We drive from NJ and drive about 11 hours the first day(Saturday) and stay in Florence, SC. The following day we have a 3 hour ride to the resort.
Not sure where you are in MA, but I guess you'd like somewhere a little farther north than that..on the way home last year we stayed at a Fairfield Inn(brand new) in Wilson, NC. I'm pretty sure that's about 5 hours from Hilton Head.
This year on the way home we stayed at a Holiday Inn Express in Emporia, VA, about 6 hours away from the HH resort-it was $79/night as was the Fairfield Inn.(
AAA rate). Very nice, comfy hotel. Probably be about a 12 hour drive from the Boston area.
I like to do the bulk of our driving the first day on the way down, so we're at the resort by noon the latest on arrival day-and on the way back I like to stay at the resort for a good portion of the day before hitting the road, that's why we don't split it up evenly between our 2 travel days.
ETA-just saw that you do have your location listed.
Emporia, VA is about 11 hours form you, so I'd stay there. Get through all the cities on Day 1 and then you just have the easy ride on 95 through the Carolinas on Day 2.
If you feel like pushing, Wilson is 12 hours. Lumberton is 13.5(stayed at the Fairfield Inn there-it was good) and Florence is 14. We stayed at the Country Inn and Suites in Florence and it was nice. we've also stayed at the Wingate there and would again.