The Manchester airport is tiny and easy to navigate. I used to fly into it all the time before Southwest went to Logan. If that's where you're going in the end, I'd fly direct unless it's prohibitively expensive or at 5am. If that's the case, Logan is also totally fine and has one of the prettier approaches of any airport--you loop in over the ocean and fly low over the harbor islands before landing. Get your luggage, catch the free Silver Line bus to South Station, and go from there.

Hotelwise, the lazy way would be to stay at an airport hotel and then take the T into Boston or Cambridge for sights/eats. You could stay anywhere off the Red Line too, but it's more $$$. If you're VERY lazy, stick around the airport, Eastie has a ton of good Salvadorean food.