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Heat a large cast iron skillet over medium high heat. Add bacon and cook until brown and crispy, about 6-8 minutes. Drain excess fat; transfer bacon to a paper towel-lined plate.
In a large bowl, combine broccoli, cheese, cashews, onion, cranberries and bacon. Stir in dressing and gently toss to combine.
Cover and chill at least 1 hour before serving.
In a small bowl, whisk together mayonnaise, milk, sugar and apple cider vinegar.