Dundee Ready Education Environment Measure (DREEM) inventory has been exhaustively used to evaluate the education environment (EE), especially in the health sector to identify the strengths and weaknesses of the program. This study was designed to investigate the medical students’ perceptions about the education environment (EE) of the College of Medicine (COM), Jeddah. This cross-sectional study was carried out on medical students and conducted between May and August 2020. A predesigned DREEM questionnaire written in English containing five subdomains was adopted to achieve the purpose of the study. A total of 220 students responded to the dispensed survey with a mean age of 21.97 (SD = 1.28). Male and female students represented 64.5% and 35.5% of the respondents, respectively, while most of them were in the fourth year of medical college (109, 49.5%), and the majority belonged to phase II (basic sciences) of the college (144, 65.4%). The overall total DREEM score for EE was 129.64 (SD = 31.81; 64.82%), and all the five subdomains of DREEM scored above 60% with the highest score by students’ academic self-perception (SASP) (21.22; 66.31%) and the lowest by students’ perception of learning (SPL) (30.16; 62.83%). Also, SASP2 was the highest scoring item with a mean of 3.13 (SD = 0.96), while SPA8 was the lowest with a mean score of 1.99 (SD = 1.38). We also compared our study with the available literature for contextual interpretations. The students’ assessment for EE of the medical program was positive; however, we identified a need for an improvement plan for six-weak scoring areas and one of the weak domains of DREEM i.e., students’ perception of teaching (SPT).