Central Sorrento is mainly flat and, in my opinion, this is the best place to stay but there are some villages in the hills. Positano is a beautiful village, almost vertical with a lot of steps and smaller than Sorrento.
My photo album is below and shows a lot of good hotels but I wouldn't say any of them were "quirky" but certainly clean. Move your cursor onto each pic to see where it was taken in bottom left.
EddieEdited: 18 March 2018, 20:03
Visited beautiful Taormina last April and Sorrento many times. The town itself is flat. There are many hotels on the flat such as Antiche Mura, Palazzo Guardati, de la Ville, Royal and Ambasciatore with rooms to suit many price ranges. There is a lift in Villa Communale Gardens to Marina Piccola from where you can take boat and ferry trips. You can walk down to Marina Grande that's an authentic fishing village. There are hotels in elevated positions such as Capodimonte, Bristol, Belair, Minerva and Minervetta where views are wonderful. Minervetta (on high) and Guardati (centre) could be called quirky! We book for superb views. Have visited every hotel mentioned and stayed at Ambasciatore,Bristol,Capodimonte and Guardati.
Up in the hills? The higher the hotel the more chance there'll be of a shuttle bus service.
Hotels I've mentioned in elevated positions are an 8/10 minute walk from centre of town. People of all ages enjoy staying in these hotels.
I'd stay in town on the flat if I were you.
For hotel advice, please post your nightly budget.
Personally I would stay in town as in the evenings it's fun to just get out and stroll around and find a nice little bar tucked away, or sit in the main square people watching. Yes the Hotels in the hills have shuttles but they tend to stop in the evenings as they want to keep you in the Hotel. Also, if you want to get out and about you have to get down from the hills before starting your journey. Sorrento town has a bus station and also the port to catch ferries to Capri and the aliscafo over to Naples. Also the train station is in the centre of town and you can get to Pompei, Herculaneum and Naples easily on the train. There are many nice Hotels both large and small to choose from. Enjoy, it's a fascinating place!