Flanked by the Atlantic on one side and Nantucket Bay on the other, this 1875 inn of 32 rooms feels like a private island—Great Point Wildlife Sanctuary forms its third border. Guests retrieve beach chairs from beneath Pratesi-dressed beds, dine at Topper's (reachable by the hotel's own boat), and explore dunes in a vintage Woody wagon. Adults only; nine miles from town, worlds from anywhere.
Eleven shingled cottages spread across a waterfront property with a private beach overlooking Nantucket Harbor, yet shops and restaurants lie just five minutes on foot. The intimate scale suits couples seeking seclusion or families with older children—loft sleeping areas reached by ladder add a sense of adventure. A polished retreat that balances island escapism with easy access to town.
Commanding a prime harborfront position with direct water views, this 66-room property spreads across a main building, eleven shingled cottages, and two downtown lofts—some featuring gas fireplaces and private decks. A fleet of Hinckley yachts awaits at the private dock for coastal excursions, while Brant Point Grill draws locals with its seafood and signature lobster Bloody Mary. The harbor-facing spa completes a quintessentially Nantucket experience.
Three 17th-century-style houses near Brant Point shelter this 18-room boutique property, where agricultural motifs replace the expected maritime clichés in a contemporary-classic design. Lawn space unfolds with firepits and games, while an indoor/outdoor lounge serves complimentary breakfast. A pool arrives in the barn for 2025. Pet-friendly and minutes from the harbor, it suits travelers seeking polished informality over Nantucket's familiar nautical tropes.
A former sea captain's residence converted into a 20-room boutique property, 76 Main sits directly on Nantucket's principal thoroughfare with shops, restaurants, and island attractions immediately accessible on foot. The intimate scale preserves a residential atmosphere, while complimentary amenities add practical value. Families with children find an easy welcome here, making it suitable for multi-generational island escapes.
Dating from 1847, this intimate seventeen-room inn on North Water Street preserves the architectural character of Nantucket's historic district while offering thoroughly modernized comforts. The daily rhythm includes complimentary breakfast and afternoon tea, rituals that anchor the guest experience. Families find particular appeal here, with several rooms configured for three or four guests and equipment available for young children.
Built for a prosperous whaling merchant in the nineteenth century, this 42-room inn retains its period character through antique furnishings and architectural details that evoke Nantucket's seafaring heyday. The main house holds thirty rooms while the adjacent Daniel Webster House adds twelve more, all within walking distance of the island's cobblestoned center. Families receive colouring kits at check-in, making it a relaxed choice for multigenerational stays.
Families gravitate toward The Beachside at Nantucket for its proximity to Children's Beach and a heated pool that keeps younger guests entertained between excursions. The North Beach Street address places restaurants and boutiques within easy walking distance, while room rates remain notably accessible for the island—a practical base that delivers solid value without sacrificing convenience.
Roman & Williams transformed a 19th-century sea captain's house into this 20-room boutique retreat on Broad Street, crafting interiors that channel maritime heritage without succumbing to whaling-village kitsch. The design details reward close attention—weathered woods, brass fixtures, textured fabrics. Downstairs, Via Mare brings Venetian small plates courtesy of chef Marcus Gleadow-Ware, whose résumé includes a Michelin-starred New York kitchen.
A flamboyant Victorian on understated Broad Street, this 27-room inn underwent meticulous restoration—plasterwork mixed to original 19th-century recipes—before Rachel Reider layered her modernist interiors over the period bones. Maritime touches nod to the island setting, while steam rooms and on-request spa treatments offer quiet indulgence. Complimentary bikes make the downtown location a practical base for exploring Nantucket's cobblestone lanes.
Overlooking Nantucket Bay from The Wauwinet's remote eastern shore, Topper's sources oysters and quahog clams directly from its own waters for a genuine dock-to-table experience. Chef Kyle Zachary's seven-course tasting menu might feature Hudson Valley foie gras with butternut squash, while the heated waterfront deck serves a more relaxed roster of raw bar selections and lobster rolls. A 1,450-label wine list and complimentary boat transfer from town complete the draw.
The island's high season runs from Memorial Day through Labor Day, when all restaurants and hotels operate at full capacity and ferries run frequently. September offers warm days, thinner crowds, and the celebrated Nantucket Wine Festival. Stroll and Christmas Stroll in late November and early December draw visitors for holiday shopping along candlelit streets, though many properties close from January through April.
The Steamship Authority operates year-round ferries from Hyannis, with the fast ferry taking one hour and the traditional boat about two hours and fifteen minutes. Hy-Line Cruises runs seasonal high-speed service. Cape Air, JetBlue, and United offer direct flights to Nantucket Memorial Airport from Boston, New York, and other northeastern cities, with flight times under an hour from most hubs.
Siasconset — known locally as 'Sconset — sits seven miles east, a village of rose-covered cottages perched above the Atlantic with its own small café scene. Madaket, at the island's western tip, offers dramatic sunsets over the ocean. Surfside and Cisco provide excellent beaches accessible by bike path from town, while Wauwinet on the northern shore combines harbor and ocean beaches with protected conservation land.
Thirty miles off Cape Cod, this crescent-shaped island preserves its whaling-era architecture with unusual devotion. The town's cobblestone Main Street, lined with federal-style mansions built by nineteenth-century ship captains, leads down to wharves where ferries from Hyannis now dock. Grey-shingled cottages weathered by salt air define the island's aesthetic — a look so distinctive that local building codes mandate it.
The accommodation scene clusters around two poles: the compact downtown centered on Easy Street and Broad Street, where converted sea captains' homes operate as intimate inns, and the beach communities of Siasconset on the eastern bluff and Madaket to the west. Summer brings Boston and New York families who've returned for generations, filling the same properties their grandparents favored. The dining scene punches above its weight for an island of eight thousand year-round residents, with raw bars and farm-to-table kitchens concentrated along the harbor.
