The brown marmorated stink bug, Halyomorpha halys Stål (Hemiptera: Pentatomidae), is native to Japan, China, Taiwan, and Korea. Its dispersion from Asia to the United States of America and Europe caused serious damage to fruit, vegetables, and high-value crops. In Greece, damages are reported in kiwi orchards in the regions of Pieria and Imathia, which are the main production areas of kiwifruit. Greek kiwifruit production is expected to increase twofold within the next years. The aim of this research is to study the terrain and canopy properties that may have an impact on the development of H. halys populations. Thus, five kiwi orchards in total were selected in the regions of Pieria and Imathia. Τen traps were installed from early June to late October within each selected kiwi orchard–two types of traps at every side of the orchards and the center. The installed traps were examined weekly and the number of the captured H. halys was recorded. During the same days, sentinel satellite images were analyzed to calculate the vegetation index, NDVI (Normalised Difference Vegetation Index), and NDWI (Normalised Difference Water Index). The results showed population variability within the kiwi orchards since the population of H. halys was higher in areas with high NDVI and NDWI values. Additionally, our research revealed that H. halys prefers to develop populations at higher altitudes at both regional and field scales. The results of this research can be used to reduce damages by H. halys in kiwi orchards using different rates of pesticides depending on the prediction of the population size. There are multiple benefits of the proposed practice, such as a reduction in the production cost of kiwifruits, an increase in farmers’ profit, and environmental protection.