Cortona

I stayed at Le Gelosie in 2007 and was pleased with my stay there. I was on the top floor so some 70+ steps up. This is a small place with 4 rooms, one per floor. It is just off Piazza Signorelli. When I was there, they gave me a "ticket" for breakfast that I could use at a local cafe for a croissant and coffee. You might want to check the reviews on tripadvisor to see if there is info from someone who has stayed there more recently.

I stayed at Casa Kita last May. Price was 60 euro for a room with large double bed and bath. Room was very nice and location is close to Piazza Garibaldi. Also had a nice shared terrace overlooking the valley.