In eastern Germany, the Czech Republic, and Slovakia, historic policies led to large, monocropped agricultural landscapes resulting in degradation of traditional landscapes. In the last 20 years, the expansion of urban and industrial areas has added to this degradation. The growing interest in nature‐based solutions, including water‐retention measures, is a response to reversing landscape degradation, rejuvenating ecosystem services, and mitigating the impacts of large‐scale commercial agriculture and climate change. In this study, the costs and benefits of water‐retention measures in eastern Germany, the Czech Republic, and Slovakia are assessed. Results indicate that water‐retention measures offer increased water availability over all land use classes assessed, help increase crop productivity, and aid in landscape cooling. Croplands are suggested as being the best value for money, offering the greatest volume potentials (mean = 88 million m3), cooling effects (mean = −1.6°C), and productivity gains (mean = €66 million yr−1), while also being the cheapest to implement per unit area. Differing policies in the three states will likely result in non‐uniform selection or implementation of measures. Future work should focus on local‐level studies offering greater practical messages beyond the regional‐level analysis conducted here. This work contributes to the growing body of literature assessing the costs and benefits of water‐retention measures, including the potential for landscape cooling, lowering temperature gradients, and ecosystem restoration. As the world urbanises, and as more land is converted to homogeneous cropland, such measures may prove critical in mitigating climate change, landscape drying, flood runoff, and soil and nutrient loss.