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Escape to a breezy room at the Beach Plum Inn, which also happens to have one of the island's best restaurants.
(Photo: Gabriela Herman) |
Check into the Dockside Inn (from $109), a boutique bringing a dose of cheeky wit (a recent sign for walk-in guests offered rates “lower than the Kardashians’ IQ ... combined”) to the gingerbread village otherwise known as Oak Bluffs. Bright, modern rooms offer views of the harbor, sleep up to five, and are just steps from the Oak Bluffs ferry dock. The hotel offers a few unique spins on service: A platinum 1956 Rolls Royce Silver Cloud (with driver) is on hand to shuttle you around the island; an on-call virtual concierge answers guests' questions on where to find the best lobster roll, bowl of chowder, or cocktail via text; and warm cookies are served every afternoon.
Escape down a dirt path to the Beach Plum Inn (from $195 in September; $145 in October, reservations recommended), a small cluster of hotel rooms and cottages seemingly suspended in a cloud of hydrangeas overlooking Menemsha Harbor. Each of the airy rooms is elegantly simple, with crisp linens and comfy couches, and several have Whirlpool tubs or lovely porches perfect for curling up with a novel. Ask for Evelyn's House, a two-bedroom cottage that sleeps six and has one of the prettiest views of the water. The on-site restaurant, run by 12th-generation islander and Babbo-trained chef Chris Fischer, is one of the Vineyard’s finest, and much of the seasonal bounty on the menu—think bass and lobster served with fennel fronds ($35); or a goose, pork, and bean cassoulet ($32)--comes straight from Fischer’s nearby Beetlebung Farm. The dining room has just been given a full rustic-chic revamp, and Fischer’s recently hosted a series of pop-up dinners with world-class chefs like Paul Lang from A Casa and Ari Taymor of L.A’s Alma.
Revel in the old-school maritime splendor of Harbor View Hotel (from $210 in September; $175 in October), a showstopper comprised of a mix of plush hotel rooms, cottages, and suites that’s been playing host to guests since 1891. Situated on Starbuck’s Neck, the spit of land on the edge of Edgartown that’s also home to a series of whaling captain’s mansions, the hotel’s sightline of the Edgartown Lighthouse is bar-none. Grab a half-dozen Honeysuckle oysters and a microbrew at Henry’s Bar (whose Tartan rugs seem plucked from The Official Preppy Handbook), then snag a turquoise rocking chair on their wraparound porch to take in the view.