Cultural heritage is one of the most exceptional resources characterizing the Italian territory. Archaeological heritage, i.e., the archaeological sites with different types of archaeological artifacts, strongly contributes to enriching the national and international cultural heritage. Nevertheless, it is constantly exposed to external factors, such as natural deterioration, anthropic impact, and climate-related hazards, which may compromise its conservation. In Italy, many archaeological areas are affected by significant soil settlements that involve a large part of monuments. This paper focuses on the landslide hazard assessment of the archaeological site of Pietrabbondante (Molise region, Italy). The impact of the expected rainfall regimes, according to the EURO-CORDEX projections, on slope stability conditions were evaluated through the application of a physically based model that couples a hydraulic and a mechanical model to evaluate slope stability evolution due to pore pressure changes. Given the unavoidable lack of knowledge of the geotechnical soil properties in an archaeological heritage area, the proposed method considered the random uncertainty of soil parameters by means of a probabilistic approach in order to assess the stability conditions in terms of probability of occurrence of a landslide. The results of this study provide a reference for the safety assessment and preventive conservation of archaeological areas characterized by high cultural value.