The morphology of road cut slopes, such as length and high slopes, is one of the most prevalent causes of landslides and terrain stability troubles. Digital elevation models (DEMs) and orthoimages are used for land management purposes. Two flights with different orientations with respect to the target surface were planned, and four photogrammetric projects were carried out during these flights to study the image orientation effects. Orthogonal images oriented to the cut slope with only sidelaps were compared to the classical vertical orientation, with sidelapping, endlapping, and both types of overlapping simultaneously. DEM and orthoimages obtained from the orthogonal project showed smaller errors than those obtained from the other three photogrammetric projects, with the first one being much easier to manage. One additional flight and six photogrammetric projects were used to establish an objective criterion to locate the three ground control points for georeferencing and rectification DEMs and orthoimages. All possible sources of errors were evaluated in the DEMs and orthoimages.