Aside from weddings, people who do not work in an entertainment business rarely think about booking live musicians. But arranging to have a small house or gallery concert can be easier and more affordable than you may think, as well as more enjoyable.
All you need for space is a living room or dining room whose furniture can be arranged to have room for 1-3 people and their instruments at one end/side, and for your audience to sit in folding chairs/ on pillows, etc. Alternatively, you may find an art gallery, store, or other space that will rent its use to you for a reasonable fee – for instance, Outpost 186 in Cambridge is available for $75 an evening.
Next choose your performer(s). A solo acoustic singer/songwriter/performance artist will be easiest to fit into a residential space, but I’ve performed with 4-5 piece bands at house parties. The questions to ask a band who will perform in your residence include: