Background: The negative psychological impact of COVID-19 in the general population has been well documented. Similar studies among those who were infected and who underwent quarantine remain scarce, particularly in the Arab region. The present study aims to fill this gap. Methods: In this cross-sectional study, suspected/confirmed COVID-19 individuals who were quarantined in the Ministry of Health (MOH) facilities were invited to participate in an online survey. All consenting participants answered a generalized questionnaire that included demographic characteristics, as well as a five-part questionnaire that assessed the symptoms of depression, anxiety, insomnia, and distress. Results: A total of 335 suspected/confirmed COVID-19 individuals (198 males and 137 females) participated. Being female is associated with increased risk of depression (odds ratio OR 1.8 (confidence interval, CI 1.1–3.1; p = 0.03)) as well as being employed by the government (OR 2.8 (CI 1.1–7.0; p = 0.03)). Level of education (OR 2.3 (CI 1.0–5.4; p = 0.049)) and employment in government (OR 3.0 (CI 1.2–7.8; p = 0.02)) were significantly associated with distress. Increasing age (45 years and above) appeared to be protective against distress (OR 0.2 (CI 0.02–0.69; p = 0.008)), as well anxiety and sleep pattern (OR 0.3 p < 0.05). Conclusion: Findings of the present study highlight that infected COVID-19 populations are at higher risk for acute and detrimental psychological well-being during quarantine and/or self-isolation. Identification of the coping mechanisms of older adults during periods of distress may prove beneficial in the pandemic preparedness of younger generations.