Vineyard cottages must remain a typological characteristic of vineyard areas in Dolenjska Region, as a historical, ethnological and architecture reflection of the cultural landscape. In the past, vineyard cottages represented a logically situated architectural design structures, created by simple peasants, according to laws of nature. Later on, vineyard cottage design has become more and more the consequence of socioeconomic relationships and technological development. The vineyard cottage owners have been mostly self-taught designers and architects, which has resulted in illegal construction. Thus, the consequence is a variety of construction types of over-dimensioned and inadequate structures, which cannot be legalised today on the basis of applicable spatial provisions. The provisions of the spatial plan that enable legalisation are strict and mostly do not consider the As-Is status, which is a spatial fact. In order to regulate legal status of the vineyard cottages (acquiring building permits), we developed a structure remediation model, which on the basis of selected criteria and through the development procedure as well as adoption of a Municipal Detailed Spatial Plan, enables the fulfilment of conditions for legalisation. In spite of the fact that the mentioned model takes into consideration a comprehensive approach to spatial planning, it results mostly in preserving the current status. In order to improve the spatial status and not only preserve it, an upgraded model, which will, under the more detailed design provisions, gradually (not overnight) return to Dolenjska hills the status of quality cultural landscape, has been proposed.