A month ago the answer on the eating/drinking front might have been Hotel Herman, but they lost their lease and had a speedy demise. *SNIFF*
In the same neighborhood (Mile End/northern stretches of St Laurent) is
Lawrence, doing a Montreal take on London neo-bistros (my,
how far we've come). Small-ish list but you'll do fine.
A little to the south,
Le Comptoir and
Lilli.Co are fun, have good lists and good eats, and offer window views onto the Main to watch the world go by.
I've always had a soft spot for
Pullman on Ave du Parc. It gets packed with McGill students on the weekends but it's a little more central than Vin Papillon if all you're looking for is a tipple to begin or end the night.
A couple of other places worth a look, both in the Petit Bourgogne neighborhood southwest of downtown (near Joe Beef):
Nora Gray, for Italian in a really nice intimate space; and
Candide, for set menu. I haven't been to Candide but I hear great things about their list.
Walkability is high but avoid staying right downtown - there's not much there and you'll be shlepping everywhere. If you're AirBnB-ing, set your sights on Avenue de L'Esplanade, Square St-Louis, or the west side of Parc Lafontaine for maximum immersive effect. All of those are short walks from *the action.* Pre-sharing economy,
Castel Durocher was a lovely option.