Pineapple Inn

This place is terribly run. For the three days I was there, I didn’t see one manager, and I was «checked in» by a piece of paper on the mantel. The smoke detector was hanging open in my room, which was almost exactly the size of the bed (just a tiny bit of room to walk around the bed).
I almost never give bad (or any) Unilocal reviews – the only reason I’m doing so for this place is because of this: there was ice cold air pouring in through a ceiling grate that had a broken handle. I smelled cigarette smoke at first, and then was just cold, so I emailed both the innkeeper and the reservation manager. On the check in sheet, it explicitly said to email with any concerns. Neither of them responded, and the problem was not addressed. If I had received an email, I would not have written this.
I needed a place for the weekend, and neither of the other two inns I’ve stayed in were available, so I found this online. It’s true that this is cheap for Nantucket, but it’s actually not cheap for what you get (which is not much), and now I see why there was last minute availability during the high season. I could also hear every single word spoken in both the courtyard and in the rooms/​hallway next to mine.

We booked here because it was one of the last rooms available on short notice. It does the trick if you just need a place to sleep while enjoying Nantucket. Not a place where you hang out and enjoy the amenities. The best «perk» is the shuttle to and use of the pool area at Summer House in Sconset.
The worst part of our stay was sleeping on the king-​sized taco in room 2. You both end up rolling into the sizable low spot in the center of the mattress.
The rate was reasonable for Nantucket.

You stay here because you want the door to door shuttle to Sconset Summer House, lets face it. Other than that, it is like any other B&B in ACK, except that it makes some promises that it doesn’t completely deliver. For example, it is affiliated with some of the higher end restaurants in the area and claims that this affilition a) makes their continental breakfast and cappuccinos something to enjoy and linger over b) makes it easier to get reservations at these places and they will be «happy» to assist you in doing so. Now, a continental breakfast is basically just muffins so thats kind of the same anywhere. I did see a cappucino maker but it was never once in use – and the muffins were either not put out until an hour into breakfast time, or were too few for everyone. As far as dinner reservations, we were «assisted» in getting them, but FAR from happily.
So my advice is if you want happy, helpful staff – this isn’t your place. If you just want to be able to easily get to Sconset and use the pool, etc there, then it is totally fine.
Also, as a side note, we took the shuttle to Sconset one day that it POURED so we went to the Summer House restaurant across the street (not the one on the beach obviously). They did not offer to send the shuttle to go back to town until its usual time (3 hours later), or offer any coffee/​hot chocolate or basically anything to pass the time until then but instead directed people to the other restaurant – OUTSIDE in the pouring rain – with a straight face. Not very hospitable considering you are in the hospitality industry.