Santorini in October: 3 Hotels I’d Book Now That Summer Prices Have Dropped
Santorini caldera at sunset with whitewashed cave hotels and lights along the cliff
If you have only seen Santorini in photos, August is usually what those photos cost: the cliffs, the crowds, and the rate on the cave room.
October is still that island. After sunset the caldera turns that deep blue you came for — the evening light, not the midday glare. The water is often still warm enough to swim. The streets are quieter. And the hotel bill is finally easier to look at.
I am not going to give you twenty hotels. These are the three I would book right now:
Katikies in Oia if the view from the room is the whole point
Dana Villas in Firostefani if you want the caldera without paying Oia prices
Xenones Filotera in Imerovigli if you want a quieter stretch of the rim — and, on the October dates I checked, a room that came in under $200 a night
You get the same kind of view. You just pay for it in a better month.
Each button below opens the October dates I already researched. The live price is there. Change the nights if your trip is a little different.
Why I keep telling people to look at October
Santorini does not trim a little in autumn. Prices drop.
A room that felt impossible in August often becomes realistic in October. It is still not a bargain island if you want the volcano in the window. It is simply no longer peak-summer punishment. Hotels along the mid-rim usually follow. Beach and village stays fall further, though most of those will not give you a caldera sunrise from bed.
A few cliff hotels start to wind down as autumn goes on, so compare a few nights and read the room type — not just the village name.
You will not book all three. Read until one feels like your trip, then open that button. That is the search I already set up for you.
If the view is the whole point: Katikies, Oia
Katikies Santorini in Oia with a cliffside terrace pool and caldera views across the Aegean
This is the most expensive stay on the page, and it should be. It is the Oia terrace version of October.
Katikies Santorini – Pelagos House sits on the cliff in the heart of Oia. You are a minute from the caldera, a short walk from the blue domes, and a little further from the castle. Three pools hang on the drop. Breakfast is included. At night you can have dinner over the same water you came to see.
Junior Suite is the room I opened — caldera side of Pelagos, village right there, volcano in front of you. In October, this is the version of Katikies I would actually book. In August I would think twice.
People who stayed in October still talk about the view and the breakfast. Others mention the staff and the pool terraces. The usual Oia warning still applies: there are a lot of steps. There is a lift, which helps, but it does not make the village flat. Parking and valet are on site, which is rare here.
Stay for the terrace. Walk the alleys after the day boats have left.
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This opens the October dates I checked. Look at the live rate there, then change the nights if you need to.
The caldera without Oia rates: Dana Villas, Firostefani
Dana Villas Cave Pool Suite in Firostefani with a private plunge pool and Santorini caldera views
If I wanted the caldera in October and did not want to pay Oia prices, I would start here.
Dana Villas & Infinity Suites sits at the quiet end of Firostefani, about a minute from the caldera edge. Fira and the Three Bells are a short walk. The volcano is in front of you. The sunset crush in Oia is not.
Deluxe Room is the one I would book. Private terrace, caldera, sea, sunset, breakfast included. On the October dates I checked, a few nights came in well below the summer rate and the view was still excellent.
Cave Pool Suite is the step up if you want water on your own terrace. It has a private rooftop plunge and a higher nightly rate. It is not the hotel’s shared infinity pool (that one is 16+ and still open in October), and it is not their larger Cave Pool Villa.
Guests liked the view, the staff, and the breakfast. Be ready for stairs — upper floors have no elevator. Some rooms are tight for big suitcases. There is no parking on the lot, though free off-site parking is available.
Pack light, double-check the room category, and you get the rim without the Oia bill.
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Both buttons open the October dates I checked. Compare the two rooms there. That is where the current prices are.
Under $200 on the dates I checked: Xenones Filotera, Imerovigli
Xenones Filotera terrace in Imerovigli at sunset with pool, sea views, and the Santorini caldera
Imerovigli sits on the high point between Fira and Oia. Skaros Rock is close. The walk toward Oia is about fifteen minutes from the hotel. You can go into Oia for sunset and still not sleep in the middle of it.
Xenones Filotera is the third stay I opened because the October rate was the surprise. Breakfast is included. There is a terrace, a restaurant, and a pool that stays open through autumn. Parking is on site. There is no elevator — two floors, like a lot of the rim. The airport is closer than it is from Oia.
Villa, Sea View (East Aegean) is the room on the search I saved. You still get the sea, just the other direction: morning light and open water, not the west caldera drop from the bed. That is how this rate exists. For the classic west light, you leave the room and walk — the path, Skaros, or the hotel terrace.
On the October dates I checked, this stay came in under $200 a night. That can change. The number that matters is the one on the button.
Guests come back for the view, breakfast, and staff, and because the hotel sits between Fira and Oia, near the bus and the trail. Several people said the same thing: you get the view without fighting for space the way you do in Oia.
Read the room category first. Then walk the path if you want the postcard from the other end of the rim.
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This opens the October dates I already looked at. Check the live rate while this room is still available.
Quick way to choose
Katikies, Oia — you want the postcard and you will pay for it
Dana Villas, Firostefani — you want the caldera cliff without Oia prices
Xenones Filotera, Imerovigli — you want a quieter evening and the lowest rate of these three
A few nights on the rim is enough. You do not need a week to get October in Santorini.
Click the hotel that fits. Each button opens the October dates I already checked, so you can see the live rate without starting from scratch.
Enjoy October in Santorini. The cliffs are the same. The evening is quieter. And there is a terrace waiting when you walk back from the view.
Looking for more Santorini planning?
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