End a night out in your own private Jacuzzi at Le Petit Prince (from $150), a four-room boutique bed-and-breakfast housed in a Victorian-era townhouse that doubles as an art gallery. In the morning, savor creative fare like shirred eggs in curry cream next to the dining room fireplace or on your in-room balcony.
Wake up to a view of the Frederick Law Olmsted–designed Mt. Royal Park from your room at Casa Bianca (from $129). The 1912 French Renaissance revival townhouse features five bright, open rooms with light hardwood floors and white-paneled walls, four of which look over the park and the tree-lined esplanade below. For added style, book the enormous two-room Marie-Anne suite for its sliding French doors and turret windows.
Sleep right above an intimate, 55-person indie music venue at Pensione Popolo (from $40), the surprisingly quiet upstairs hotel of Casa del Popolo, which also houses a bar and bistro. The rooms are functional rather than fashionable, but the price and location are unique and the booking includes two free tickets to concerts (past performers have included Xiu Xiu and TV on the Radio).