Quantum fluctuations of the electromagnetic vacuum produce measurable physical effects such as Casimir forces and the Lamb shift [1]. Similarly, these fluctuations also impose an observable quantum limit to the lowest temperatures that can be reached with conventional laser cooling techniques [2,3]. As laser cooling experiments continue to bring massive mechanical systems to unprecedented temperatures [4,5], this quantum limit takes on increasingly greater practical importance in the laboratory [6]. Fortunately, vacuum fluctuations are not immutable, and can be "squeezed" through the generation of entangled photon pairs. Here we propose and experimentally demonstrate that squeezed light can be used to sideband cool the motion of a macroscopic mechanical object below the quantum limit. To do so, we first cool a microwave cavity optomechanical system with a coherent state of light to within 15% of this limit. We then cool by more than 2 dB below the quantum limit using a squeezed microwave field generated by a Josephson Parametric Amplifier (JPA). From heterodyne spectroscopy of the mechanical sidebands, we measure a minimum thermal occupancy of 0.19 ± 0.01 phonons. With this novel technique, even low frequency mechanical oscillators can in principle be cooled arbitrarily close to the motional ground state, enabling the exploration of quantum physics in larger, more massive systems.Rapid progress in the control and measurement of massive mechanical oscillators has enabled tests of fundamental physics, as well as applications in sensing and quantum information processing [7]. The noise performance of these experiments, however, is often limited by thermal motion of the mechanical mode. Although the most sophisticated refrigeration technologies can be sufficient for cooling high frequency mechanical structures to the ground state [8,9], observing quantum behavior in lower frequency mechanical systems requires other cooling methods. Recent efforts using active quantum feedback have been remarkably successful in preparing motional states with low entropies [10]. Thus far, however, only laser cooling techniques similar to those that revolutionized the coherent control of atomic systems [11,12] have yielded thermal occupancies below one quantum [4][5][6]. Nevertheless, vacuum fluctuations impose a lowest possible temperature that can be achieved using these techniques [2,3]. This limit is now being encountered in state of the art experiments involving macroscopic oscillators [6].The concept of sideband cooling relies on the removal of mechanical energy by scattering incident drive photons to higher frequencies. In general, however, this photon up-conversion (anti-Stokes) process competes with a downconversion (Stokes) process that adds energy to the mechanical system. In cavity optomechanics [7], a light-matter interaction arises due to a parametric modulation of an optical cavity's resonance frequency with a mechanical oscillator's position. When the cavity is driven at detuning ∆ below its resonance frequency, the dif...