Large scale infrastructure expansions in hotels are exposed to uncertainty. Since the costs involved in these expansion projects are high and often irreversible, hotels would benefit from analyses that incorporate uncertainty along with traditional valuation techniques like the discounted cash flow (DCF) method. Decision tree analysis (DTA) and real options analysis (ROA) have been in use for the past couple of decades to handle uncertainties and optimize investment decisions. DTA provides a distinct approach to strategic investments that quantitatively takes into account the uncertainties involved in the investments. Under uncertainty, the decision about whether to expand is analogous to the decision about whether to exercise an American call option. By using ROA to the hotel expansion scenario, managers can in-corporate and quantify, flexibility and timing in their analysis. The objective of this chapter is to detail the DCF, DTA and ROA methodologies and their applications specific to hotel expansion investments.