comparative analysis. These novel entropy algorithms offer innovative quantitative analysis techniques for fault diagnosis in rotary machinery and structural health monitoring and hold potential for application in broader research fields.