It was our first trip to Astypalea, an island we'd been looking forward to visit one day for years! We loved it, and our choice to stay in this house in the chora made it perfect. It is in a quiet location, on a main path to the church and the Kastro, but even in August not too many tourists went by. (We felt especially privileged to be staying here while they probably were staying at some hotel without personality, but closer to the beaches).
A few bars and restaurants are close by anyway, a 5 min. walk or so. Most of the Chora tavernas are good, I wouldn't really recommend one over the other, trust your own guidebooks. As for bars, there are two nice ones in the upper part of the chora, but I especially liked the kafeneio Karai, where we were also lucky to be able to watch a trio playing an excellent set one night (keep your eyes open for flyers and mini posters around the chora if you want to find good music).
The house is cozy: not huge but comfortable, beautifully appointed, clean, all we needed was there. It is ideal for 2 people, but it suited us perfectly with 2 young kids too. The view is right on to the sea and it's unforgettable: the balcony overlooks a long bay so you have the stretch of water in front of you, and the land beyond it.
The owner was not in Astypalea when we visited, but for keys etc. we met a friend of hers who was extremely friendly and helpful (she has a shop in the chora - don't miss it if you like quality souvenirs rather than the usual touristy stuff).
We have stayed in dozens of places in many trips to the Cyclades and the Dodecanese and we have no doubt this place is among our 2 or 3 favourites. We would definitely like to stay here again and would not hesitate in recommending it to friends. Avoid it only if you tend to like hotels more than private homes!
More island tips: 1) Maltezana has nice spots for bathing, and they are not too crowded; we liked Astakoukos and Almyra for food there. 2) If you tour the island by bus, like we did, you will probably find there are 2 buses taking turns on the same lines; the experience is definitely different on the 2 buses, try all you can to take at least one trip on Panagiotis' white bus, with 60s music and a huge pot of basil dangling from the rearview mirror as an air freshener.
