Background: COVID-19 vaccination is recommended for older adults by the World Health Organization. However, by July 15, 2021, only 26% of individuals over 60 years old in Hong Kong had received a first dose of the vaccine. The health belief model and the theory of planned behavior have been used to understand the determinants for COVID-19 vaccination in past literature. However, vaccination determinants can be complex and involve social and cultural factors that cannot be explained by micro-individual factors alone; hence, the health belief model and the theory of planned behavior cannot provide a complete understanding of vaccine hesitancy. Few studies on the barriers to, hesitancy toward, and motivations for COVID-19 vaccination among older Chinese adults have been performed. The aim of this study is to fill this gap by conducting a comprehensive analysis of this subject using the critical medical anthropology framework, extending the health belief model and the theory of planned behavior in understanding vaccination determinants among the older adult population. Methods: Between November 2020 and February 2021, 31 adults (24 women and 7 men) over the age of 65 took part in semi-structured, one-on-one interviews. The data we gathered were then analyzed through a phenomenological approach. Results: Two major themes in the data were examined: barriers to vaccination and motivations for vaccination. The participants’ perceptions of and hesitancy toward vaccination demonstrated a confluence of factors at the individual (trust, confidence, and social support networks), microsocial (stigma toward health care workers), intermediate-social (government), and macrosocial (cultural stereotypes, civic and collective responsibility, and economic considerations) levels according to the critical medical anthropology framework. Conclusions: The decision to receive a COVID-19 vaccination is a complex consideration for older adults of low socioeconomic status in Hong Kong. Using the critical medical anthropology framework, the decision-making experience is a reflection of the interaction of factors at different layers of social levels. The findings of this study extend the health belief model and the theory of planned behavior regarding the understanding of vaccination perceptions and relevant behaviors in an older adult population.