Digital surface models (DSMs) are widely used in forest science to model the forest canopy. Stereo pairs of very high resolution satellite and digital aerial images are relatively new and their absolute accuracy for DSM generation is largely unknown. For an assessment of these input data two DSMs based on a WorldView-2 stereo pair and a ADS80 DSM were generated with photogrammetric instruments. Rational polynomial coefficients (RPCs) are defining the orientation of the WorldView-2 satellite images, which can be enhanced with ground control points (GCPs). Thus two WorldView-2 DSMs were distinguished: a WorldView-2 RPCs-only DSM and a WorldView-2 GCP-enhanced RPCs DSM. The accuracy of the three DSMs was estimated with GPS measurements, manual stereo-measurements, and airborne laser scanning data (ALS). With GCP-enhanced RPCs the WorldView-2 image orientation could be optimised to a root mean square error (RMSE) of 0.56 m in planimetry and 0.32 m in height. This improvement in orientation allowed for a vertical median error of −0.24 m for the WorldView-2 GCP-enhanced RPCs DSM in flat terrain. Overall, the DSM based on ADS80 images showed the highest accuracy of the three models with a median error of 0.08 m over bare ground. As the accuracy of a DSM varies with land cover three classes were distinguished: herb and grass, forests, and artificial areas. The study suggested the ADS80 DSM to best model actual surface height in all three land cover classes, with median errors < 1.1 m. The WorldView-2 GCP-enhanced RPCs model achieved good accuracy, too, with median errors of −0.43 m for the herb and grass vegetation and −0.26 m for artificial areas. Forested areas emerged as the most difficult land cover type for height modelling; still, with median errors of −1.85 m for the WorldView-2 GCP-enhanced RPCs model and −1.12 m for the ADS80 model, the input data sets evaluated here are quite promising for forest canopy modelling.