The aim of the study was to examine combinations of base oils and herbal additives with a view to obtaining macerates with improved health benefits. Base oils were cold-pressed from the seeds of black cumin, borage, evening primrose, safflower, walnut, common hazel, and oilseed rape, as well as the flesh of sea-buckthorn fruits. They were then supplemented with herbs, including basil, thyme, and sage, in order to create macerates. Total antioxidant activity and tocopherol level were analyzed in oils, macerates, and oil cakes. Additionally, chemical properties of oil cakes—such as the level of fibre, vitamin C, β-carotene, and lutein—were also examined. Supplementation with herbs caused diversified effects on antioxidant activity and tocopherol level in macerates depending on the base oil, herb, and supplementation method. The obtained results indicate that tocopherol level does not play a decisive role in determining the antioxidant properties of oils, macerates, and oil cakes, suggesting significant involvement of other antioxidants. Among the tested macerates, the most promising one seems to be oilseed rape oil enriched with sage or basil to maximize its health benefits. The study can serve as a starting point for the development and implementation of functional macerates and oil cakes in healthy nutrition.