Major losses of agricultural production and soils are caused by erosion, which is especially pronounced on hillslopes due to specific hydrological processes and heterogeneity. Therefore, the aim of this study was to assess the impact of agricultural management on the compaction, infiltration, and seasonal water content dynamics of the hillslope. Measurements were made at the hilltop and footslope, i.e., soil water content and potential were measured using sensors, wick lysimeters were used to quantify water flux, while a mini-disk infiltrometer was used to measure the infiltration rate and calculate the unsaturated hydraulic conductivity (K_unsat). Soil texture showed differences between hillslope positions, i.e., at the hilltop after 50 cm depth, the soil is classified as silty clay loam, and from 75 cm onward, the soil is silty clay, while at the footslope, the soil is silt loam even at the deeper depths. The results show a higher K_unsat at the footslope as well as higher average water volumes collected in wick lysimeters compared to the hilltop. Average water volumes showed a statistically significant difference at p < 0.01 between the hilltop and the footslope. The soil water content and water potential sensors showed higher values at the footslope at all depths, i.e., 8.0% at 15 cm, 8.4% at 30 cm, and 27.3% at 45 cm. The results show that, even though the vineyard is located in a relatively small area, soil heterogeneity is present, affecting the water flow along the hillslope. This suggests the importance of observing water movement in the soil, especially today when facing extreme weather (e.g., short-term high-intensity rainfall events) in order to protect soil and water resources.