In a global setting where the requirements for development equally address the economic viability but also social and environmental sustainability, the healthy and efficient growth of rural communities poses substantial challenges. Our paper focuses on specific conditions and constraints that influence the progress of agritourism business initiatives as viable entrepreneurial solutions for self-sustainable rural communities in Romania. To assess the impact of economic, social and tourism-related factors on agritourism entrepreneurship for Romanian counties during 2010–2015 periods, we conducted several Ordinary Least Square regression models. The results emphasize that economic indicators like regional GDP and kilometers of national roads have a positive influence on the number of agritourism business units; also, a positive impact on agritourism entrepreneurship was identified for tourism-related factors like: number of employees and corresponding salaries in tourism, total tourists, share of tourism firms and their turnover in total firms and turnover of the region, as well as preference of tourists for agritourism. The conclusions highlight the direct link between resilient agritourism entrepreneurship and sustainable development of the region and open further research directions.