Medical devices and contact assemblies for electrical connections between medical device components are disclosed herein. A medical device in accordance with a particular embodiment includes a patient implantable element having a receiving cavity and at least one contact assembly positioned in the receiving cavity. The contact assembly can include a housing having an annular shape with an inner surface defining at least in part an opening. The contact assembly can further include a contact disposed at least partially within the opening and having a plurality of leaf spring portions.