In this study, the emphasis is on assessing how satellite-derived vegetation indices respond to drought stress characterized by meteorological observations. This study aimed to understand the dynamics of grassland vegetation and assess the impact of drought in the Wielkopolskie (PL41) and Podlaskie (PL84) regions of Poland. Spatial and temporal characteristics of grassland dynamics regarding drought occurrences from 2020 to 2023 were examined. Pearson correlation coefficients with standard errors were used to analyze vegetation indices, including NDVI, NDII, NDWI, and NDDI, in response to drought, characterized by the meteorological parameter the Hydrothermal Coefficient of Selyaninov (HTC), along with ground-based soil moisture measurements (SM). Among the vegetation indices studied, NDDI showed the strongest correlations with HTC at r = −0.75, R2 = 0.56, RMSE = 1.58, and SM at r = −0.82, R2 = 0.67, and RMSE = 16.33. The results indicated drought severity in 2023 within grassland fields in Wielkopolskie. Spatial–temporal analysis of NDDI revealed that approximately 50% of fields were at risk of drought during the initial decades of the growing season in 2023. Drought conditions intensified, notably in western Poland, while grasslands in northeastern Poland showed resilience to drought. These findings provide valuable insights for individual farmers through web and mobile applications, assisting in the development of strategies to mitigate the adverse effects of drought on grasslands and thereby reduce associated losses.