Where to stay in Santorini is the first real decision of a wine trip to the island, and it is less obvious than the postcards suggest. The famous sunset villages of Oia, Fira and Imerovigli hang on the caldera rim, while most of the cellars sit inland, among the low basket-trained vines of Pyrgos, Megalochori and Episkopi Gonia. These six hotels cover both sides of that trade.
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In this article
How we chose where to stay in Santorini
Three rules cut the field. Every hotel is bookable on Expedia, so you can check dates through the links below and read the same verified guest reviews we read. Every hotel scores at least 9 out of 10 from real Expedia guests, with dozens of reviews behind the score. And together they cover both halves of the island: the caldera villages for the view, the wine villages for the cellars, with a wine program or a cellar restaurant where a hotel has one.
We grouped the six by village rather than ranking them, because on Santorini the village decides the trip. Oia gives you the sunset and the longest drive to the vineyards; Pyrgos and Megalochori give you the vineyards and a quieter evening. If you are still deciding which cellars to visit, our guide to Santorini wineries explains how the island’s wine areas differ.
Oia, at the northern tip
Oia is the village on every Santorini poster: white houses and blue domes stacked on the cliff, and crowds at the castle at sundown. It is also the farthest point from the southern vineyard belt, so a stay here means driving to your tastings and coming back for the view.
1. Canaves Oia Suites, Small Luxury Hotels of the World
Canaves is the splurge in this list, and the reason is privacy. In a village where the lanes fill with day-trippers by late afternoon, its suites and villas step down the cliff below the crowds, and many of the suites come with their own plunge pool facing the caldera, so the island’s busiest hour passes somewhere above you.
It suits a couple who want Oia without Oia’s noise, and who are happy to make the vineyards a day trip rather than the base. The limit is the drive: the cellars of Pyrgos and Megalochori are at the other end of the island, so plan one winery day with a driver and keep the evenings for the cliff.
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2. Andronis Boutique Hotel
Andronis Boutique Hotel is the Oia choice for travelers who want the view at its most direct. The terraces sit right on the edge of the cliff, the rooms look straight out over the caldera, and the guest scores on Expedia are about as close to perfect as hotel reviews get.
It is a hotel for slow mornings and long sunsets, not for an early start to the wineries, and the steps that come with any cliffside address in Oia are part of the deal. Pair it with a booked tasting day in the south, then come back for dinner on the terrace while the caldera turns orange.
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Fira and Imerovigli, on the caldera rim
Fira is the island’s main town and its transport hub, with buses, taxis and car rental desks close at hand. Imerovigli, a short walk north along the rim, sits high above the water and is noticeably calmer. Both sit in the middle of the island, which makes them the practical compromise between sunset and vineyards.
3. Aigialos Luxury Traditional Settlement
Aigialos earns its place as the best value on the caldera rim. It is a cluster of traditional houses restored as one small hotel on the cliff edge in Fira, so you get the classic Santorini setting, whitewashed walls and a pool facing the volcano, at a rate well below the Oia hotels.
The trade is the town around it: Fira is lively at night and busy with cruise passengers by day, so this is for travelers who like having restaurants and bars at the door. From the middle of the island the southern cellars are an easy drive, which makes it a sensible base for a trip with a tasting every day.
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4. Grace Hotel, Auberge Collection
Grace is the most wine-minded of the caldera hotels. Its Expedia listing includes a tasting room, private wine tours and wine release events, so the island’s Assyrtiko comes to you as well as the other way around. The infinity pool faces Skaros Rock, the old fortress headland of Imerovigli, which is one of the most photographed views on the island for good reason.
It is a hotel for couples who want a caldera address with a quieter evening than Oia or Fira, and who will use the wine program rather than ignore it. Rates sit near the top of this list. Imerovigli is close to Fira for transport, and the southern cellars are a straightforward drive away.
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Book it
Caldera rooms go first
The caldera hotels have few rooms and long waiting lists for spring and early fall. If your dates are fixed, compare the whole island on the same dates before you settle on a village.
Pyrgos and Megalochori, the wine villages
Inland and to the south, the island changes. The vines grow low to the ground, coiled into baskets called kouloura that protect the grapes from the wind, and the villages are working places rather than viewpoints. Pyrgos is home to Santo Wines, and Estate Argyros is just south in Episkopi Gonia. This is where to stay in Santorini if the wine is the reason for the trip.
5. Zannos Melathron
Zannos Melathron is the way to sleep in Pyrgos itself, the old hilltop village at the center of the island. The hotel stands in the heart of the village and its pool looks north across the island to the Fira ridge, so you trade the caldera at your feet for a wide view of it, and a far quieter evening.
It suits travelers who want to walk to dinner in a real village and reach the cellars in minutes rather than half an hour. The limits are a smaller review count than at the caldera hotels and a shorter list of facilities. For a wine week, though, the address is hard to beat.
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6. Vedema, a Luxury Collection Resort
Vedema is the wine lover’s resort of Santorini. It sits in Megalochori, a village in the heart of the southern vineyards, and its most memorable room is the Secret Wine Cave, a restaurant under a stone vault where dinner comes with the island’s wines. Some of the rooms have their own private hot tub.
It is for travelers who would rather wake up among the vineyards than above the caldera, and who want a full resort around them, spa and all. Expedia showed no rooms for our test dates, so check your own dates early. Venetsanos Winery is close by, and the resort’s own site lists its current dining and wine programs.
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When to book a Santorini hotel
Santorini works on a short season. Late spring and early fall are the sweet spots for a wine trip: the cellars are open, the heat is manageable and the caldera is less crowded than in July and August. The harvest on the island usually starts in mid-August, earlier than on the mainland, so a late-summer trip can include the first days of picking.
Book early for any caldera address. The hotels in Oia and Imerovigli are small, and the rooms with a private pool are the first to go for May, June and September. The wine villages are more forgiving, but the best rooms in Pyrgos and Megalochori still fill weeks ahead in high season.
Getting there
Santorini has its own airport, with seasonal flights from Athens and many European cities, and the main ferry port at Athinios sits below Megalochori on the caldera side. Once you arrive, the bus network is built around Fira, and taxis are limited at peak times. For a wine trip a rental car is the practical choice, as long as one person stays off the tasting glass: our guide to renting a car for a wine trip in Europe covers insurance, documents and drink-driving rules.
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The roads are narrow and parking in Oia and Fira is scarce, which is one more argument for the inland villages. If you would rather not drive at all, book a guided tasting day and let the driver handle the island; the Santorini wineries guide explains which cellars to put on the list.
Choosing between them
The choice comes down to how much of the trip you want to spend looking at the caldera. For the full postcard, Canaves and Andronis in Oia are the two to compare, with Canaves winning on privacy and Andronis on the directness of the view. For a central base, Aigialos is the value pick in Fira and Grace the wine-minded splurge in Imerovigli.
If the wine is the point, stay in the villages. Zannos Melathron puts you in Pyrgos for the price of an ordinary caldera room, and Vedema gives you a full resort with a wine cave under the same roof. Santorini is not the only volcanic island where the choice works this way: our guide to where to stay in Taormina weighs the same view-versus-vineyards trade on Mount Etna.
Prices are “from” rates, indicative and set by our booking partners: they change with dates and availability, so check the current rate on Expedia.
