If you're looking to discover somewhere new, look no further than Windward Side. Whether you're planning to stay for a night or for the week, the area around Windward Side has accommodations to fit every need. Search for hotels in Windward Side with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Windward Side hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Windward Side hotel deals are here with our lowest price guarantee.