There are some really nice hotels on the Boston waterfront and there is a water taxi from Logan airport to those hotels, so no need to rent a car. The North End is chock full of great food places and easily walkable from the harborfront hotels. All of the downtown area is walkable from there as well. No shortage of good places to eat.
And we stayed here several years ago on our way back from Nashville. It's a cool place, but again, it was years ago. I'm not sure what they have for dining and entertainment now, but it might be worth a look.
https://www.frenchlick.com/hotels/westbaden