Cortona

You might have better luck with responses if you post this in the Italy forum. This forum is for reviews of restaurants and hotels, generally limited to kudos for a good place or critiques of someplace unpleasant. Posting your query here will limit the number of folks who see it.

We spent a week in a hotel below Cortona, down the hill. We had already spent time in the Chianti region and Florence. Mostly, from Cortona we drove into Umbria and Lake Trasimeno. We liked Umbria so much that we returned there for a two week stay in Spello a few years later. We went to Montalcino and Pienza in Tuscany from Cortona .We liked Cortona and I don’t understand why it gets a bad rap.

I agree with the others about using the Italy forum: https://community.ricksteves.com/travel-forum/italy?direction=desc

However:

We’ve been to Tuscany many times and Cortona is one of our favorites. As an alternative, take a look at Montepulciano, which has become our favorite place to stay.

If you decide you are interested in Montepulciano, I can suggest 2 places to stay. The first is in town and is an apartment rental – http://www.charminghomesmontepulciano.com. Nice apartments and nice host. The second is a bed and breakfast – https://www.fontemartino.com. It’s just outside of town, which may be what you are looking for based on your post above. The owners are wonderful and it is walking distance to town. It took us about 30 minutes to walk there when we stayed this past summer.