Ice accumulation is a key and unsolved problem for many composite structures with polymer matrices, e.g., wind turbines and airplanes. One of the solutions to avoid icing is to use anti-icing coatings. In recent years, the influence of hydrophobicity of a surface on its icephobic properties has been studied. This solution is based on the idea that a material with poor wettability maximally reduces the contact time between a cooled drop of water and the surface, consequently prevents the formation of ice, and decreases its adhesion to the surface. In this work, a hybrid modification of a gelcoat based on unsaturated polyester resin with nanosilica and chemical modifiers from the group of triple functionalized polyhedral oligomeric silsesquioxanes (POSS) and double organofunctionalized polysiloxanes (generally called multi-functionalized organosilicon compounds (MFSC)) was applied. The work describes how the change of modifier concentration and its structural structure finally influences the ice phobic properties. The modifiers used in their structure groups lowered the free surface energy and crosslinking groups with the applied resin, lowering the phenomena of migration and removing the modifier from the surface layer of gelcoat. The main studies from the icephobicity point of view were the measurements of ice adhesion forces between modified materials and ice. The tests were based on the measurements of the shear strength between the ice layer and the modified surface and were conducted using a tensile machine. Hydrophobic properties of the obtained nanocomposites were determined by measurement of the contact angle and contact angle hysteresis. As the results of the work, it was found that the modification of gelcoat with nanosilica and multi-functionalized silicone compounds results in the improvement of icephobic properties when compared to unmodified gelcoat while no direct influence of wettability properties was found. Ice adhesion decreased by more than 30%.