"The prettiest village in Maine", Wiscasset is a thriving tourist destination noted for early architecture, majestic settings, and a rich history as the shipbuilding, fishing, and lumber seaport center that nearly became the state's capital. The town's population of just 3,732 resides on roughly 28 square miles overlooking the Sheepscot River. Your search for vacation rentals in Wiscasset, Maine will lead you to an area so rich in small town charm and intriguing history that you'll find yourself yearning to return year after year. Famous architectural landmarks like the Nickels-Sortwell House and Castle Tucker retain a window to the past as stellar examples of 19th-century Federal-style mansions. Visit one of the oldest remaining jails in New England - the 1811 Old Lincoln County Jail (with attached Jailer's House), and the Lincoln County Courthouse (the oldest functioning courthouse in New England) for a glimpse into the history of our criminal justice system. Families will bask in the thrill of Monkey C Monkey Do - Maine’s premier zipline and adventure park. With over 60 obstacles, eight zip lines, kid-friendly courses, laser tag, and a giant swing, there's a challenge to delight every age and skill level. Those seeking more natural recreation will appreciate the vibrant waterfronts, meandering trails, and white sand beaches. Visiting foodies are sure to make a beeline for Red's Eats, a small takeout restaurant that has received widespread praise and media coverage as the home of "the best lobster roll". Plan your visit early and be prepared to wait as this kind of fame has also led to the eatery being responsible for the biggest traffic jams in Maine.