Planning a Vacation to Martha's Vineyard

The Cutest House on Martha’s Vineyard

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My first visit to Martha’s Vineyard was on a day trip from Rhode Island in 2011. My mom was obsessed with the idea of channeling her inner Kennedy, and SVV, my dad, two of their friends and I were all along for the ride.

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

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. Still, we had gloriously sunny weather and I immediately became enamored with the small Massachusetts island, which we toured for the day by bus.

Planning a Vacation to Martha's Vineyard

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.

Planning a Vacation to Martha's Vineyard

Enter: Alex in Wanderland.

It turns out my long-time pal’s mom Kathryn owns a house right in the center of the Campground at Oak Bluffs, which she lives in part of the year and rents 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

This time we were already in Massachusetts, however, and the drive out to the ferry spot from Boston, where we’d stayed the night before, was an easy 90 minutes by car.

The first thing you should know about planning a trip to Martha’s Vineyard is that you need to book your ferry quite far out if bringing a car, particularly in the summer months. Friends who have tried to plan similar trips lately were unable to do it because they couldn’t nab a spot on the coveted car ferry. If memory serves me correctly, Kathryn made our June reservation back in March.

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

The car ferry departs from Woods Hole 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 second thing you need to know about planning a trip to Martha’s Vineyard is that many 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

Alex’s family’s home is located right smack in the historic Martha’s Vineyard Campmeeting Association (MVCMA, 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

Being plagued with Peter Pan Syndrome—and the fact that I never had twin beds growing up—I immediately claimed what I like to think of as the “kids’ room.” Angie, our matriarch, took the master bedroom while Alex took the remaining queen bed on the other side of my quarters.

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 accommodations.

Planning a Vacation to Martha's Vineyard

Which brings me to third thing you need to know about planning a trip to Martha’s Vineyard will not come as any surprise now: Skip the idea of a hotel or B&B; you should definitely stay in one of the 300 homes in the Campground of Oak Bluffs, many of which are rented for part of the high season.

Planning a Vacation to Martha's Vineyard

Planning a Vacation to Martha's Vineyard

Alex’s mom rents hers out just six weeks out of the year—if you’re interested in booking with her, leave a comment below and I can put you in touch with her—and for a very reasonable price at that. It’s currently a three bedroom, one-and-a-half bathroom home, though she’s adding a master suite this fall, and I can’t wait to return and see the addition.

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

Because who doesn’t want to stay in a gingerbread dream home? I’m already counting down the days until my own family rents from her in summer 2017 (oh yes, that’s happening—you know us Lunas like to make our vacation plans early!).

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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COMMENTS
  • July 5, 2016

    amazing images in marthas vineyard thats very cute ..

  • July 5, 2016

    This looks like a great place! Is it close to the beach?!
    Cate recently posted..The Surf and Sun of MancoraMy Profile

  • July 5, 2016

    Those houses look too cute! Even on a dreary rainy day it would brighten up my spirits!
    Dominique recently posted..Ir.D.F. Woudagemaal – A UNESCO Heritage SiteMy Profile

  • July 5, 2016
    Kathryn Allen

    Kristin, Thanks for all the love! It was fabulous to finally meet you. Can’t wait to see your renovation magic in 2017…Here we come, Bonnaroo!

  • July 6, 2016

    Those are all Gorgeous homes!! Love them all 🙂 The alice in wonderland one is very neat.
    Tanya recently posted..The Best Times to Use an Employee Assessment in the Hiring Process My Profile

  • July 6, 2016

    gingerbread dream home, indeed! i want to go!
    mary @ minutes per mile recently posted..catching upMy Profile

  • July 8, 2016

    So stinkin’ cute! Seeing the 3 of you on the porch really gives it some scale – looks like you are on the porch of a dollhouse 🙂
    Leigh | Campfires & Concierges recently posted..Solo in SouthEast AsiaMy Profile

  • July 10, 2016

    I am so in love with your photos and I have been to Marthas Vineyard. It is like a little piece of paradise! Do you intend on going back?
    Steven Conte recently posted..How To Choose A Wakesurf BoardMy Profile

  • July 11, 2016
    Ris

    These pictures are just stunning! Kristin, you are so talented 🙂

  • July 13, 2016
    Briel K.

    OMG could those houses be any cuter?! Yet another place to add to my list!

  • July 17, 2016

    I want this house – totally adorable! Perfect for a month in the winter!
    Andi recently posted..8 Years!My Profile

  • January 6, 2017
    Charlotte Pillow

    My husband and I are planning a trip to Martha’s Vineyard and would love to rent this home. You mentioned that you could connect us to the owner if I left a comment. Please connect us. Thanks.

    • January 9, 2017

      Hi Charlotte! I forwarded her your email. If you don’t hear from her, feel free to contact me (CamelsAndChocolate AT gmail) =)

  • January 8, 2017

    I’m planning a trip to Boston, (my first time in the US!) soon and I will definitely include Martha’s Vineyard in my itinerary. The pictures are oh so lovely!!
    Grace @ Sandier Pastures recently posted..Where we stayed: Movenpick Resort & Spa Tala Bay Aqaba, JordanMy Profile

    • January 9, 2017

      Ahh, what a fun trip! Where else will you go while you’re over this way? Nashville? 😉

      • January 15, 2017

        I just looked up Google maps (and Expedia) and wow…Nashville is at least 5 hours from Boston!! It’s like going to a different country. But one day, I’m going to get there and see you and your beautiful house (and cute dogs!)
        Grace @ Sandier Pastures recently posted..Where we stayed: Movenpick Resort & Spa Tala Bay Aqaba, JordanMy Profile

        • January 15, 2017

          Ha! I was kind of just kidding, but obviously would be fun to have you here! What kind of transportation gave you five hours, out of curiosity? It would take you an hour to fly or maybe 14 hours to drive. I actually just looks as I’m going this summer and I can fly to Boston for $49 each way. So cheap, that’s crazy!

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