I came here with my wife and infant for a long weekend on the island.
Really lovely, very unique space - superbly decorated loft nestled only a few short blocks (5 min) stroll from the middle of town (Circuit Ave, the cottages, the ferry, etc.), it is close to the Oak Bluffs hub bub without the noise. Also a very convenient point about the location - it is only a block away from Tony's Market which has good breakfast burritos and all your usual snacks for a night in if you so choose including the best french onion dip (Helluva Good brand, of course). Private parking is included and you can get anywhere in the island in less than an hour really from here.
Annie is super nice and you can just tell the space was done with her professional eye - a plethora of little chic touches. Very clean, it's the kind of space that just makes you feel relaxed and cool but also invigorated.
Stroll down the block to eat at Skinny's Fat Sandwiches (the Oak Bluffs location is open I think later than the Edgartown one), do a larger grocery run at Reliable Market, shop at Vineyard Vines, do the carousel, or eat dinner at Lookout Tavern - it's all very close. Of all the towns I think Oak Bluffs has the best mix although all the towns have their own thing or two. If you are looking to sit out in the sun there is plenty of beach, from this location if you have a car it's not an issue, but if not you may want to consider hopping on a vehicle of some sort and save the small hike to say Seaview Ave or further.