Santorini area in october
 

Which is best Fira or Oia for beginning of October?

Best in what way?
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We stayed in Santorini for 3 nights, arrived on 10/10/14. We stayed at Aressana Spa Hotel & Suites which was in Fira. It was very nice hotel with great breakfasts.

Things are winding down at that time of year; places are starting to close. It wasn't crowded [a bit when cruise ships were in port]. The weather was lovely.

Which area for a hotel will be best to stay, were restaurants open then?

We were able to find places to eat, not to worry. We were pleased staying in Fira. Can't say that Oia is better or not.

Does the aressana spa hotel have caldera views?

They are set across the street so you can't see the calera from rooms. However, if you walk out the front door, and walk 50? 100 ? feet, there is the perfect view for sunset. Do a google map search for the hotel, look at it in 3D

Santorini has a longer season than most other Cyclades islands, and I wouldn't hesitate to stay there in October. I've stayed in Oia a couple of times in May, which is also outside the main season, and it was very pleasant then. I remember how peaceful it was in the mornings before the day trippers began to arrive.

Fira is larger and more central. There are also other caldera villages near Fira, so you can choose from more than just those two.