Historically, cooperative medical insurance and village doctors are considered two powerful factors in protecting rural residents’ health. However, with the central government of China’s implementation of new economic policies in the 1980s, cooperative medical insurance collapsed and rural residents fell into poverty because of sickness. In 2009, the New Rural Cooperative Medical Insurance (NRCMI) was implemented to provide healthcare for rural residents. Moreover, the National Basic Drug System was implemented in the same year to protect rural residents’ right to basic drugs. In 2013, a village doctor contract service was implemented after the publication of the Guidance on Pilot Contract Services for Rural Doctors. This contract service aimed to retain patients in rural primary healthcare systems and change private practice village doctors into general practitioners (GPs) under government management. Objectives: This study investigates the factors associated with rural residents’ contract behavior toward village doctors. Further, we explore the relationships between trust, NRCMI reimbursement rate, and drug treatment effect. We used a qualitative approach, and twenty-five village clinics were chosen from three counties as our study sites using a random sampling method. A total of 625 villagers participated in the investigation. Descriptive analysis, chi-squared test, t-test, and hierarchical logistic analyses were used to analyze the data. Results: The chi-squared test showed no significant difference in demographic characteristics, and the t-test showed a significant difference between signed and unsigned contract services. The results of the hierarchical logistic analysis showed that trust significantly influenced patients’ willingness to contract services, and the drug treatment effect and NRCMI reimbursement rate moderated the influence of trust. Conclusion: Our findings suggest that the government should aim to strengthen trust in the doctor–patient relationship in rural areas and increase the NRCMI reimbursement rate. Moreover, health officers should perfect the contract service package by offering tailored contract services or expanding service packages.