Castello di Vicarello, Poggi del Sasso $$$$
Concierge.com's insider take:
Near the village of Sasso d'Ombrone, 40 minutes' drive northeast of Grosseto, Vicarello is a 12th-century feudal castle perched on a rocky spur with views west to the sea. The atmosphere is that of a discreet house party, presided over by charming hosts Aurora and Carlo Baccheschi Berti. Aurora lived in Bali for 18 years, something that comes through in the five suites—three in the castle itself, two more in the grounds—which mix Indonesian furniture with contemporary rural art. There are two swimming pools—which means that much of the time guests have one to themselves. Lavender, rosemary, and a whole bank of ground roses cover the slopes just below the castle, with terraces of olives and vines down below. Suites have real working fireplaces (it can get quite chilly here out of season), and breakfast—much of it based on produce made, grown, and/or baked by the hosts—is served in a huge country kitchen. Signora Baccheschi Berti also organizes impromptu cooking courses for those who want to do more than just go for long walks or lounge around the pool.