Interest in the well-being of people exposed to long-term violence and conflict has tended to focus on measurable effects of acute traumatic events, while attention to the pressures of their daily living context is relatively new. Using qualitative and quantitative data from a 2005 survey of all female family caretakers in 2 neighbouring Israeli-occupied West Bank villages (n = 820), we explored the associations of demographic, health-related and contextual factors with reported pressures and WHO-5 well-being index scores. The final model explained 17.8% of the variance with negative associations between health-related factors (“back-aches,” “stomach aches” “psychological illness in the family”) and family-related factors (“male head of household aggressive”, “male head of household physically violent”) and the WHO-5 well-being index scores. We found positive associations between socio-economic factors (“standard of living”; “number of rooms”) and village-related factors (“residency in village A/B”) and the WHO-5 well-being index score. Exploring the daily living context of villages A and B illuminated how the impact of historical and political events differed, even in villages that are geographically close. The paper lends support to calls for including politics and history in research on well-being in contexts of long-term violence and conflict.