We've been to HH several times, but have only stayed at the Hilton resort in the Palmetto Dunes development. All rooms at the Hilton have kitchenettes, and it is oceanfront. It also has its own bicycle rental on-site, and is on the bike trail system (one of our favorite features of the island). The hilton also has its own nice places to eat/drink, a spa and beautiful, lush grounds.
The drive is long and boring, but worth it. We usually just stay on interstates the whole way (until you have to turn off I-95 to get down to the island).
The island itself is a wonderful, slow-paced, relaxing place to "get away from it all". They have very strict signage, design and landscaping ordinances, which we love. There are plenty of good restaurants, from traditional seafood to many ethnic types. We also like to bicycle to Shelter Cover marina when we're there. You can stroll what seems like miles of docks and admire all the boats, water and the wetland landscape.
Cute shops can be found at Coligny Plaza, an open-air shopping center on the main, "public" part of the island, and of course at Harbourtown, at the South end of the island in the Sea Pines development. Don't miss The Salty Dog cafe and shops in the South Beach area, also in Sea Pines. There is also a regular mall on the island and outlet shopping in Bluffton, which you pass thru on the mainland just before going over the bridge to the island.
Hope this helps - these are just some of the things we've done on our few trips to the island.