The conservation and management of forest areas require knowledge about their extent and attributes on multiple scales. The combination of multiple classifiers has been proposed as an attractive classification approach for improved accuracy and robustness that can efficiently exploit the complementary nature of diverse remote sensing data and the merits of individual classifiers. The aim of this study was to develop and evaluate multiple classifier systems (MCSs) within a cloud-based computing environment for multi-scale forest mapping in Northeastern Greece using passive and active remote sensing data. Five individual machine learning base classifiers were used for class discrimination across the three different hierarchy levels, and five ensemble approaches were used for combining them. In the case of the binary classification scheme in the upper level of the hierarchy for separating woody vegetation (forest and shrubs) from other land, the overall accuracy (OA) slightly increased with the use of the MCS approach, reaching 94%. At the lower hierarchical levels, when using the support vector machine (SVM) base classifier, OA reached 84.13% and 74.89% for forest type and species mapping, respectively, slightly outperforming the MCS approach. Yet, two MCS approaches demonstrated robust performance in terms of per-class accuracy, presenting the highest average F1 score across all classification experiments, indicating balanced misclassification errors across all classes. Since the competence of individual classifiers is dependent on individual scene settings and data characteristics, we suggest that the adoption of MCS systems in efficient computing environments (i.e., cloud) could alleviate the need for algorithm benchmarking for Earth’s surface cover mapping.