Legal Question in Business Law in Massachusetts

Your question involves a very complex answer. If you want to run a sweepstakes online, you have to find a jurisdiction where it is legal to do so. You would have to host the website in a jurisdiction where your sweepstakes is legal. You would need to form an offshore corporation as well.

Notwithstanding all of that you would need to make sure that the type of sweepstakes you are running is not illegal for US citizens to participate in, if it is you cannot allow US Citizens to participate, otherwise notwithstanding you would not be violating foreign laws you would still be subject to US law including criminal charges if applicable.