Our study compared the behavior of prepartum dairy cows that either remained in an outdoor paddock until calving (OP) during winter or were moved to an indoor maternity pen either early (EM) or late (LM) relative to calving. Forty-two multiparous Holstein cows were divided into three treatments (OP, EM, or LM) and monitored from 3 weeks before to 1.5 h after calving. Cows in EM and LM were moved to a maternity pen starting at week three and week one before the expected calving date, respectively. We assessed the cleanliness of the cows at calving, immunoglobulin G concentration in colostrum, and the behavior and vitality of calves across treatments. Cows spent more time lying in EM compared to OP and LM during the weeks −3 and −2 relative to calving, but lying time was increased in LM cows compared with OP cows during the week −1 relative to calving. Prepartum rumination time was lowest in OP cows but not different between EM or LM. Calves from OP cows spent more time lying and had lower vitality after calving than those from LM and EM cows, respectively; calves from EM and LM cows were intermediate for lying and vitality, respectively, but did not differ from either group. The cleanliness was greatest in cows that calved indoors (EM or LM); nevertheless, precalving management did not affect the IgG concentration in colostrum. Our study demonstrates that, in comparison with OP, EM and LM have positive implications for the welfare of the dam and its newborn calf during winter.