33 Best Hotels in Cape Cod, Massachusetts

Dating back to the 1920s, this storied resort has had many lives—as a speakeasy, a dance club (owned by broadcaster Barbara Walters's father), and a beach club owned by Boston Celtics coach Red Auerbach—but now, the year-round resort on a private stretch of Old Silver Beach is a happy place for vacationing families and couples. Thanks to recent renovations, guest rooms, cottages, and public areas are fresh and modern. They've also added a zone of eateries, so guests don't have to leave the property; options include pizza, takeout seafood, ice cream, and a fine dining restaurant, The Lantern Room. There's also a pool bar, but the real draw are lounge chairs and umbrellas lining the beach.

Outside, this 1895 sea captain's home looks like many other historic houses on the Cape; inside is a surprisingly upscale boutique B&B appointed with reclaimed barn wood, leather furnishings, and two gallery rooms filled with fine art photography. Innkeepers Adrian and Xenia D'Ambrosi have created an adults-only haven featuring beautiful plants (Xenia is a garden designer) and excellent four-course breakfasts (Adrian is a chef who has worked for Jean-Georges Vongerichten.)

With its graceful columns and welcoming front veranda, the regal Winstead Inn sits along a quiet street; many of the rooms have a view of the heated, outdoor saltwater pool, a real oasis with potted palms, fountains, and flowers. The inn has a second property 1½ miles away in Harwich Port, with 14 rooms on a private stretch of beach fronting Nantucket Sound. Inn guests have use of the beach amenities.