This paper reviews evidence for medieval castles in the historic county of Rutland during the period c. 1066-1216, using a combination of archaeological, historical and topographical data. The siting of individual castle sites is analysed, the possibility of antecedent occupation is explored, and particular attention is devoted to the relationship between castle sites and associated features within the medieval landscape, including parish churches, settlement patterns and manorial earthworks. Throughout, it is emphasised that medieval castles can be understood most appropriately within the context of contemporary rural landscapes and urban townscapes.