Optimal stopping is a fundamental problem in optimization that has found applications in risk management, finance, economics, and recently in the fields of computer science. We extend the standard framework to a multi-agent setting, named multi-agent optimal stopping (MAOS), where a group of agents cooperatively solves finite-space, discrete-time optimal stopping problems. Solving the finite-agent case is computationally prohibitive when the number of agents is very large, so this work studies the mean field optimal stopping (MFOS) problem, obtained as the number of agents approaches infinity. We prove that MFOS provides a good approximate solution to MAOS. We also prove a dynamic programming principle (DPP), based on the theory of mean field control. We then propose two deep learning methods: one simulates full trajectories to learn optimal decisions, whereas the other leverages DPP with backward induction; both methods train neural networks for the optimal stopping decisions. We demonstrate the effectiveness of these approaches through numerical experiments on 6 different problems in spatial dimension up to 300. To the best of our knowledge, this is the first work to study MFOS in finite space and discrete time, and to propose efficient and scalable computational methods for this type of problem.