Winter savory (Satureja montana L.) is an aromatic subshrub of significant medicinal and seasoning qualities. Winter savory herb yield and quality depend on various factors, including environmental and agronomic ones. The aim of the present study was to evaluate the effect of winter savory plantation establishment method (seedlings, herbaceous cuttings) on the morphological traits and raw material yield. A more uniform propagation material with better morphological parameters was produced using generative propagation relative to vegetative propagation. A higher fresh and dry herb yield as well as a higher yield of herb without stems were obtained from plants grown from transplants compared to plants grown from vegetative cuttings. The essential oil content in the studied plants did not vary, but the oil yield was higher in plants grown from transplants compared to those derived from vegetative cuttings.