76 Main on Nantucket, Massachusetts
While Nantucket is a popular summer destination, it’s just as lovely in the quieter off-season when the town gets decked out in lights for the holidays. Stay in the heart of town at this 20-guestroom hotel recently renovated in a crisp, modern, New England style. For the holidays, guests receive a locally made stocking stuffer gift as part of their stay. And if you’re in town the weekend of December 6, enjoy the 40th annual winter stroll weekend, featuring a Christmas market, Santa’s arrival by boat, a magical talking tree, entertainment, and more. Doubles from $139/night. 76main.com