In the perusal of our endeavour towards the synthesis of new bioactive agents, a new series of substituted (1‐(4‐chlorobenzyl)‐1H‐indol‐3‐yl) 1H‐(1,2,3‐triazol‐4‐yl) methanones (8a‐u) were designed, synthesized and investigated for their antimicrobial activity with special emphasis on their anti‐Candida potential and Candida biofilm inhibition. Among them, the hybrids 8e, 8f, and 8o demonstrated significant antifungal activity on most of the tested fungal strains with MIC values ranging between 1.9–7.8 μg/mL. In addition, the most promising compounds were found to be effective biofilm inhibitors. We have studied the Field emission Scanning Electron Microscope (FE‐SEM) micrographs for 8f to know the damage of the cells with altered membrane integrity and release of intracellular contents thereby validating the in vitro biofilm inhibition assay. Further, in enzymatic assay, active compounds inhibited ergosterol biosynthesis. Furthermore, docking studies revealed that they effectively bind to 14α‐demethylase (CYP51), thereby inhibiting ergosterol biosynthesis. Interestingly, they exhibited lower cytotoxicity in the normal cell line (MRC5).