Chestnut Mountain Resort
Set amid the rolling hills about 8 miles outside of downtown Galena, Chestnut Mountain makes a top choice for families with its year-round recreational activities and indoor pool. While your east- and west-coast friends may ridicule Midwest skiing, you can thumb your noses as you woosh down the resort's 19 downhill and snowboarding runs. During summer months, guests take advantage of cruises along the adjacent Mississippi River—be sure to request a room with a river view—along with the property's own mini golf and disc golf courses, and 5 miles of trails for hiking and biking. No need to bring your own two-wheeler, just rent one for the day from the hotel.