A compactable vaginal pessary for managing pelvic organ prolapse is provided. The compactable pessary easily expands once inside a patient's vagina, remaining firmly anchored in the vaginal cavity during movement, thereby effectively countering the effects of any prolapsing organ. In a first embodiment, the vaginal pessary employs an expandable and collapsible frame member, while in a second embodiment; the frame member is an open, substantially cone-shaped, collapsible frame member that is biased to an open position. In a third embodiment, the compactable vaginal pessary is a yieldably extensible, self-retracting pessary. The vaginal pessary of the present invention may be easily inserted and removed by a patient on a daily basis, or as needed, thereby facilitating good hygiene and thus reducing or eliminating common pessary related complications.