Yes. You can send text messages to up to 50 recipients at one time. In the text window, simply click the Add People button and start sending your text messages. You can add contacts (hold down the Ctrl key on your keyboard to select multiple contacts) or enter a phone number in the box provided. When you’ve added your contacts, click Select, then click Add to add those contacts as recipients.
Be aware that you will still have to pay for each text message that you send. For example, to send a text to five recipients you will be charged for five text messages.
Not sure how to send texts from Skype? Check out this handy guide.