Stink bugs, including Nezara viridula (L.), Euschistus servus (Say), and Chinavia hilaris (Say), are economic pests across agricultural farmscapes where they can colonize closely associated crops. This 4-yr on-farm study was conducted to examine the likelihood of these three stink bug species colonizing crops in corn—cotton, corn—peanut—cotton, and peanut-cotton farmscapes by using odds ratios. Corn (Zea mays L.), peanut (Arachis hypogaea L.), and cotton (Gossypium hirsutum L.) served as host plants for E. servus and N. viridula. Corn did not serve as a host plant for C. hilaris. Although peanut was a relatively poor host plant, cotton was a relatively good host plant for this stink bug. For N. viridula and E. servus adults, the risk of crop colonization was higher for peanut in peanut—cotton farmscapes with corn than without corn and was highest for cotton in corn—peanut—cotton, followed by peanut—cotton, and lastly corn—cotton farmscapes. The likelihood of oviposition by E. servus, though, was higher in cotton in corn—cotton than peanut—cotton farmscapes. For C. hilaris adults, the risk of crop colonization was highest for cotton in peanut—cotton, followed by corn—peanut—cotton, and lastly corn—cotton farmscapes. Corn was more likely than peanut or cotton to harbor adults and immatures, i.e., egg masses and young nymphs, of N. viridula and E. servus. Adults of all three stink bug species colonized cotton more often than peanut in peanut—cotton farmscapes. However, oviposition by N. viridula and E. servus occurred more often in peanut than in cotton. These assessments of the likelihood of stink bug colonization are essential for modeling predictions of stink bug colonization and designing more comprehensive landscape management approaches for control of stink bugs in these farmscapes.