Where To Stay On Martha's Vineyard, MA - Howtobookyourtrip

A classic New England destination, Martha’s Vineyard is home to six towns spread across the bubbly Down-Island and placid Up-Island areas. The debate over the best base on the island has been going on for a long time and, frankly, won’t end any time soon.

To form your own opinion, we suggest you start with one of the two most popular towns: Edgartown or Oak Bluffs. Here, you’ll find lovely accommodations, fun vacation vibes and all the distractions you need for a good time.

Then, when you visit, make it a thing to explore every town on the island. If a different one than the one you chose turns out to be your favorite, that’s yet another reason to return to Martha’s Vineyard soon.

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Jump to

• Edgartown – Easternmost lodging
• Oak Bluffs – Playful town
• Vineyard Haven – Gateway hub
• Up-Island – Escape the crowds

Down-Island versus Up-Island

The third biggest island on the USA’s East Coast, Martha’s Vineyard comprises two primary regions: the eastern Down-Island and western Up-Island.

Edgartown, Oak Bluffs and Vineyard Haven are the lively towns of the Down-Island region. Filled with things to do, this is the best area to stay for visitors who want a quintessential experience.

Up-Island, home to the humble West Tisbury, Chilmark and Aquinnah, is a much quieter option. Offering unmatched solitude, Up-Island is for those who truly want to escape from it all.

What else?

Don’t let the fact that the Down-Island towns actually line up on the island’s northern coast confuse you. The designation is a remain of the whaling era — when heading west, you go up in longitude and vice versa.

Edgartown

A Down-Island gem and the easternmost town on the island, Edgartown is full of history. Marvel at its countless historic white-painted homes in Greek Revival style, many of which were built by ship captains in the 1800s when Edgartown was a whaling center. Completing the townscape, restaurants and shops lure you from one street corner to the next.

For some quality beach time, make acquaintance with Edgartown’s iconic beaches:

• Lighthouse Beach: The closest beach, Lighthouse Beach is a relaxing half-mile walk from the downtown area. Embrace soft sand, clear water and Edgartown Lighthouse’s stunning 360 views of the surroundings.
• Joseph Sylvia State Beach: Connecting Edgartown and Oak Bluffs, this Nantucket Sound stretch of coastline was a shooting location in the iconic “Jaws” blockbuster. Don’t miss to stop for photos at Jaws Bridge.
• South Beach: The seemingly endless South Beach faces the Atlantic Ocean, meaning the surf is rougher. Walk east or west from the access point, and it’s soon just you, the sun and the waves.

If you want additional seclusion, consider a day trip to Chappaquiddick Island, east of Edgartown. A short ferry ride (under 5 minutes) takes you there from Edgartown Harbor.

Is there anything negative about picking Edgartown? Well, the fancy setting can make the hotel rates steep. So, if traveling on a budget, you might find the other towns more appealing.

Pick Edgartown for: Timeless elegance.

Best hotels in Edgartown

Harbor View Hotel

Set between the downtown area and the beach, the upscale Harbor View Hotel offers jaw-dropping views of Edgartown Lighthouse. Top amenities, including a seasonal pool, ensure a stay as comfy as they come.

Book Harbor View Hotel

The Sydney

The Sydney features boutique accommodations spread across two buildings. The Main House is perfect for those who prefer a contemporary style, while the Captain’s House caters to history buffs. When hunger calls, grab a bite at the on-site L’Etoile.

Book The Sydney

The Christopher

Once the home of a ship captain, this eye-catching hotel welcomes you with a swaying American flag. Enter to find cozy rooms with bright coastal colors and appreciated common areas, such as a tranquil courtyard. For the best experience, book a room or suite with a balcony.

Book The Christopher

The Richard

Here’s a chic hotel right on Main Street, but still sheltered from noise, with prime access to shopping and dining. Built as a ship captain’s home in the 1800s, The Richard combines the best of old and new — property highlights include the relaxing garden and quintessential front porch.

Book The Richard

Oak Bluffs

Sandwiched between Edgartown and Vineyard Haven, Oak Bluffs stands out for its playfulness. Particularly during the summer season, the downtown area of Oak Bluffs brims with life.

The center of activity is Circuit Avenue, lined by shops, restaurants, bars and things to do for all ages. Go round and round on the iconic Flying Horses Carousel, the USA’s oldest platform carousel. Made in 1876, it first served Coney Island but has since 1884 been part of the quintessential Martha’s Vineyard experience.

Across Oak Bluffs, signature gingerbread cottages in vivid colors contribute to the fun vibe. Once built for camp meetings, over 300 colorful cottages dot the heart of Oak Bluffs, providing limitless photo opportunities.

When hunger calls, head to Martha’s Vineyard Chowder Company, which grabs the best-chowder-on-the-island title year after year. Still, maybe the hot lobster rolls served here are even better — try both.

A stone’s throw from the lively downtown area, the easily accessible Oak Bluffs beach calls for your attention. To have unlimited sand-between-your-toes opportunities, bed down at one of the hotels within steps of the beach.

Pick Oak Bluffs for: Playfulness.

Best hotels in Oak Bluffs

Summercamp

Want the most whimsical place to stay on Martha’s Vineyard? On an island so famous for its historic summer camps, this hotel brilliantly unites former campgoers (and children at heart). At the Summercamp, it’s hard to decide what’s best: the nostalgic decoration, pretty harbor view or position at the heart of Oak Bluffs.

Book Summercamp

Pequot Hotel

Only 500 feet (152 m) from the beach, Pequot Hotel features classic island architecture, complete with soothing porches. If you ever want to leave this peaceful scene, Circuit Avenue’s buzz is just minutes by foot away, too.

Book Pequot Hotel

The Oak Bluffs Inn

You can’t beat the Oak Bluffs Inn for access to Oak Bluffs entertainment. It sits directly on Circuit Avenue with restaurants and stores on its doorstep, yet has a tranquil home-away-from-home atmosphere.

Book The Oak Bluffs Inn

Vineyard Haven

The westernmost town in the Down-Island area, Vineyard Haven (also known as Tisbury) is the only town on Martha’s Vineyard with a year-round ferry service. Each month of the year, excited visitors arrive in Vineyard Haven from the mainland.

As one of the bigger towns on the island, Vineyard Haven is also home to a dynamic commercial district. On Main Street, you’ll find an appreciated selection of stores, restaurants and accommodations.

Does time stand still? At The Black Dog Tavern, it certainly feels like it. This wood-paneled institution serves tasty American fare against the backdrop of the stunning Vineyard Haven Harbor.

Although Vineyard Haven is such a practical town, many visitors fall for the unique appeal of Edgartown and Oak Bluffs instead. It can be a good thing: You often find cheaper hotels in Vineyard Haven.

Pick Vineyard Haven for: Convenience.

Best hotels in Vineyard Haven

Charles & Charles

Charles & Charles welcomes you with open arms and a rare attention to detail. Embrace a heartwarming bed and breakfast set on a flower-dotted Vineyard Haven property where the modern but homey rooms make it easier than ever to settle in. Best of it all? The delicious (and complimentary) poolside breakfast.

Book Charles & Charles

Up-Island

Away from the ferry connections with the mainland and main population centers, the Up-Island area comprises the rural towns of West Tisbury, Chilmark and Aquinnah. Here, you’ll find a limited selection of lodging, dining and things to do.

But that peacefulness is, actually, the big draw. Visitors come to the westernmost part of Martha’s Vineyard to kick back and enjoy mile after mile of empty beaches.

Pick Up-Island for: Seclusion.

You might wonder…

Which is the nicest part of Martha’s Vineyard?

The two main parts of Martha’s Vineyard offer very different experiences: Down-Island is the busier part of Martha’s Vineyard where the island’s three biggest towns are located, while Up-Island is more secluded with fewer things to do and thinner crowds.

Which is better: Edgartown or Oak Bluffs?

Edgartown is famous for its white-painted houses and Oak Bluffs for its colorful gingerbread cottages. Both towns certainly offer the comforts you crave for including quality lodging.

Which is better: Oak Bluffs or Vineyard Haven?

Oak Bluffs attracts visitors with its colorful cottages, iconic beach and lively Circuit Avenue. Vineyard Haven is the island’s main port of entry with superb restaurants and shops on Main Street. As it’s just a few miles between the two towns, you can easily go between them during you visit.

Are there any Martha’s Vineyard hotels on the beach?

Most hotels on Martha’s Vineyard are located close to a beach. A shining example is the peaceful Pequot Hotel, putting you within 500 feet of the beach.

Where to stay in Martha’s Vineyard with family?

With friendly, spacious suites and inviting rates (for Martha’s Vineyard), Charles & Charles is one of the best picks on Martha’s Vineyard for families. If you prefer a beach-adjacent location, consider the quirky Pequot Hotel.

Where do celebrities stay on Martha’s Vineyard?

Each summer, the rich and powerful go to Martha’s Vineyard to recharge. Some of the names on a very long list of celebrities spotted on the island include Oprah Winfrey, Bill Gates, the Clintons, Morgan Freeman, David Letterman and, of course, the Obamas.A known hot spot for the elite is the luxury Harbor View Hotel, brilliantly facing Edgartown Harbor. But you might as well run into a celebrity at Nancy’s restaurant in Oak Bluffs, a Mad Martha’s ice-cream shop or just about anywhere on the Massachusetts island.

Are there any hotels on Chappaquiddick Island?

There are no hotels on Chappaquiddick Island. You’ll find the hotels closest to Chappaquiddick Island in Edgartown, only a short ferry ride away.

More New England guides

• Best things do on the Vineyard
• When to visit the Vineyard
• Where to stay in Massachusetts

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