The degradation of pastures and meadows is a global problem with a wide range of impacts. It affects farmers in different ways, such as decreases in cattle production, milk yield, and forage quality. Still, it also has other side effects, such as loss of biodiversity, loss of resources, etc. In this study, the degradation of a semi-natural pasture near the village of Obichnik, Bulgaria, was evaluated using machine learning algorithms, and an unmanned aerial vehicle (UAV) obtained visual spectrum images. A high-quality (HQ) orthomosaic of the area was created and numerous regions of interest were manually marked for training and validation purposes. Three machine learning algorithms were used—Maximum likelihood, Random trees (RT), and Support Vector Machine (SVM). Furthermore, object-based and pixel-based approaches were utilized. The obtained results indicate that the object-based RT and SVM models provide significantly better accuracy, with their Cohen’s Kappa reaching 0.86 and 0.82, respectively. The performed classification showed that approximately 61% of the investigated pasture area is covered with grass, which indicates light-to-medium degradation.