This was my first time saying in Carlton's home as an AirBnB guest, though my family rented the house many summers from his family throughout my childhood in the 90s. Back then, it felt like a fairy tale, and although I've grown up, I am happy to say it was as wonderful as I remembered!
The house is needless to say gorgeous, a landmark of 19th century Victorian cottage design with a fascinating history. Its been remodeled since my youth and looks fantastic - with a new kitchen and bath - but retains its original flair.
You are in the center of Oak Bluffs - probably the most lively of Martha's Vineyard towns - with close access (3 min walk) to Circuit Ave's best restaurants, bars, and shops (much frequented by the Clintons and the Obamas.) The Black Dog and Mnemsha Blues are island staples, if its your first time here, but my favorite shops include Third World Trading, the Book Den East, Slight Indulgence, and Tuckernuck Antiques. Its also nice to be near conveniences that are harder to find in the quieter up-island towns (grocery store, hardware store, library, gas stations, liquor stores, bike rentals, yoga studio). Its very close to the Oak Bluffs ferry (10 min walk, 2 min drive) which is especially important if you come over without a car - and the local town beaches (Oak Bluffs TB - 10 min walk; East Chop and State Beach -15-20 walk). Vineyard Haven and Edgartown are only a short bus ride away. And Carlton's lovely mother-in-law lives on island year-round and is readily accessible should you need anything.
Favorites include the Flying Horses (a must for the kids), Mocha Motts (coffee and bagels), Linda Jeans (packed ever since the Clintons visited 20 years ago), Giordano's (Italian family style restaurant and B.O.'s favorite fried clams), Nancy's upstairs and its spectacular harbor views, Ben & Bills (ice cream), two historic small movie theaters (which are increasingly rare in the U.S.), the campground cottages, and in August, the OB Fireworks. If you have a chance, participate in the Campgrounds activities over the summer (Illumination, concerts and lectures, flea market, yoga-in-the-park, and the over-100-year-old tradition of the Community Sing).
In short, highly recommended and I hope to stay again soon!