1864 The Sea Captain's House, Oia, Santorini $$$$
Concierge.com's insider take:
The Kapetanospito (meaning sea captain's house in Greek), built by the ship-owning Sigouras Sarris family, is as old as the Greek constitution and is one of a very few historic-preservation houses in Oia. By village standards, this is a very grand place, with its double-terraced front with false pillars of volcanic red rock, courtyard, and wide-plank floors; yet it's also typically Santorinian, with high vaulted ceilings and an interior partially carved into the cliffs. The hotel is split into two villas and three suites; although it's possible to rent the whole place to yourself. All the rooms have canopy beds and are crammed with antiques and local artwork. For those who prefer staying on the grid, this place is ideal: There's satellite TV, DVD and CD players, Wi-Fi, voice mail, AC—everything, that is, except a pool. But there are Jacuzzis in all three suites, and the village beach is only a ten-minute walk away. There's also an epic breakfast and a ten-percent discount at two of the best local restaurants, Ambrosia and Ambrosia & Nectar, because the hotel owners own them, too. You can also opt for über–room service on your suite's rooftop terrace. For those interested in some pampering, there's also an on-site Caldera Massage Studio.
Closed December to February.