The Great Wall Villages (GWVs) are linked to the Great Wall in history, culture, and ecology. The cultural landscape resilience of Great Wall Villages (CLRGWVs) is distinctly significant. However, it is influenced by urbanization, pollution, and a lack of awareness of cultural landscape protection. Therefore, conservation and development practices still lack scientific strategies and guidance. This study proposes a new assessment system to quantify CLRGWVs, an analysis of the main influencing factors of resilience, and optimization paths to maintain sustainable development. Based on the socio-ecological system, this research designed the assessment with three criteria, eleven factors, and thirty-three indexes from the perspective of CLRGWVs. Furthermore, a demonstration test was constructed in Ningyuanbao Village, Dushikou Village, and Longmensuo Village in Chicheng County, Hebei Province, China. The results showed that there is some disparity between the three GWVs, with the resilience score of Dushikou Village being the highest in terms of resistance and learning. In contrast, Ningyuanbao Village’s resilience score is the lowest since resistance, recovery, and learning capacity are lower than in Dushikou and Longmensuo. Some influencing factors were found to be highly related to adaptive capacity. Lastly, some low-resilience aspects were identified as critical improvement targets for which corresponding optimization strategies should be proposed. This could be applied to streamline resilience optimization paths according to local conditions. This paper provides new ideas and directions for dealing with the sustainable development of villages and the conservation of cultural landscapes. It will also help villages deal with the relationship between socio-economic development and the conservation of cultural landscapes.