Best of Boston

Opened in 2018, this Nantucket newcomer first charmed us with its well-designed guest rooms, complete with local artwork, smart pops of color, and beds dressed with Fall River–made Matouk linens. But Hotel Pippa, the brainchild of longtime islanders Christopher and Asta Skehel, is much more than a pretty face: Set on the cobblestones of downtown Chestnut Street, it’s also an undeniably lush home base for a weekend spent exploring nearby restaurants, art galleries, and (of course) miles and miles of pristine beaches.