Landslides are a widespread natural phenomenon that play an important role in landscape evolution and are responsible for several casualties and damages. The Abruzzo Region (Central Italy) is largely affected by different types of landslides from mountainous to coastal areas. In particular, the hilly piedmont area is characterized by active geomorphological processes, mostly represented by slope instabilities related to mechanisms and factors that control their evolution in different physiographic and geological–structural conditions. This paper focuses on the detailed analysis of three selected case studies to highlight the multitemporal geomorphological evolution of landslide phenomena. An analysis of historical landslides was performed through an integrated approach combining literature data and landslide inventory analysis, relationships between landslide types and lithological units, detailed photogeological analysis, and geomorphological field mapping. This analysis highlights the role of morphostructural features on landslide occurrence and distribution and their interplay with the geomorphological evolution. This work gives a contribution to the location, abundance, activity, and frequency of landslides for the understanding of the spatial interrelationship of landslide types, morphostructural setting, and climate regime in the study area. Finally, it represents a scientific tool in geomorphological studies for landslide hazard assessment at different spatial scales, readily available to interested stakeholders to support sustainable territorial planning.