Women living with HIV (WLHIV) in the United States experience higher rates of death from cervical and breast cancer and lower screening rates for both compared to women without HIV. These disparities highlight the need to better understand access to and uptake of women's preventive health services-particularly cervical cancer screening, breast cancer screening, and HPV vaccination. Most existing data on these services among WLHIV come from urban settings; therefore, the purpose of this study was to investigate factors affecting adherence to these preventive health measures among WLHIV in Vermont, a rural state with unique healthcare challenges. This cross-sectional study included a retrospective analysis of electronic medical record (EMR) data and a one-time quantitative survey. The EMR analysis assessed cervical Papanicolaou (Pap) smear, mammography, and human papillomavirus (HPV) vaccination rates among WLHIV and women without HIV enrolled in care at University of Vermont-affiliated sites from January 2017 to December 2020. The survey collected demographic information and details regarding care received from WLHIV. Among 98 WLHIV and 481 women without HIV, WLHIV were significantly less likely to receive appropriate Pap smears (56.1% vs. 74.2%, p < 0.001), mammographies (57.1% vs. 88.4%, p < 0.001), and at least one dose of the HPV vaccine (7.1% vs. 20.0%, p = 0.002). Survey data from 41 WLHIV revealed that being sexually active, heterosexual, in a relationship, premenopausal, and housing secure were associated with higher Pap smear adherence. These findings underscore the importance of addressing both individual and systemic factors to improve the provision and receipt of women's preventive health services WLHIV, especially in rural healthcare settings.