Getting to Nantucket Island - Since it's roughly an 8-hour drive from Manhattan, I would opt for a direct flight which will take only an hour. When booking a place to stay, I would suggest the Historic Nantucket Hotel, Jared Coffin House or the iconic, White Elephant, which boasts harbor views.
Greydon House, 20-room luxury hotel on Nantucket island (17 Broad Street), designed by Roman and Williams in collaboration with architect Matthew MacEachern of Emeritus. The original structure (on the right) dates to the 1850s. Via Habitually Chic (12 October 2016).