This article proposes to study the behavior of recent and efficient state-of-the-art deep-learning based image descriptors for contentbased image retrieval, facing a panel of complex variations appearing in heterogeneous image datasets, in particular in cultural collections that may involve multi-source, multi-date and multi-view Permission to make digital contents. For this purpose, we introduce a novel dataset, namely Alegoria dataset, consisting of 12,952 iconographic contents representing landscapes of the French territory, and encapsultating a large range of intra-class variations of appearance which were finely labelled. Six deep features (DELF, NetVLAD, GeM, MAC, RMAC, SPoC) and a hand-crafted local descriptor (ORB) are evaluated against these variations. Their performance are discussed, with the objective of providing the reader with research directions for improving image description techniques dedicated to complex heterogeneous datasets that are now increasingly present in topical applications targeting heritage valorization.