Declines in habitat quality through the breeding season within a bird’s home-range can limit overall productivity. In environments where multiple breeding opportunities arise during the course of a season, these effects can be buffered by a shift to different breeding sites or habitats. We studied the distribution and habitat associations of a crop-nesting farmland bird, the Yellow Wagtail Motacilla flava, across an arable-dominated farming region in eastern England using both field-scale territory mapping and large-scale transect surveys. Surveys were repeated at monthly intervals to measure changes in both distribution and habitat use during the course of the season. The distribution of breeding birds changed markedly at both regional and field-scales, coinciding with a shift in crop preference. Initially, most territorial birds were recorded in autumn-sown cereal fields, but this crop was subsequently abandoned in favour of potato crops, which were more patchily distributed. Other habitat features influencing Yellow Wagtail distribution included local crop diversity, hedgerow presence and soil type, with organic soils supporting higher abundance than alluvial clays or silts. The mid-season switch in habitat associations might allow individuals to maximize the number of breeding attempts made in a single year by using multiple habitats sequentially. The use of multiple habitats could influence population regulation by buffering the effects of local within-season declines in habitat suitability. Seasonal habitat switching may be more prevalent than is currently recognized in seasonal environments.