Objectives The purpose of this study was to describe the services provided by community pharmacists and their confidence in providing advice on self-medication for women during pregnancy and breastfeeding. Methods A cross-sectional, questionnaire-based study was distributed online to community pharmacists across Jordan in the period from August through December 2020. The questionnaire identified the services most frequently offered to women throughout pregnancy or breastfeeding and evaluated the community pharmacists’ confidence in providing advice on self-medication and other services for this population group. Key findings A total of 340 community pharmacists completed the questionnaire. Most of them were female (89.4%), and just over half (55%) had less than 5 years of experience. The services offered by community pharmacists to women throughout pregnancy were dispensing medicine (49.1%), and dispensing herbal products (48.5%), whereas the services mainly provided for women during breastfeeding were providing advice on contraception (71.5%), and dispensing medication (45.3%).The most frequent complaints reported by women during pregnancy were gastrointestinal and urinary symptoms, and for women during lactation low milk supply and contraception. Regarding pharmacists’ confidence in providing advice on self-medication, nearly half of the respondents (50% and 49.7%) reported that they had confidence in solving medication and health challenges during pregnancy and breastfeeding, respectively. Conclusion Although community pharmacists provided different services for women who were pregnant or breastfeeding, many did not feel confident handling them. Continuous training programs are required to enhance community pharmacists’ ability to provide adequate care for women during pregnancy and breastfeeding.