Oxidized cellulose nanocrystals with sodium carboxylate groups (TOCNC-COONa) and with free carboxyl groups (TOCN-COOH) were prepared and then chemically modified with beta-cyclodextrin (βCD) and hydroxypropyl-beta-cyclodextrin (HPβCD) to prepare materials able to load and release antibacterial molecules over a prolonged period of time. The materials were characterized by infrared spectroscopy, and the CD content of modified TOCNCs determined by phenolphthalein colorimetry. The extent of grafting was also assessed by QCM-D and microscopy was used to ascertain and compare the morphology of both TOCNC-COONa/HPβCD and TOCNC-COOH/HPβCD. Then, carvacrol and curcumin were entrapped by the attached HPβCD and their prolonged release confirmed, as compared to neat material. The combined effects of HPβCD and carvacrol on the antimicrobial properties of TOCNC-COOH films were finally evaluated.