Not far from Cape Cod is the postcard-perfect island of Nantucket. There’s no shortage of luxury hotels here, and a classic choice is this harborside hotel that dates back to the 1920s – it has the authentic shingle-style exteriors to prove it. The property has grown over the years to include more hotel rooms, a separate inn, garden cottages and larger residences. All come with elegant furnishings, plush beds and Italian linens, while some have fireplaces. Sip a lobster bloody mary at Brant Point Grill, featuring seafood and steaks, or hit the cobbled streets for more restaurants and lively bars in the historic district. There’s also an on-site spa, featuring organic products.