An increasing number of studies directed at supercooling water droplets on surfaces with different wettabilities have appeared in recent years. This activity has been stimulated by the recognition that water supercooling phenomena can be effectively used to develop methods for protecting outdoor equipment and infrastructure elements against icing and snow accretion. In this article, we discuss the nucleation kinetics of supercooled sessile water droplets on hydrophilic, hydrophobic, and superhydrophobic surfaces under isothermal conditions at temperatures of -8, -10, and -15 °C and a saturated water vapor atmosphere. The statistics of nucleation events for the ensembles of freezing sessile droplets is completed by the detailed analysis of the contact angle temperature dependence and freezing of individual droplets in a saturated vapor atmosphere. We have demonstrated that the most essential freezing delay is characteristic of the superhydrophobic coating on aluminum, with the texture resistant to contact with ice and water. This delay can reach many hours at T = -8 °C and a few minutes at -23 °C. The observed behavior is analyzed on the basis of different nucleation mechanisms. The dissimilarity in the total nucleation rate, detected for two superhydrophobic substrates having the same apparent contact angle of the water drop but different resistivities of surface texture to the contact with water/ice, is associated with the contribution of heterogeneous nucleation on external centers located at the water droplet/air interface.