The microbiota of dairy cow milk varies with the season, and this accounts in part for the seasonal variation in mastitis-causing bacteria and milk spoilage. The microbiota of the cowshed may be the most important factor because the teats of a dairy cow come into contact with bedding material when the cow is resting. The objectives of the present study were to determine whether the microbiota of the milk and the cowshed vary between seasons, and to elucidate the relationship between the microbiota. Methods: We used 16S rRNA gene amplicon sequencing to investigate the microbiota of milk, feces, bedding, and airborne dust collected at a dairy farm during summer and winter. Results: The seasonal differences in the milk yield and milk composition were marginal. The fecal microbiota was stable across the two seasons. Many bacterial taxa of the bedding and airborne dust microbiota exhibited distinctive seasonal variation. In the milk microbiota, the abundances of Staphylococcaceae, Bacillaceae, Streptococcaceae, Microbacteriaceae, and Micrococcaceae were affected by the seasons; however, only Micrococcaceae had the same seasonal variation pattern as the bedding and airborne dust microbiota. Nevertheless, canonical analysis of principle coordinates revealed a distinctive group comprising the milk, bedding, and airborne dust microbiota. Conclusion: Although the milk microbiota is related to the bedding and airborne dust microbiota, the relationship may not account for the seasonal variation in the milk microbiota. Some major bacterial families stably found in the bedding and airborne dust microbiota, e.g., Staphylococcaceae, Moraxellaceae, Ruminococcaceae, and Bacteroidaceae, may have greater influences than those varied between seasons.