The last couple times I flew out of Logan over the past few months I either took the Amtrak to Boston from Kingston (which has a free lot, I parked here for 2 weeks with no issues) or I parked at Braintree. It's $7 a day and the shuttle was $18 round trip If you did want to do a hotel in Boston, I got a really good rate staying at the Bostonian in the North End when I got back late from a flight from Italy last month. Otherwise you're looking at like $100 or more for an Uber or one of the other private services. You can schedule ahead of time.