Recently, the dairy sector has been ever more affected by global warming. This study aimed to test a novel conductive cooling system for cattle that was successfully implemented and evaluated under summer thermally challenging weather conditions in Poland. The system consists mainly of the chiller, tank, and chilled water-driven mattress, designed to prioritize animal well-being. The experimental evaluation was carried out on three Friesian dry cows, housed on different types of bedding—commercial water mattress, straw, and cooling water mattress—and supplied with water at 10 °C (day) and 16 °C (night). The cooling water mattress’ surface temperature was twice as low as that of the commercial water mattress. The animal’s thermal comfort was assessed with physiological and behavioral reactions. The cooling effect on animals’ bodies was demonstrated with a lower reticulorumen temperature of the cooled cow (p < 0.05) than the reference ones. The local effect of cooling was proved with an 8 °C-lower skin temperature after the cow’s resting period. The presented study opens a new research direction toward dairy cattle’s welfare, sustainability, and the food–energy–water nexus, based on potential energy and water savings.