Originally Posted by YYC_BOS_and_Back
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Don't know too much about the hotels in either place, but the airport is across the harbour from downtown - about a 5 minute ride on the subway. Getting to/from the airport itself on the subway is a bit of a hassle with inter-terminal transfer buses to the subway station, and then the subway itself. If money isn't a big deal would suggest just grabbing a taxi on arrival / departure, but definitely use the T for going out and about for the day.
No need to bother with taking the shuttle to the Blue Line subway anymore. A better alternative is to take the new Silver Line bus that stops outside each terminal—runs about every 10-15 minutes.
For just $1.25, the Silver Line takes you directly into downtown's South Station where you can also transfer free to the Red Line subway (if you're going to Cambridge or heading to Downtown Crossing, etc.)
Link for MBTA route info
It's a bargain compared to the chance of getting stuck and running up the meter in tunnel traffic along with all the surchages tacked on. If you want to cab it, get one after you exit South Station.
Stay at a hotel in the city since Boston is all about walking. The airport hotels aren't convenient enough to step outside and get to where you're going to see the sites. Plenty of accomodations to choose from too.