Northern Italy is one of my favorite places. We spent a good period of time there after visiting Rome/Florence/Venice. (Take the train out of Venice to Verona and rent a car. We have good luck with Auto Europe.) Driving north along Lake Garda toward Bolsano as an entry point to the Dolomites.
The Olympics will be held in Cortina and in Milan. I am not sure of the winter weather in the Dolomites because we have only been there in the Summer and Fall. I would guess with all of the visitors roads will be cleared. You could also stay in Bolsano or Trento and take a bus. There are many smaller cities with excellent places to stay. We like La Villa. It will be tough to get a reservation in Cortina. It you don't want to deal with snow, Milan is the best bet. But, please keep the Dolomites on your bucket list.
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