Where To Stay on Martha's Vineyard, Massachusetts, for a Local Experience

Edgar Hotel Martha’s Vineyard is about a mile (1.6km) away from Edgartown’s bustling harbourfront – a location that puts you in the heart of the island’s Portuguese-American community and its largest town. Outdoor enthusiasts will love relaxing like a local with walks through the Mass Audubon’s Felix Neck Wildlife Sanctuary and Manuel F Correllus State Forest. If you desire a coastal stroll, let the concierge direct you to the secluded Sheriff’s Meadow Sanctuary.

Prefer exploration on four wheels and without a guide? Then, you’ll love seeking out hole-in-the-wall pubs, back-alley boutiques and the best-kept local secrets of Martha’s Vineyard behind the wheel of a Mercedes-Benz. The Harbor View Hotel lends these complimentary vehicles to guests for day trips around the island. While you could cruise over to the Jaws Bridge (which appeared in the 1975 movie Jaws), we suggest scooting south for unspoiled ocean views from the serene Chapeda Hill.

One of the best ways to explore Martha’s Vineyard like a local is on a bicycle, and it just so happens that a stay at the Kelley House Hotel includes complimentary bike rentals. Such a lovely amenity is made all the more special with the hotel’s instant access to the 44 miles (70km) of biking trails on the island. Hop on the short South Beach Route, explore the woods on the State Forest Loops, or pedal through Edgartown to Oak Bluffs or West Tisbury, all accessible from your suite.

Spend one summer on Martha’s Vineyard, and you’ll see why vacationers keep coming back. Spend the off-season here, however, and you’ll see why locals fell in love with their home. Hotel Ginger offers laid-back lodging in the colder months, though its on-property activities don’t cool down. Rosé wine tastings and weekend pop-ups highlight the best of Martha’s Vineyard, giving you the opportunity to learn more about local life from the comfort of this Victorian boutique hotel.

Don’t let the private guest-only beach at the Vineyard Harbor Motel trick you into believing you’ll be rubbing elbows with tourists alone. You’re in an excellent location to easily engage with locals during the many annual film festivals held at nearby Tisbury Market. If you’re not in town between May and October, when the Martha’s Vineyard Film Society screens the latest flicks, year-round film and live theater productions will get you acquainted with the island’s diverse arts and culture.

The historic waterfront district in Edgartown is a hotbed of activity and a cultural epicenter on Martha’s Vineyard, thanks in part to its many art galleries. Vineyard Square Hotel & Suites helps art lovers draw up a full schedule of gallery hopping without tracing more than two blocks. The Winter Street Gallery, Edgartown Art Gallery, Eisenhauer Gallery, Martha’s Vineyard Art Association and other cozy galleries are all within a paintbrush’s throw.

Whether your drink is strong because of caffeine, sugar or hard liquor, you’ll find the best local beverages right around the corner from the Richard. Local favorites include fruit-forward cocktails at Alchemy and one of the best wine selections in the world, as ranked by Wine Spectator magazine, which can be found at Atria. On the coffee front, Espresso Love has you covered. Should you bring back a local bottle of wine from MV Wine & Spirits, there are corkscrews and wine glasses waiting in your room.

Not only does Summercamp Hotel keep you in the heart of the laid-back Oak Bluffs village, but the staff here are also happy to help you explore Martha’s Vineyard by land and sea via unique experiences. Hit the water on a paddleboat or via a kayak tour. When you return to the hotel, sign up for the Lark Hotels Instagram Scavenger Hunt, which will lead you to some of the coolest local places in the OB (and can potentially knock a few bucks off of your bill).

The chill island-time vibes of the Christopher are so relaxing that you’ll want to lounge in the courtyard all day. Whenever your appetite stirs you from your slumber, you’ll be happy to know that some of the best local restaurants on Martha’s Vineyard are less than a mile’s walk away. Handmade tagliatelle pasta at the Terrace, lobster potstickers at Atria and black mission figs stuffed with blue cheese at Lucky Hank’s are among the many mouthwatering dishes that the Christopher puts you close to.

Winnetu Oceanside Resort won’t try to convince you which season on Martha’s Vineyard is best, but it will tempt you to stay until fall to experience the hotel’s best-kept secret: second summer. This is the season to enjoy an intimate day trip to Katama Bay with the owners of Signature Oyster Farm. This exclusive private tour will guide you around the farm, where you’ll learn to shuck and savor local oysters. It’s a BYOB excursion, so be sure to ask Winnetu staff which bottle of Martha’s vino pairs best with this seafood.