I've never stayed at Westender, but have been at the property. It's pretty far into the deep West End, but within a 30 minute walk you can get to the area of Out of Town Pastry and Just Natural. On the way, you will pass a couple bars (The Sunset Pub and another small spot whose name escapes me, right now). Going the other direction it gets pretty rural, so you won't find too much until you get to Orange Hill, etc.