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Tuscany recommendations - where to stay

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Does anyone have any recommendations on where to stay in Tuscany? Specifically somewhere in/near Siena or in the Val d'Orcia region (Montepulciano, Pienza, etc.)?

Do you recommend an agriturismo, B&B, apartment, or hotel?

It is for two people and we will have a car. I'm not sure whether we should stay in a town or near one. Originally I had thought that it would be a fun experience to stay in an agriturismo and have dinner there a few of the nights, however, maybe it would be better to be in a town so that there is more to do at night and maybe then we wouldn't have to drive as far.

Suggestions?

Thanks!

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