One vote for Newburgh.
We liked the Homewood Suites at the Stewart Airport for A-Day. A 'suite' room there is no more costly than regular rooms elsewhere (sometimes cheaper!).
A-Day we met up with our Cadet, ate lunch in Highland Falls and then headed back to the Homewood Suites. About a 30 minute drive. A little closer than Fishkill. All they want to do at this point is sleep. He went in the bedroom and closed the door and we hung out in the living area. It also has a small kitchen. So I made him his favorite dessert and packed it up for his boodle box. When he woke up we ordered delivery pizza. We ate and talked and he was back at West Point by midnight.
Word of advise: Don't show up at the gates at 10 minutes til 1:00am. There will be a long line of cars trying to get their cadets back for 1am Taps. We left plenty early to make sure that there was no problem with traffic.
Next morning we noticed several cadets at Breakfast. Their parents had gone and picked them up and brought them back to the hotel for breakfast (which is included at this hotel). We met DS for church, then brunch at The Thayer (they give cadets 1/2 off for the brunch!). He took us to the PX and let us buy him school supplies.
On occasions where they let the cadets have extended walking privleges, I think it is not worth paying $$$ for Highland Falls hotels. You have time to make the drive to the surrounding towns for nice hotels that haven't jacked up the prices. JMHO.