Of course! It all depends on how many "slots" your Member of Congress can fill in the Academy. They are allowed a maximum of 5 distributed throughout the 4 years. So, lets say your Congressman representing your district has 1 senior, 1 junior, 1 sophomore, and 1 freshman, after graduation that will leave 2 slots open for him to fill, so 2 appointments from the same district can be made.
Also, there can be Senatorial nominations, VP nominations, Presidential nominations, ROTC noms, etc etc etc, so people from the same district can get appointed, but off of different slates.