Background: Surgical resection of vestibular schwannomas (VS) can be responsible for single-sided deafness (SSD). Hearing restoration can be a challenge both for the otolaryngologist and the patient. Patients and Methods: In a retrospective series, we analyzed the charts of SSD patients operated on for VS from 2005–2021, checking which type of hearing rehabilitation was chosen. All patients who wanted a hearing restoration underwent a hearing in noise test (HINT) in a stereo auditorium with and without a bone-anchored hearing device (BAHD) worn with a headband on the deaf side. Then, they had a preimplantation one-month trial with the BAHD at home vs. contralateral routing of signal (CROS) or BiCROS (with contralateral signal amplification) hearing aids (HAs). Results: Among 52 charts of the included adult SSD patients, only 29 (56%) eventually chose a hearing rehabilitation device (14 BAHD). Only one BAHD patient required a device explantation for skin complications, but then asked for reimplantation. Another one swapped the BAHD for HAs 2.5 years after. Two patients only occasionally used their BAHD with a headband. Nine patients preferred HAs, mainly BiCROS. Their contralateral hearing was significantly less than BAHD patients (p < 0.05), and only three used their HAs every day. Conclusions: Hearing rehabilitation in SSD patients after VS surgical resection is chosen in about 50% of cases. In complement of HINT, a real-life comparative hearing trial helps patients chose the best device, with good long-term results when a BAHD is chosen. HAs are preferred when contralateral hearing is altered but are not always worn.