We use the Dyngjusandur sandsheet, Iceland as a testbed to quantify the type of data necessary to accurately represent ventifact orientations and extract paleowind information through a statistical evaluation of the differences between photogrammetric based and in situ geological analysis. Forty representative ventifacts were selected for in situ measurement, 20 of which were imaged for photogrammetric analysis to produce oriented and scaled virtual 3D models. An additional set of measurements were made on the “synthetic” models to allow for statistical assessment of erosional feature orientation. Despite the similarity between the photogrammetric (1145 measurements), and the in situ datasets (500 measurements), there are small, but significant differences that become more pronounced as sample size is reduced. Results indicate that in situ and photogrammetric methods of measuring feature orientation are comparable (to within 2° ± 2° at 1σ [N = 20] for inferring paleowind directions), but photogrammetric analyses requires less time for data acquisition (by a factor of 0.36–0.66) and yields over five times (5.16×) as many measurements per ventifact, with additional advantages of being able to examine digital objects under different illumination conditions, magnifications, and from angles that are otherwise not possible in the field. This data collection includes in situ and photogrammetric ventifact orientation measurements (.csv files), ventifact field images (.jpgs) and ventifact point cloud files (.bin and other format) collected during 2019 field work.