Buongiorno,
If you only are dedicating three days to this area I am not sure you will make it to Cortona because it is a little bit further east and isolated from the other destinations.
You could still stay in Val d'Orcia without being to far south, have a look at http://www.tuscanyaccommodation.com/...in-poggio.html
or go over towards http://www.tuscanyaccommodation.com/...vo-berardenga/
I especially like: Borgo Argennina and Agriturismo Incrociata.
Buon Viaggio,
Donna Denise
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