Martha's Vineyard, Massachusetts
Harbor View Hotel
What it is
A Martha’s Vineyard mainstay since 1891, with modern-meets-Victorian interiors; charming cottages; and a heated saltwater pool.
What it isn't
Landlocked. Guests have access to loaner Mercedes Benz’s and cruiser bicycles (complete with wicker baskets, natch) for free-wheeling around the island.
What we think
You know a hotel is good when the entire cast and crew of a Hollywood blockbuster checks in (in this case: Richard Dreyfuss, a mechanical shark named Bruce, and everyone else involved in filming 1975’s “Jaws”). The grande dame of Edgartown is still a star, thanks to plentiful fun activities on-site—including croquet by the fire pits, a cabana-lined outdoor pool, and a veranda stocked with rocking chairs that were seemingly tailor-made for sipping bellinis. Each guest room is indulgently appointed with Frette linens, cozy robes, and Molton Brown toiletries, but we’d recommend booking a Captain’s Cottage for a private outdoor shower, kitchenette, and gas fireplace at-the-ready for curling up for a movie night a la Dreyfuss himself.
You're here because
You practically require a pool bar, or it’s not a vacation. That this one, the Roxy, happens to serve lobster flatbread pizza is just a bonus.
You’ve had your share of over the top hotel breakfasts, but something about Bettini’s feels like it’s gone to another level of greatness. Settled in your tufted red leather banquette peeping out on the water, you order an only-in-Maine brunch: Maine duck trap wild smoked salmon lox for your bagel, and blueberry buttermilk pancakes with cultured maple butter and whipped creme fraiche. Edible heaven.
Right on the waterfront alongside Lighthouse Beach, just a mile stroll from the Martha’s Vineyard Museum, where permanent exhibitions include an 1854 Fresnel lighthouse lens with 1,000 crystal prisms.