This study examines challenges experienced during COVID-19 vaccination efforts, facilitating factors that increased vaccination, and lessons learned from healthcare providers and housing program staff who delivered healthcare and services to Veterans experiencing homelessness during the SARS-CoV-2 pandemic. Qualitative, semi-structured interviews were conducted with seven transitional housing program staff in northern California, southern California, Florida, Iowa, Kentucky, Massachusetts, and New Jersey (January-April 2021) and six primary care providers serving Veterans experiencing homelessness, four from clinics in California and two from a clinic in North Dakota (July-August 2021). Interviews were transcribed and analyzed using a rapid analysis approach. COVID-19 vaccination rates were between 40 and 60% among Veterans who received care from the primary care providers and between 20 and 90% among Veterans who were enrolled in the transitional housing programs. Barriers that providers and housing staff encountered when getting Veterans vaccinated for COVID-19 included lack of eligibility, the vaccine appointment scheduling process, transportation and communication challenges, Veterans’ distrust in the government, vaccine mandates, and vaccine hesitancy among organization staff. Recommendations to increase COVID-19 vaccine uptake included making vaccination more convenient, using trusted sources such as homeless program staff or Veteran peers to provide educational information about the safety and efficacy of COVID-19 vaccines, and encouraging rather than mandating vaccination. These lessons will enable entities providing care to people experiencing homelessness to develop more effective policies and educational campaigns to improve vaccine acceptance and uptake among this vulnerable population.