You could use events something like this (you would change the image rather than the colour);

Code:
Private Sub SetPictureBox()
        If (CheckBox1.Checked) Then
            PictureBox1.BackColor = Color.Red
        Else
            PictureBox1.BackColor = Color.Blue
        End If
End Sub

Private Sub CheckBox1_CheckedChanged(sender As System.Object, e As System.EventArgs) Handles CheckBox1.CheckedChanged
        SetPictureBox()
End Sub

Private Sub CheckBox1_MouseEnter(sender As System.Object, e As System.EventArgs) Handles CheckBox1.MouseEnter
        PictureBox1.BackColor = Color.Green
End Sub

Private Sub CheckBox1_MouseLeave(sender As System.Object, e As System.EventArgs) Handles CheckBox1.MouseLeave
        SetPictureBox()
End Sub