The development of the stormwater management strategies, e.g., low-impact development (LID), water-sensitive urban design (WSUD), and sustainable drainage solutions (SUDS), was initiated in the mid-1980s as a set of engineering approaches and technologies to reduce the harmful effects of stormwater. Over time, all of them evolved in the holistic, multidisciplinary approaches and, today, they are increasingly viewed and implemented under the umbrella term “Nature-based Solutions” (NbS). The technical elements and measures of these NbS represent various technical solutions, implemented i.a., according to the suitability of the site to achieve their maximum efficiency. Currently, there are no standards or procedures for the application of NbS technologies in Serbia. To overpass this and encourage implementation, we carried out preliminary assessment of NbS elements suitability for application in eight urban settlements in the Region of Southern and Eastern Serbia. The assessment is based on publicly available data and performed according to the existing recommendations in the field of spatial planning and rainwater management for WSUD. The analyses were conducted by GIS tools that involved spatial analyses of various terrain characteristics and provided an insight into the criteria, i.e., constraints that are key to the placement of various technical elements, including bioretention, rain garden, and permeable pavement. Research findings point out that creation of the thematic maps with area suitability ratings for individual NbS stormwater elements might represent a good starting point for further investigation, planning, and design. The proposed framework for preliminary assessment is potentially useful for the countries and regions without regulations in the field of NbS for stormwater management.