Determining the grade of semantic similarity between geospatial concepts is the basis for evaluating semantic interoperability of geographic information services and their users. Geometrical models, such as conceptual spaces, offer one way of representing geospatial concepts, which are modelled as n-dimensional regions. Previous approaches have suggested to measure semantic similarity between concepts based on their approximation by single points. This paper presents a way to measure semantic similarity between conceptual regions—leading to more accurate results. In addition, it allows for asymmetries by measuring directed similarities. Examples from the geospatial domain illustrate the similarity measure and demonstrate its plausibility.