To the OP (staying out of the BW pricing discussion): We have the same dilemma in our upcoming mid-November trip. AA changed schedules and is now landing us at STT around 8:30 PM. I looked at the BW and Windward Passage options, but found Bunker Hill Hotel to be best priced for a one night stay. Basic room, about $90. Fine with us, since all we do is arrive, sleep, then catch the next morning's ferry. There are other small hotel options like that in CA. The BW places and WP seemed to be in the mid-100 range or up, after you add in taxes.

Rob