I would like to smuggle my 14 inch laptop into boarding school, what is the easiest way to do it?
Is it checked somehow (e.g. Entry controls, pocket check, etc?)
No
Taking into account the demand (see above), it should be very easy. Pack the laptop in the bag with the clothes and then do not use it conspicuously in the boarding school or leave it somewhere where everyone can see it (→ stow it back in the bag after use).
Why are you not allowed to take your notebook with you to boarding school? I know it so that you can take the electronic devices with you, but the usage times are reduced in the lower classes - which makes sense. So: go to your educator and ask him if you can take your notebook with you and offer him a regulation on the restriction. And if he refuses you, leave the device at home. It's confiscated at boarding school faster than you can see, and then probably only your parents can pick it up!