The best area to stay in Oakland, Maine, is near Messalonskee Lake, particularly the areas around the Belgrade Lakes region.This area is characterized by its natural beauty, focusing on lake activities and a relaxed pace. It offers a mix of accommodations, from lakeside cottages to more traditional lodging, with easy access to the lake for boating, fishing, and swimming. The main street in Oakland village, Water Street, features local shops and eateries.For families, staying near Messalonskee Lake is an excellent choice. The lake provides numerous opportunities for outdoor recreation, keeping everyone entertained. Many properties offer direct lake access, allowing for spontaneous swims or boat trips right from your doorstep.Couples looking for a peaceful getaway will also appreciate the tranquility of the lake region. It's an ideal setting for enjoying scenic views, quiet walks, and dining at local establishments that often feature fresh, regional cuisine.