Between July 1 and September 15, it can be very difficult to find accommodations. Try calling ahead from Athens to book a room or book before you leave home. Note that many of the "luxury" hotels were thrown up quickly some years ago, and some have since been managed and maintained poorly -- so if you plan an extended stay at a beach resort, we recommend you first check into one of the hotels in town and then look over the possibilities before you commit to an extended rental.
If you crave the restaurant/shopping/nightlife scene, or you've arrived without reservations at one of the resort communities, try setting up base in Skiathos Town. From here, you can take public buses to the beaches on the south coast or go on caique excursions to the spectacular north coast or other islands.
Families often prefer to stay in two- to four-bedroom villas outside of town or at hotels overlooking a beach, with only an occasional foray into town.
One of the most pleasant parts of Skiathos town is the quiet neighborhood on the hill above the bay at the western end of the port. Numerous private rooms to let can be found on and above the winding stairs/street. Take a walk and look for the signs, or ask a travel agent. All over the hillside above the eastern harbor are several "hotels," basically rooms to rent. You'll be surprised at which buildings turn out to be lodgings.
By the way, the in-town hotels (Alkyon excepted) cannot provide adjacent parking, but there are possibilities at the harbor's far eastern edge.
In & Around Skiathos Town -- Consider Hotel Athos, on the "ring road" that skirts Skiathos town (tel./fax 24270/22-4777), which offers ready access to town without the bustle; and Hotel Meltemi, on the paralia (tel. 24270/22-493), a comfortable, modern place on the east side of the harbor (the front units can be noisy).
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.