Stayed for a week with my husband in Adegas do Pico and had a wonderful time. The cottage we stayed in was very well equipped with cooking utensils etc, and the rooms were comfortable and of a good size. But the main thing - the view. Oh my goodness, it was stunning! Every evening we would sit outside and relax just looking at the beautiful view of the ocean and the surrounding countryside. You do need a car if you're going to stay here as there's not much within walking distance (just a bakery and a pizza snack-bar basically) but you're best getting a car anyway, as there's some wonderful countryside on the island to explore.
The lady that showed us the property (the owner, as I believe the person who normally manages things was away that day) was very helpful and friendly and gave us lots of recommendations for places to eat etc. The only slight downside was that the 'manual' left in the cottage said that housekeeping would come by every 3 days to change towels etc but we did not receive any visits during our 7-night stay. Not sure if this was maybe a communication mix-up, and it wasn't a huge deal, but it did mean that our bins did not get emptied, and we actually ran out of toilet paper on our last day!
The house also seemed to have a family of cats (1 momma and 5 kittens) who hung around a lot which I loved, and they would come and greet us every time we approached the house. Am sure if you didn't like cats they'd soon make themselves scarce, but for me it was just an added bonus :)
All in all, a wonderful stay, and I wouldn't hesitate to go back!