Guest House Pitsinades, Pitsinades, Kythera $$$$
Concierge.com's insider take:
Kythira is farther south than the other islands in this group and is easily overlooked by many travelers—but it shouldn't be. Windswept, dotted with whitewashed houses, and surrounded by stunning views, the island has an unspoiled, slightly desolate feel that has led to rumors of its being haunted. Nowhere is that stark beauty more evident than in the car-free medieval village of Pitsinades, home to this restored 150-year-old house. Its six unique rooms are decorated with vaulted arches, stone mosaics, and blue-and-white pottery; the quiet patio is a perfect place to watch the sun set or have your first cup of coffee (homemade marmalade is served with breakfast every morning). After breakfast, guests often wander among the neighboring villages or take a 20-minute drive to the harbor and pebble beaches of Agia Pelagia.
Closed mid-September through mid-June.