This article focuses on problematics of creating digital orthophotos using historical aerial photos. The project is part of a grant project that deals with change in rural architecture over the last two centuries. The orthophotos are one of the outputs created in the grant project and illustratively represent development of the selected villages over the last 80 years. In addition to orthophotos other outputs such as analytical map data (development of selected villages since the years around 1830 till present) are created. The article describes the current state of orthophoto creation and also difficulties that might be encountered at processing of historical photos. The specificity of this project is in small areas (primarily built-up areas of selected villages) that are processed. Such an area is usually captured only in one or two photos, which significantly affects the way of the photogrammetric processing. The project involves three preselected villages. Orthophotos are created for each of them in three terms (approximately 1938 + 1970 + 1985) and this chronological order is amended with purchased data for the year 1953 and the present. The time series of orthophotos, together with other inputs, bring better understanding to the development of rural settlements in the context of socio-historical events – e.g. Second World War, socialist expropriation, collectivization, agricultural large-scale production, changes in ownership after 1989 etc.