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Book a Stay in the Cutest Neighborhood on Martha’s Vineyard

Hoca

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Planning a Vacation to Martha's Vineyard
My first visit to Martha’s Vineyard was on a day trip from Rhode Island many moons ago. My mom was obsessed with the idea of channeling her inner Kennedy, and SVV, my dad, some friends and I were all along for the ride. At the time, I oohed and ahhed over the houses, mentally bookmarking where to stay in Martha’s Vineyard if ever I got back to this charming island.



Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard


This post was last updated in May 2024.

How to get to Martha’s Vineyard​


We took a very rocky passenger ferry over from Providence, and I spent the duration of it paying homage to the porcelain gods (tempestuous seas and my sensitive stomach have never been agreeable companions). It was not the best way to start off the day. If you’re in Boston and don’t have time to stay overnight, you can book a day trip to Martha’s Vineyard and see the highlights.

Planning a Vacation to Martha's Vineyard

Still, we had gloriously sunny weather and I immediately became enamored with the small Massachusetts island, which we toured for the day by bus. It was charming, it was picturesque, it was not anywhere in a million years I ever thought I’d get the opportunity to visit on an overnight vacation.

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Where to stay on Martha’s Vineyard​


It turns out my long-time pal Alex’s late mom Kathryn owned a gorgeous Vineyard house right in the center of the Campground at Oak Bluffs, which Alex and her sister rent out for six weeks each summer. She was kind enough to let Alex, Angie and me to invade her lovely home for a long weekend—a long weekend that would prove to be not nearly enough time to do all the eating and drinking and seeing we hoped to accomplish.

Planning a Vacation to Martha's Vineyard

Alex’s family’s home is located right smack in the historic Martha’s Vineyard Campmeeting Association—aka “the Campground”—just minutes from downtown Oak Bluffs. The tight streets aren’t ideal for driving, so most residents get around by foot. They also all know one another, having been neighbors for years, often decades, and are extremely welcoming of tourists like myself.

Planning a Vacation to Martha's Vineyard

From the moment we pulled up to the 1870 masterpiece, I was bowled over by its beauty. Alex’s mom and her boyfriend had spent the past couple years restoring this old lady to her rightful state; as someone who also is in the midst of renovating a 19th century home, I can doubly appreciate the time and care—and, OK, money—that such a project entails.

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard


Every single room had such character, many remnants of historic memorabilia and so many perfect vignettes that Kathryn pieced together in the most Pinterest-worthy cottage I’ve ever had the pleasure of staying in.

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard
Planning a Vacation to Martha's Vineyard

It was basically like being at summer camp for a weekend, only my cabin mates weren’t strangers and we were in the Four Seasons of rental homes.

Planning a Vacation to Martha's Vineyard

Which brings me to first thing you need to know about planning a trip to Martha’s Vineyard will not come as any surprise now: There are hotels in Martha’s Vineyard and, specifically, boutiques B&Bs near Oak Bluffs—I went to Summercamp, for example, just to check it out, and it’s truly dreamy. Here are some other cool hotels in Oak Bluff and Edgartown:


If you do have the opportunity, though, you should try and book one of the 300 homes in Oak Bluffs’ Campgrounds, but residents are limited to renting them out just six weeks a year and, as such, they often go very quickly.

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

More tips on planning a trip to Martha’s Vineyard​


The first thing you should do—well, after sorting your lodging—in planning a trip to Martha’s Vineyard is booking a car ferry if bringing a car, particularly in the summer months. Friends who have tried to plan similar Martha’s Vineyard trips lately were unable to do it because they couldn’t nab a spot on the coveted car ferry. Our June reservation was made back in March.

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

You can also book a day trip to the Vineyard and be untethered from the car situation.

The car ferry departs from Woods Hole on mainland Massachusetts and was very speedy and smooth, the opposite of our experience traveling over from Rhode Island. We had just enough time to go up top, order a Coke and check out the entry into Oak Bluffs before it was time to climb back into our cars and pull out of the ferry terminal.

Planning a Vacation to Martha's Vineyard

The next thing you need to know about planning a trip to Martha’s Vineyard is that a lot of places are cash-only. So if you’re a credit card-heavy traveler like me, stock up on cash at your preferred ATM before you arrive on the island, or else get it in Oak Bluffs before you start your trip. You’ll be glad you took my advice, trust me, as oftentimes the three of us were emptying our wallets trying to scrape up enough bills to pay for our meals.

Planning a Vacation to Martha's Vineyard
Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard





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Where to Stay on Martha's Vineyard, Massachusetts

Where to Stay on Martha's Vineyard, Massachusetts
 
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