Lots of folks just camp, so that's an option if you're rough and ready. A step up from that (not a big step) is the Summit apartments.
Getting some guys together to rent a house is IMO the best option, it's not always the cheapest but if you pack a few people in it can work quite well. One landlord to try is "An Oregon Experience" which manages several homes in Government Camp, Welches, Sandy etc. Just make sure to communicate courteously and professionally as the local landlords are usually not loath to rent their homes to a gaggle of untidy ski bums.