There are a number of places to stay on Nantucket. As you might imagine for a resort island, even in the early off-season your wallet will be thumped for the cost of a bed. White clapboard and blue hydrangeas ain't free.
The hotel I am personally fond of for inane reasons (eggs benedict in the middle of winter before a trip to the bookstore) is the Jared Coffin House. Old, brick, at the head of Centre and Broad streets, walking distance to anything in town.
The Languedoc has tasty fattening french food, lobster bisque swimming in cream, and a lovely downstairs (cheaper) cafe with cheerful gingham table cloths and the same stuff as upstairs. Apparently they also rent rooms. Worth a look. Kitty corner from the bookstore, Book Works. (Serious readers, head to Mitchells, on the corner of Orange and Main Streets).
If you are looking for a high-end hotel to brag about to future safari partners, head to the Wauwinet and light a small fire of bills in your grate. Lovely harbor views, of course, and the most expensive appetizer on the planet.
The Woodbox is old, dark-wooded and charming. They used to have a breakfast worth the summer rush, I don't know if that still holds true, but there's breakfast to go with the bed I am sure.
The Beachside is relatively affordable for Nantucket. It's walking distance from town, and very near Brant Point, which is as sweet (and small) a light house as you'll ever see.
The Ship's Inn looks nice, and Fair Street is a pretty old street.
House of Seven Gables has a memorable name. And you can throw your portuguese roll at one of those deer during breakfast.
By far the best deal on the island (which boasts not one motel) is the Nantucket Inn. Across from the airport, a few miles out of town (but not too far), your toes will not be massaged with walnut oil upon arrival, but you will get a bed and there is a pool.
This is a scattering of hotels on the island. Bed and breakfasts per square mile might exceed some national standard. Head to Yelp.com to look for more if none of these suit your fancy. I say if you can, avoid the White Elephant, the Harbor House, and the Wauwinet--they are all owned by a gentleman who owns much too much of the island and doesn't need your business. Support local. He owns the Jared Coffin House too--but let that be the only business we give him.
