A trade-off exists for migrating animals as to whether to migrate or remain residents. Few studies have documented relationships between landscape variables and deer migration strategies. From 2000 to 2007 we captured 267 adult female white-tailed deer (Odocoileus virginianus) at 7 study sites in Minnesota and South Dakota and monitored 149 individuals through ≥3 seasonal migration periods (585 deer-migration seasons). All deer classified as obligate migrators with ≥3 migrations (range 3–9 migration seasons) maintained their obligate status for the duration of the study. Multinomial logistic odds ratios from generalized estimating equations indicated that the odds of being a resident increased by 1.4 and 1.3 per 1-unit increase in forest patch density and mean area, respectively, compared to migrating deer. Odds of being an obligate migrator increased by 0.7 and 0.8 per 1-unit decrease in forest patch density and mean area, respectively, compared to resident or conditional migrating deer. Areas inhabited by resident deer were characterized by greater number of forest patches per 100 ha and larger mean forest patch area than conditional and obligate migrant areas. Odds of migrating increased by 1.1 per 1-unit increase in deer winter severity index. Migration behavior of white-tailed deer varied among regions, and land-cover and landscape characteristics provided predictive indicators of migration strategies for deer that could have important implications for conservation, metapopulation dynamics, and species management.