AcademyDad--My son is in his second year at West Point and has thived there both academically and on the baseball field. We have found it's easiest(less traffic hassels and easier to navigate) to fly into Newark Airport. The drive is is about 45 min to 1 hr 15 min depending on the time of day. The motels in Highland Falls were built in the 50's and 60's. There is a new Holiday Inn Express there now. Newburgh does have many of the newer chain hotels. Good luck to both of your sons.