Wintertime in Crete is warm. The island is located closer to Africa than any other island in the Aegean Sea, so despite the fact that I visited it in early December the temperature was around 15-20 degrees Celsius, a comfortable one! An extra bonus as this way I managed to avoid the summertime heat!
There were plenty of hotels ready to welcome me. Not as many in operation as you will find in summertime but in any city, if you spend a bit of time to look around you will find plenty of choices at good prices, even better in wintertime!