Blue Harbor is about 25 minutes north of the Blue Barn in Sheboygan. It has a water park and is near South Pier which has super cute places to mini golf, eat ice cream, etc. We would recommend staying here if you are staying with a larger group and are making a weekend vacation out of your stay!
The American Club is another great option if you plan to make the weekend into a vacation. Although it is a little pricier, Kohler has many wonderful lodging spots (the American Club and others) for a nice get-a-way. Kohler is 20 minutes north of the Blue Barn.
Port Washington is about 20-25 minutes south of the Blue Barn. The Inn & Suites would work wonderfully for anyone in town for 1 night and flying out of Milwaukee or Chicago airport!
Milwaukee is about 45 minutes south of Oostburg. Milwaukee is a great city to hang out in for the weekend or you could find a hotel near the airport if you are flying in. If you are wondering about the neighborhood that a hotel is in, feel free to text me (Allison) as I drove throughout the city for my social work job and know the neighborhoods well :)