Assessing the holistic sustainability of public policies remains a challenge rarely taken up due to a lack of adequate assessing methods. Frequently, only environmental and/or financial aspects are addressed, rather than the three pillars, including macro- and micro-economic as well as social performance. This paper presents an assessment method to fully compare the performance of pavement resurfacing policies for all its stakeholders and considering pavement–vehicle interactions. First, an analytical and then systemic approach to road maintenance highlights all its stakeholders, and a complete set of sustainability indicators is proposed to quantify the various impacts of maintenance programs: tax revenues, road operator’s and users’ savings, domestic production and employment, net present value, users’ time savings and noise reduction health benefits, as well as protection of natural resources, biodiversity and human health. Second, specific physical models of road condition (International Roughness Index) and its role in pavement–vehicle interaction in terms of vehicle consumption and wear as well as traffic noise are introduced. Then, equations to calculate these indicators are presented based on a comparison of existing assessment methods. The final transdisciplinary method pulls from road engineering, industrial ecology, acoustics and economics. It especially combines environmental and economic life cycle assessments and economic input–output analysis, as well as financial and socioeconomic appraisals. Finally, this article takes up the interdisciplinary challenge of building a fully holistic assessment method to help decision makers properly address sustainability, and its general algorithm can be adapted to assess a variety of transportation policies.