We have stayed many times at windward passage if arriving late knowingly..or delayed. It's across street from ferry dock and close to many pretty good eateries.

These days we are going/coming to Virgin Gorda. If we have a flight landing in STT before 4pm we always try to make the ferry. Going home we always select an afternoon flight, usually after 3 pm..we never go to STT the night before and have never missed a flight. I have never heard of Windward Passage turning away anyone being full but suppose could happen during spring break etc.