The deterioration of the performance of polysaccharide-based films over time, particularly their hydrophilicity and mechanical properties, is one of the main problems limiting their applications in the packaging industry. In the present study, we proposed to improve the performance of chitosan-based films through the use of: (1) nanocellulose as an additive to reduce their hydrophilic nature; (2) bio-based plasticizer to improve their mechanical properties; and (3) chestnut extract as an antimicrobial agent. To evaluate their stability over time, the properties of as-formed films (mechanical, hydrophilic, barrier and antibacterial) were studied immediately after preparation and after 7, 14 and 30 days. In addition, the morphological properties of the films were characterized by scanning electron microscopy, their structure by FTIR, their transparency by UV-Vis and their thermal properties by TGA. The films showed a hydrophobic character (contact angle above 100°), barrier properties to oxygen and carbon dioxide and strong antibacterial activity against Gram-negative (E. coli) and Gram-positive (S. aureus) bacteria. Moreover, the use of nanofillers did not deteriorate the elongation at breaks or the thermal properties of the films, but their addition reduced the transparency. In addition, the results showed that the greatest change in film properties occurred within the first 7 days after sample preparation, after which the properties were found to stabilize.