Not All Prisoners Are Eligible. Residents typically stay one to six months, but some stay for as long as a year. During this time, prisoners must pay the halfway house a fee, usually equal to 25 percent of the prisoner’s gross income.Prisoners must also pay for their own medical care (other than drug treatment) and health insurance.he federal government and the states have spent billions of dollars on halfway houses, assuming that they would cost less and cut down on recidivism. In general, placing a prisoner in a halfway house costs the government about two-thirds what it costs to keep that person in prison or in jail.