We stayed at the Hyatt House in Fishkill last summer when we picked my son up from SLE. Very nice, new and clean and the drive is not too far to WP. There is also a SAMS club and other shopping within very close walking distance. I highly recommend it!
Fishkill works well, especially for things like A-day weekend. (you are thinking ahead to then)
Sams + Walmart + Cracker Barrel + pretty much every chain restaurant you could name. Big win for A-day weekend. Sams hot dogs & pizza were hungry cadet's favorite. Cheap and fast!
Unless you swung a room at the Thayer, we've found the hassles of trying to stay in Highland Falls/Ft Montgomery not to be worth it. Restaurants overloaded and the hotels gouge badly. And Thayer gate has the most delays.
I'd be selective for Newburgh hotels, though any out near the airport will be fine. But it's only about 20 minutes more across the bridge to Fishkill and there are many more hotel and eating options. Plus theaters nearby, etc.
For three day weekends where you are off post once released we have even done Danbury. Central Valley works well, but only has a couple of hotels and they book up fast.
Mahwah is usually our last resort. Hotels are OK, but the drive is more of a hassle and we have found dining service to be very bad in NJ. In fact, we now pretty much bypass NJ whenever possible.
BTW, It's worth picking up a tollpass at a grocery store. Want to say they are about $20 and come loaded with $20 in tolls. You'll use it while the cadets are at USMA over the years and it's good elsewhere. Just makes bridges and interstates much faster. We bring it with us even if renting a car.