Human interactions with ecosystems create numerous benefits. Until recently, the cultural benefits of ecosystem services had received less attention than environmental goods and economic opportunities, even though cultural ecosystem services (CES) are recognised as having important roles to play in supporting human well-being. In this chapter, we explore CES through the spatial lens of rural-urban relations, with the aim to move beyond traditional approaches looking at well-being benefits that urban dwellers might derive from rural “containers” of ecosystem services. Rather, we are interested in rural-urban relations as a locus for cultural ecosystem services that reveals complexity and multiplicity, interdependency and inequity. By drawing on three descriptive case studies—Garfagnana (Italy), the Cambrian Mountains (Wales) and Snowdonia (Wales)—we offer different views into the ways that CES emerge at the interface between environmental spaces and cultural practices. In particular, we highlight the potential for trade-offs, inequity and contestation. By reflecting on the complexities that arise from the rural-urban perspective on CES, we contribute to an emerging research agenda on territorial well-being.