On one of my charter trips to Boston, I had a little time to explore and found a really nice little airport about 25 miles SSE of downtown Boston called
Norwood. What a cool little country-style airport. They had a couple of flight schools and an airport cafe. If you don't want to deal with the Massport hassles, you might check this place out. The two flight school/rental outfits have links on the airport website. Prices seem to be in line with nationwide averages for the types and age the aircraft. Whatever you decide to do, enjoy Boston.
Best,
Westhawk