Sleep Inside a Cave
If the term "boutique cave hotel" sounds like an oxymoron, suspend your disbelief for a moment. Cave hotels are a thing in Greece, and some of the most memorable accommodations in the country are built right into the coastal topography. Santorini has several, including the Iconic Santorini. Carved from the wall of a caldera (a large volcanic crater) in the village of Imerovigli, the hotel offers curved guest rooms—their shape follows the natural lines of the caves—with beautiful views over the Aegean Sea.
Nearby, close to the village of Oia, Aris Caves was built on and around a cluster of ancient cave dwellings. The archaeological site was transformed into a modern hotel with apartment-style accommodations: each unit has a kitchenette or a kitchen and private terrace, and many feature outdoor Jacuzzis. The views of the sea, Nea Kameni volcano, and the island of Thirasia is stunning, to say the least. Note that the extensive staircases and low walls make the hotel not recommended for children or travelers with limited mobility.
Check Into a Castle
You'll get the royal treatment when you arrange a stay at one of Greece's stately castle hotels. Just a mile from the lovely beach town of Diros is Arapakis Castle, a 200-year-old fortress surrounded by a peaceful olive grove. Though the castle has since been turned into a contemporary hotel, you'll still see its original towers, mill, and oil press, and guest rooms have thick stone walls and wood-beamed ceilings that remind you of the building's history.
In Kardamyli—a seaside town located a short drive south of Kalamata—Kastro-Zoi offers lodging inside a 12th-century medieval castle. Naturally, the plumbing has been updated, but the wood and stone interiors and guest rooms with cast-iron beds and classic Greek paintings offer plenty of historic charm.
Chat with a local specialist who can help organize your trip.
Wine, Dine, and Recline at a Vineyard Hotel
Greece has several distinct wine-growing regions producing delicious varietals, and there's no better way to sample them than staying at a winery or vineyard hotel. At one of three luxury residences at Scalani Hills Boutari Winery near Heraklion on the island of Crete, you'll wake up on the edge of the vineyard—and you'll have a private veranda where you can sip Chardonnay to your heart's content.
At Stella Vineyard, in the foothills of Mount Aenos on the island of Kefalonia, studio apartment-style accommodations feature privileged clifftop views of the mountains, Lourdas Bay, and of course, the vineyards below. The local specialty is a Greek red wine called Mavrodafni: it's the perfect wine to linger over while enjoying the peace and quiet.
Spend the Night in a Windmill
If a castle or a cave isn't quite unforgettable enough for the Greek adventure you're planning, how about sleeping in a windmill? All over the Cycladic Islands, windmills were built to aid in the production of flour. Some have been turned into private residences or hotels, like the Windmill Edge Villa. Built in the 1750s, the windmill is located on the edge of the caldera cliff in Imerovigli. Today, the villa is a one-of-kind lodging option: you'll have three round floors to yourself, each with panoramic views of the sea and the cliffs.
Another option is the white-washed Windmill Hotel, located on a hilltop on the island of Kimolos. It's simple and rustic inside, featuring just two rooms with wooden furnishings, built-in sofas, and views of the sea from multiple terraces. There are historic mid-19th-century outbuildings, too, housing a few more guest rooms. Scattered across the islands, there's a range of other windmill hotels; all are quiet and unique, ideal for a relaxing holiday.
Live Like a Local in the Ancient City of Athens
Your accommodations in Athens might not be at the top of your travel-planning list (many travelers to Greece are thinking first and foremost about islands, beaches, and cliffs), but a stay in the Greek capital can be enchanting if you do it like a local. Instead of a traditional hotel, consider renting an apartment; not only will you enjoy extra space (great for jet lag recovery after a long flight), but you'll also get a taste of what living in Athens is like.
Whether you choose a loft in the old city or a modern apartment with a stunning view of the Akropolis, an apartment rental is a solid value and a great cultural experience.