Chongqing rural settlements, which embody people’s wisdom of how to dwell in the mountainous ecological and natural systems, feature varying landscape patterns of agricultural livelihoods, with landscape images of the native land mirroring the unique ecological splendor. With the use of remote sensing images point cloud data and GIS information captured in the field, and in combination with the classification of macro topographic area level, meso watershed level, and micro settlement unit level, this study proceeds with the analysis of images and landscape indexes of the livelihood elements of traditional settlements to uncover the characteristics of the human-land relationship of rural settlements in different regions of Chongqing’s traditional settlements. Given these and based on the companionship between settlements and cropland and the cropland classification model, this study draws out four typical types of agricultural livelihood landscapes. It puts forward ideas for the conservation and development of livelihood landscape types. The study of the unique lifestyle and visual language of the settlement formed in the natural environment is of practical significance in portraying Chongqing’s agricultural, cultural landscape, promoting and guiding the conservation and development of regional cultural landscapes, raising the identity of the local culture, and shaping a harmonious and beautiful countryside.