Background: Family caregivers faced unprecedented circumstances and experienced increased levels of stress during the COVID-19 pandemic. Resourcefulness can minimize the effect of stress on health outcomes. Objectives: The purpose of this study was to examine the associations between caregiving stress during the pandemic, resourcefulness, and self-rated health and assess the mediating effect of resourcefulness. Methods: A convenience sample of 70 family caregivers of adults with chronic and/or disabling conditions was recruited using social media groups and professional networking platforms. Data were collected using an online survey and analyzed using linear regression. Mediation analysis was conducted using the PROCESS macro. Results: Higher levels of caregiving stress during the pandemic and lower levels of resourcefulness were associated with worse self-rated health, while controlling for age, employment status, and weekly caregiving hours. Resourcefulness mediated the relationship between caregiving stress and self-rated health. Our findings highlight the importance of assessing the psychological impact of the pandemic on family caregivers’ outcomes. Conclusions: Resourcefulness skills can be targeted to improve the health and well-being of family caregivers during and beyond the pandemic.