7 Best Hotels in Nantucket, Massachusetts

This resplendently updated 1875 resort straddles a "haulover" poised between ocean and bay (think beaches on both sides); it features cushy country-chic guest rooms (lavish with Pratesi linens) and a fine-dining restaurant, Topper's. Guests can take advantage of activities like sailing, launches to a private beach, and driving tours of the Great Point nature preserve. A slew of complimentary perks, from the use of bicycles, paddleboards, and kayaks to afternoon port and cheese, are nice touches.

The original impressive 19th-century shell remains, though its interior is sleek, gleaming, and crisp, with a blend of calming neutrals and navy. Choose a standard room or from one-, two-, and three-bedroom suites, all with thoughtful personal touches and decorative nods to history: sperm whale-decorated pillows on the beds, historic photographs and murals of Nantucket, children's books placed in each room. Service here is exceptional, friendly, and plentiful, as are the amenities.

Ken Withrow worked in the hotel business, Deborah Withrow in high-end retail display, and guests get the best of both worlds in this 1770 house, a stone's throw from the bustle of Main Street. Amenities include Frette and Matouk linens, plump duvets, and lush robes, as well as a full gourmet breakfast served on the tree-shaded garden patio—or in bed.

This reimagined and refreshed circa-1883 sea captain's home in the heart of Nantucket has a literary bent with rooms that celebrate Nantucket notables like writers Elin Hilderbrand and Nathaniel Philbrick. Rooms are done up in fresh, beach-y blues, with some in the main house and some in a building behind the patio. Among other niceties, they offer a BYOB mixer bar in the afternoon and rides to the ferry and beach in the house Jeep.

The largest house in town when it was built in 1845, this three-story brick manse is still plenty impressive, and the property is actually comprised of two buildings, the Main House (closed off-season) and the Jared Coffin House. Antiques-filled parlors are a study in timeless good taste, and the guest rooms, which vary greatly in size and grandeur, are decorated in a low-key, traditional style.

Located atop a hill on a quiet street about ten minutes from town, this old Victorian sea captain's home has a grandma's house-gone-trendy feel. Part of the Life House hotel chain, the inn offers 14 eclectically appointed rooms on three floors; the third-floor "cozy" rooms have slanted ceilings. Niceties include Le Labo bath products, a daily cocktail hour, and complimentary s'mores fixings for enjoying around the firepit.

This 1831 home exudes history: it was built for whaling captain Obed Starbuck on the site of the birthplace of abolitionist Lucretia Mott. Guest rooms, named for the ships Starbuck commanded, are furnished with period antiques and pretty wallpaper, and the basement restaurant of the same name (delighted murmurings waft up) generates a wonderful continental breakfast and afternoon tea.