The phytochemical investigation of the leaves of Inula confertiflora, a medicinal plant endemic to Ethiopia, led to the isolation of 15 terpenoids; 1β‐hydroxy‐α‐costic acid (1), 3α‐hydroxycostic acid (2), isotelekin (3), asperilin (4), carabrone (5), carpesioline (6), graveolide (7), inuviscolide (8), 8‐epi‐inuviscolide (9), 1β,4β‐dihydroxy‐5α(H)‐guaia‐10(14),11(13)‐dien‐8α,12‐olide (10), isoinuviscolide (11), 4β,10β‐dihydroxy‐5α(H)‐1,11(13)‐guaidien‐8α,12‐olide (12), 4β,10β‐dihydroxy‐1β(H)‐5α(H)‐guai‐11(13)‐en‐8α,12‐olide (13), 4β,10α‐dihydroxy‐1β(H)‐5α(H)‐guai‐11(13)‐en‐8α,12‐olide (14), 4β,10α‐dihydroxy‐1α(H)‐5α(H)‐guai‐11(13)‐en‐8α,12‐olide (15). Herein, structural elucidation and full NMR data for compound 1 are presented for the first time. The structures were elucidated using NMR, HRESIMS, and by comparison with literature data. The relative configurations were defined by NOESY correlations and single‐crystal X‐ray crystallography. Herein, crystallography data of 6 and 7 were reported for the first time. The antibacterial efficacy of some of the isolated compounds was evaluated against two commonly dispersed environmental strains of Escherichia coli and Staphylococcus aureus. Compounds 1, 3, 6, 7, and 8 exhibited moderate antibacterial activities against the tested organisms. The chemotaxonomic significance of compounds is discussed.