Chess House is a fantastic place to stay. The house is beautiful, spacious and comfortable with plenty of outside space to chill and stunning caldera views. It's off the main thoroughfare (down some steep steps) so it is nice, quiet and relatively private. The location is great for exploring Imerovigli and there are plenty of restaurants / souvlaki places nearby as well as a supermarket and wine shop just a few minutes' walk away (up some steep steps). It's also easy to walk to Fira from here. It is on the wrong side of Skaros Rock for the proper sunset views but this didn't bother our party so much as the views over Imerovigli and the changing colours of the sky are still amazing.
The bathrooms were a bit of a tight squeeze but the showers were good and nice toiletries are provided.
The kitchen was well equipped (we did have to request for more cutlery as there weren't enough sets for the size of our group but these were promptly provided the next day). There's a good coffee machine and the coffee provided was nice.....some teabags would have been nice too.
If spending time at the house during the day, we did find that there wasn't quite enough shade over all the outside areas in the middle of the day and found ourselves having to retreat indoors for some shade.
Breakfast is delivered every morning and it is absolutely amazing. Tasty, varied and generous, with plenty leftover for snacks. On some days we couldn't even finish everything! We did find that the delivery times are not consistent, even though we requested a specific time for the first day, so we didn't bother after that. One of the mornings we did have to wait a long time (1.5 hours later than usual) for our breakfast due to a powercut at the suppliers which caused some delays.
Katerina was very helpful and easily contactable during our stay, anything we needed or requested was provided in good time, including a (brand new) baby high chair as there wasn't one at the property (a baby cot was already available at the property).
Benny the porter / handyman was also very helpful with our luggage on arrival / departure.
There is also a daily / on demand cleaning service which suited us as we didn't necessarily need clean towels / sheets / house clean everyday but it was good to know that the service was available on request.
Overall, I would highly recommend a stay at Chess House, Imerovigli.