Ashland hotels and motels with swimming pools that are perfect for a family are listed below. Search for cheap and discount hotel rates at hotels with a pool in or near Ashland, WI for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Ashland Wisconsin hotel and motel rooms for children. Review the list of Ashland hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids. Planning group travel? Get Ashland WI Group Hotel Rates