Nantucket's grandest luxury hotel is also one of the most private and remote on the island, set along a stunning stretch of northeastern coast. The opulence here is low-key, but it's still upscale. Though you'll see plenty of guests sauntering around in sarongs and flip-flops, they're likely headed to the on-site Spa by the Sea for a body scrub or to settle into one of the many cushy chaises scattered through the blooming gardens and along the private beach (where staffers scurry over with fresh towels and cold drinks).
The sprawling main building houses 28 guest rooms—done up antique pine, wicker, and tasteful chintz, with Pratesi linen-clad beds and lace-curtained windows. There are also four freestanding cottages, whose cozy gas fireplaces and private sundecks make them popular with honeymooners. The hotel has a shuttle that makes the nine-mile trip to and from Nantucket Town almost hourly until 11 p.m., and the Wauwinet Lady boat service for guests who would like to take in the harbor. That said, you might be hard-pressed to drag yourself off the property.