This study investigated the effects of parity, season, and the previous lactation's milk yield on fertility in dairy cows. A total of 5,514 calving records for Holstein cows that calved between 2016 and 2018 on a single large dairy farm in Japan were used for analysis. The proportion of cows that get pregnant by 360 days after calving was defined as the percentage of all cows eligible for breeding that became pregnant. In the all‐cow model, pregnancy probability associated with both parity and calving season (p < 0.05). Pregnancy probability decreased with an increase in parity, with hazard ratios (HRs) of 1.75 (1.58–1.94) for parity 1, 1.25 (1.13–1.39) for parity 2, 1.15 (1.04–1.29) for parity 3, and 1.13 (1.00–1.27) for parity 4, relative to parity ≥5. In terms of calving season, the lowest pregnancy probability was found in spring, and the HRs relative to spring were 1.16 (1.07–1.26) for summer, 1.35 (1.24–1.47) for autumn, and 1.17 (1.07–1.27) for winter. In the multiparous‐cow model, pregnancy probability associated with the previous lactation's milk yield (p < 0.05), but not with parity or calving season. Cows with high and middle previous milk yields had lower pregnancy probabilities than those with low milk yields.