The peanut is mostly grown in semi-arid tropical regions of the world, characterized by unpredictable rainfall amounts and distribution. Average annual precipitation in the Virginia–Carolina (VC) region is around 1300 mm; however, unpredictable distribution can result in significant periods of water deficit and subsequent reduction in yield and gross income. The development of new peanut cultivars with high yield and acceptable levels of yield stability across various water-availability scenarios is an important component of the peanut breeding program in Virginia and the Carolinas, where the large-seeded Virginia-type peanut is the predominantly grown market type. In addition, the simultaneous use of runner cultivars developed in the dryer southeastern region has been proposed as a practical solution to limited irrigation availability in the VC region. Still, the identification and adequate utilization of available commercial cultivars with the best combination of yield, drought tolerance, and gross income is more immediately beneficial to the peanut industry, yet this assessment has not been carried out to date. The aim of this study was to identify cultivars that maintain high yield and grade, therefore gross income, across a wide range of environmental conditions. We evaluated five commercially available Virginia and runner-type peanut cultivars for pod yield stability using multilocation trials over four years across 13 environments. Additive main effects and multiplicative interaction (AMMI) and different stability approaches were used to study genotype (G), environment (E), and their interaction (G × E) on pod yield. Pod yield stability was specifically assessed by using the Lin and Binn approach, Wricke’s ecovalence, Shukla’s stability, and the Finlay–Wilkinson approach. The combined analysis of variance showed highly significant effects (p ≤ 0.001) for genotypes, environments, and G × E for pod yield. The environments varied in yield (2840–8020 kg/ha). Bailey, Sullivan, and Wynne are Virginia-type cultivars. The grade factors SMK, SS, and TK changed with water regime within both market types. Among the runner cultivars, TUFRunner 297 presented high mean productivity; however, it showed specific adaptation to limited environmental conditions. Based on different stability approaches, this study concludes that Sullivan and Bailey are the most stable and adaptable cultivars across the testing environments, whereas Wynne exhibited specific adaptability to some environments. These findings have important implications for peanut cultivar recommendations in terms of meeting peanut industry standards for yield, grading quality, and breeding progress.