Background: The COVID-19 pandemic has strongly impacted on healthcare services’ organization and healthcare workers’ mental health, increasing the risk of psychological symptoms and burnout. Italy has been one of the most affected countries, especially the northern regions, even with exceptions in some rural provinces. Aim: We chose to investigate the mental health conditions of healthcare workers operating in the rural province of Rovigo (a small town in Veneto, northern Italy), where relatively few deaths and contagions were reported during the pandemic, even if Veneto—globally—was one of the most affected regions of Italy. We wanted to verify the psychological outcomes of health workers operating in a context where the impact of the pandemic appeared to be relatively mild. Methods: Through an online survey, we investigated perceived difficulties at work and in daily life, perceived loneliness and social support, coping strategies, and level of psychological distress (sample size: 749; mean age = 48.04 years, SD = 10.66). The questionnaire had both open- (2) and close-ended questions (5 single-choice and 13 multiple-choice). We verified possible associations between sex, age group, work department and percentage of responses with chi-square tests of independence on each question. Data cleaning excluded all contradictory answers from the multiple-choice questions from the analyses (final sample size: 640). Results: Frontliners and non-frontliners reported a similar experience of the COVID-19 pandemic (without significant differences in perceived difficulties, coping strategies and sources of support). Nevertheless, they still reported various forms of negative emotions (e.g., helplessness—40.94%; sadness—36.56%; frustration—32.66%) and lack of support from the health organization (especially frontliners—28.72%). However, psychological help was scarcely requested. Conclusions: Despite the province not being massively affected by the pandemic, healthcare workers felt the need for clearer and more supportive guidance. They seem to perceive collective opportunities to share needs and difficulties as more useful than individual interventions (as those provided by the ad hoc created listening service).