Small landscape elements are critical in ecological systems, encompassing vegetated and non-vegetated features. As vegetated elements, hedgerows contribute significantly to biodiversity conservation, erosion protection, and wind speed reduction within agroecosystems. This study focuses on the semi-automatic extraction of hedgerows by applying the Object-Based Image Analysis (OBIA) approach to two multispectral satellite datasets. Multitemporal image data from PlanetScope and Copernicus Sentinel-2 have been used to test the applicability of the proposed approach for detailed land cover mapping, with an emphasis on extracting Small Woody Elements. This study demonstrates significant results in classifying and extracting hedgerows, a smaller landscape element, from both Sentinel-2 and PlanetScope images. A good overall accuracy (OA) was obtained using PlanetScope data (OA = 95%) and Sentinel-2 data (OA = 85%), despite the coarser resolution of the latter. This will undoubtedly demonstrate the effectiveness of the OBIA approach in leveraging freely available image data for detailed land cover mapping, particularly in identifying and classifying hedgerows, thus supporting biodiversity conservation and ecological infrastructure enhancement.