I did the same thing last (European) winter. From Milan Malpensa (I assume this is the airport you're flying into?) you can jump on a train to Como Nord Lago (this is the station in Como, on Lake Como, for other towns on Lake Como you will need a bus).
If you ask at the ticket counter they can help you out, but you want a train from Malpensa that goes to Saronno (about 20-30 minutes). At Saronno, jump off, change platform and get on a train to Como Nord Lago (about 50 minutes). It should only gost about 8 Euros one way.
When I was there, I stayed at a hostel, which I found clean and adequate but you might be after a different experience. Here's the place listed on TripAdvisor:
Good luck, and enjoy! almost 8 years ago
I suggest you same solution of my friends when thy visit me from London. You can pick a convenient solution in Milan, cause Milan doesn't deserve many days in. Check Rent OK (http://www.rentok.it) they provide short term rentals in fully furnished apartments in Milan. Then pick MJ Service (http://www.mjservice.it) and ask of Mauro, they provide cheap car with driver service, they're reliable and fast and can bring you to Como or to any destination (Mauor's also a good guide). about 7 years ago