The study of the adhesion of solid and liquid aqueous phases to superhydrophobic surfaces has become an attractive topic for researchers in various fields as a vital step in the design of icephobic coatings. The analysis of the available results shows that the experimentally measured values of adhesion strength for superhydrophobic substrates, which in some cases are quite small, are still essentially higher than might be expected from the portion of the actual wetted area. In this study we have considered the peculiarities of the three-phase contact zone between sessile supercooled water or ice droplets and a superhydrophobic coating at negative temperatures (below 0 °C) and during the water-ice phase transition. Two types of superhydrophobic coatings with very different textures were used to analyze the evolution of shape parameters of a sessile water droplet during droplet cooling and freezing. It was shown that the evolution of the contact angle and droplet contact diameter of a water droplet deposited on a superhydrophobic surface does not undergo essential changes when the droplet is cooled simultaneously with the substrate and the surrounding environment, and the humidity is maintained close to 100% during the cooling process. However, the phase transition from supercooled water to ice droplets leads to the growth of a metastable iced meniscus and a frost halo in the vicinity of the three-phase contact zone. The meniscus effectively increases the area of adhesive contact between the droplet and the substrate. This phenomenon is intrinsically related to the release of the heat of crystallization and is responsible for the enhancement of adhesion to a superhydrophobic substrate upon droplet transition from supercooled water to ice. At the same time, it was shown that the metastable state of the above meniscus leads to its spontaneous sublimation during exposure at negative temperatures.