In naturally ventilated dairy barns, many questions regarding airflow, indoor air quality, and emissions are still unanswered, often resulting in inaccurate environmental control of the housing. Particularly, limited understanding of the implications of the constantly changing outdoor weather conditions in interaction with the building design and the role of the characteristics of the animals’ movement inside the building enhances uncertainties in the estimation of airflows within and across the barns. Computational fluid dynamics (CFD) have been used in the past to better understand the dynamics of barn climate, but the models are typically too slow to be used for real-time prediction and control. We investigated the effect of animal characteristics (i.e., animal location, orientation, body posture, and dimensions) on the pressure drop in the animal occupied zone considering inlet wind speed from 0.1 m s−1 to 5 m s−1 and wind direction of 0° and 90° in a CFD model. The cow position in general had little impact on the pressure drop at low wind speeds, but became relevant at higher wind speeds. Cows distributed in a more organized alignment showed less airflow resistance, and, therefore, a lower pressure drop and higher air velocities. Moreover, the cow breed affected the pressure drop, with higher withers resulting in a higher pressure drop and air resistance. In contrast, the effects of cow lying–standing ratio on the pressure drop and airflow resistance coefficients were negligible for both investigated wind directions. Our study aims to provide guidance for optimizing parametrizations of the animal occupied zone in order to enhance the speed of simulations without significant loss in model accuracy. In addition, the conclusions drawn from our study may support the adaption of building design and herd management to improve the effectiveness of ventilation concepts of naturally ventilated dairy barns.