For our vacation this year we drove from Chicago to the South Haven, MI area with our two boxer lab mixes Socks and Boots. We rented a dog friendly home in Bangor on a horse farm. We had booked this place for a weekend last year and wanted to stay for a week over the summer. We live in a townhouse so our dogs loved the grass and space to run around.
Our dogs even made a friend with one of the dogs on the farm.
All the Lake Michigan towns have cute little downtowns with outside seating areas. We took the dogs for a stroll down South Haven's downtown area and to the lighthouse. We got food from one place in downtown South Haven but we placed an order to go and took it back to our rent house. My husband is vegan so we had to also look for vegan friendly places while on vacation.
There is a small dog beach in South Haven but when we went there this year, the beach was washed away. We also went to another beach nearby and the same thing (Saugatuck I think). We did however, find a dog beach in West Olive, a little past Holland. Kirk Beach is $7 for non-residents and is about 1/2 mile hike from the parking lot. We took our dogs there a couple of times and they absolutely loved it.
One of the other places we went to was Dutch Village in Holland. We only walked around the shops but dogs area allowed to be outside the shops and it mentioned online that they were allowed in the amusement area. Holland claims to be very dog friendly.
Not all beaches are dog friendly so check the area before you go but most outdoor things are dog friendly and there are a lot of dogs in the area especially the downtown areas. We also took our dogs to the Kal-Haven Trail. It is a 30 mile trail that goes from South Haven to Kalamazoo. By the end of the trip our dogs were pooped out!