The epic island of Santorini (Thera) is merely 30 square miles and only 40 minutes end to end, but there is a great diversity in places to stay. You can spend a ton, or just a little and probably not go wrong with any choice you make. The differences will be based entirely on your location and amenities--whether you need a pool or a view, whether you want to be near beaches or shopping or restaurants.
The Holy Grail of the island is the previously quaint, still picturesque village of Oia at the north end of the island. Quaint because streets have no names. Picturesque, because one main 'path' meanders past shops and restaurants from one end to the other of a town that overlooks the magical caldera and delivers an out-of-this-world sunset.
The very best hotels are situated with caldera views. These hotels are also the most expensive and can be over $1000/night in high season. These will generally be cliffside. Keep in mind, most beaches are situated on the opposite side of Santorini.
There are many affordable and less expensive options, but these will not have caldera and sunset views as they will be located more inland. What they ARE more likely to have is parking! If you want to have a car while on the island BE SURE you rent a place that provides a place to park your car, otherwise you're going to be VERY unhappy!
Also keep in mind that since the caldera-view accommodations are essentially built into a cliffside, most places will look somewhat similar to one another. They will be cave-like inside and probably have a small patio with a view.
Things to remember to look for when browsing places to stay:
Do you want a water feature?
Do you need a pool or is a hot tub ok?
Does your pool or hot tub need to be private or are you willing to share?
What is the view?
Can your neighbors see full-on into your patio or little house?
Will people be walking by in front of your patio and your view?
How light is the cave house?
Read Reviews: cave houses are basically underground, which means if not properly ventilated, may smell like mildew and dampness. (I stayed in a Troglodyte cave house in France once that was so deep and so damp that the bedspreads were moist to touch and the mildew gave my husband a headache...so we had to move.)
Is breakfast included?
Is this place a 'hotel' or privately owned and managed? Why does this matter? Hotels come with help and services you might need like porters, transportation, recommendations, restaurant reservations, overall guidance, security, a place to complain when things aren't right and so on.
Most people stay in Oia, Imerovigli, Fira or Firostefani.
Oia wins for romance and walkability. Imerovigli wins for solitude and peace. Fira wins for busiest. Fira's has the reputation for the best shopping, and I did do a fair amount of shopping and buying there, I had to wade through a lot more souvenir/junk. Fira is the town that is home to a McDonalds.
I personally like to book my accommodations at Booking.com because you usually don't pay until later plus they generally offer a generous cancelation policy. I've always had great experiences.
I did a ton of research before booking, including browsing 100's of Airbnb.com listings and almost booked a couple Airbnb options. In the end, I am SO glad I booked at more of a hotel-type place for the amenities they provide.
Get a Porter!
Whatever you do, wherever you stay, i highly recommend you hire a porter. Best if done in advance through your accommodations. Armeni Luxury Villas booked ours. He met us at the taxi drop off point (the last place you can drive a car in town--which is basically at the post office), grabbed 2 pieces of 40-pound roller bag luggage and 2 10kg pieces of carry on luggage and off he went, leading us through the winding (crowded) streets and stairs of the village of Oia. See what it looked like here and here.
The streets are not named in Oia, so if you have never been there before, good luck finding your hotel! Would you want to do that with all this luggage in tow? Not me.
We simply drafted in behind our porter who was like a donkey. He dropped us in front of our concierge and took our luggage to the room.
Utter Luxury Hotels
I loved the spa here. It's a cozy, cave-like, quiet, luxury environment. Like all fancy hotels, they treat you like royalty, and paper panties will be on hand for your massage pleasure. (I live in the US where paper panties are not a thing, so whenever I am abroad and enjoying a spa treatment, these little packets of panties are one of the things that tickles me pink. I bring them home and put them in people's Christmas stockings.)
TBH all the Canaves properties on the island confuse me. I stopped at 2 different ones in town trying to find the one with the spa. Epitome is the newest in their empire, and its location is at the best sunset viewing spot, the unique traditional architecture is a stand-out.
Shows up on a lot of people's 'Best Hotel in Santorini' List. Private terraces, but not all accommodations have their own pool or hot tub.
And...this is why we care about the caldera views. If you're in town to relax, this will do it.
Does it look like 41 suites? Woven together by winding pathways, Mystique makes a little village all its own.
It's a very nice view...but as you can see there is a row of villas between you and your view of the sea.
Stunning, right? Quiet. Lovely.
Some of My Other Favorite Santorini Hotels
Cave hotel perfection with a breathtaking caldera view. A few steps down the hill from the main path of Oia, smack in the middle of town, this set of 3 unique villas is quiet and private (Celebrities often rent all 3 at once, so that will tell you how wonderfully private they are). You won't have people walking past you en route to somewhere else. Each has a patio and private hot tub or pool where your custom breakfast order is served each morning at the time you specify. The concierge (Veronica) is better than working with someone from a 5-star city hotel. She will arrange everything, tailor recommendations to your whims, and generally watch over your every need. You will feel loved and pampered. (Do NOT get this place confused with Armeni Village Rooms & Suites...they are a different hotel altogether on the south end of town--less privacy)
Click here for my video tour of our room here.
Located beneath the windmills, this beautiful collection of villas has THE view everyone is looking for when they come to Santorini. We stumbled upon it just before sunset and went in for a really good dinner. The patio was quiet and the setting sun was unobstructed. After being on the island for 4 days, this was the first time I was able to 'feel' the sunset. Our patio dining seat looked back upon everyone else off in the distance, sitting on the walls of the Oia Castle waiting for the orb to drop below the sea. We could hear them clapping when the sun dipped below the horizon.
These are sweet...the only downside is they are located at the beginning of Oia village and therefore a 15 minute walk to the center of town. If you don't mind not being in quick access to things....
Beautiful, spacious villas. Pay attention that all of them have access to a communal infinity pool and only some have private plunge pools. Technically, located in Imerovigli, it is actually situated on the ancient path between Oia and Fira that passes through Imerovigli. Aenaon (hard to write!) is actually between Oia and Imerovigli. Lots of quiet and privacy, if not a little desolate.
Now that you've picked your place to stay, check out this for the utterly best places to eat in Oia
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