Astra Apartments and Suites, Imerovigli, Santorini $$$$
Concierge.com's insider take:
You can still top out at over a grand for one of the new private-pool suites at this Santorini cliff-hanger, which is split into 16 traditional-style apartments and 12 eclectic suites. But price being a relative thing, it just may be the most undervalued place to stay on the island. The decor is art-hotel chic. (The red bathroom in one of the Jacuzzi suites registers at just below over-the-top.) The caldera views, from poolside or private patios, are better even than those from Oia. Manager George Karayiannis is always so cheerfully ready to deal with any request (You need to borrow a laptop for your stay? No problem, no charge), you almost wonder if he is really Greek. For some, the only drawback here are the steps, which are numerous even by Santorini standards. A few trips up and down them should add greatly to even the most fit guest's appreciation of the hotel's new restaurant.
Closed November through March.