I meant to add directions for the 10 minute walk from Terminal E arrivals to the BOS Hilton.

The TL;DR is to follow the signs to Terminal A, then after a couple of minutes you should start seeing signs to the Hilton. If the Hilton signs appear to evaporate, refer to Terminal A signs for backup. Around half way, you should be able to see the Hilton building to your right as you walk along.

More detail…

There are a series of escalators, lifts and travelators to take, but as long as you keep eagle-eyed on the signs, you should be OK. The entire route is covered and almost entirely enclosed throughout its length: I didn’t need to put on my coat despite the outside temperature being -11C.

When you arrive at the Hilton, you’re initially on the meeting room/conference level (hotel’s level 2). After passing through this section, you’ll find yourself overlooking the lobby atrium, and can then either take one of the hotel room lifts or the escalator down to the lobby level to check in.

When going back to Terminal E, for a quick exit, you can avoid the lobby level entirely, and take the lift to the hotel’s level 2 instead, back through the meeting room/conference area, and back the way you came, following the appropriate signs to Terminal E.