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Montepulciano accomodations and Montone

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For our May trip, we thought we would fly into Rome, take train to Florence
Florence 3 nights, get car, San G 2 nights, Siena 2 nights and then Montepulciano 2 nights. (Yes, I know it's lots of moving but we like to see a place in the evening, have dinner there and not have to drive at night in unfamiliar places--we don't mind driving during the day)
What would be a nice place to stay in Montepulciano--something around $150 per night (could go up a little).?
We would like to see some of Umbria and it was suggested that we should stay in Montone as we could get to Perugia, Spoleto, Assisi, etc. from there. What would be a good place to stay there? Also, would we be able to get from there to Rome for our flight back (12 PM flight) or should we get closer to Rome the night before?

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