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.
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.
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.
Enter: Alex in Wanderland.
It turns out my long-time pal’s mom Kathryn owns a gorgeous Vineyard 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.
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.
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.
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.
You can now book a stay in this Martha’s Vineyard cottage, too
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.
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.
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.
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.
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.
Updated in November 2020: Kathryn passed away in 2019 after a 15-month battle with brain cancer. Alex and her sister have resumed care of the house. If you’d consider booking your stay on Martha’s Vineyard with them, you’ll enable them to cover the cost of upkeep for such a special property that meant so much to their mom.
amazing images in marthas vineyard thats very cute ..
This looks like a great place! Is it close to the beach?!
Those houses look too cute! Even on a dreary rainy day it would brighten up my spirits!
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!
Those are all Gorgeous homes!! Love them all 🙂 The alice in wonderland one is very neat.
gingerbread dream home, indeed! i want to go!
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 🙂
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?
These pictures are just stunning! Kristin, you are so talented 🙂
OMG could those houses be any cuter?! Yet another place to add to my list!
I want this house – totally adorable! Perfect for a month in the winter!
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.
Hi Charlotte! I forwarded her your email. If you don’t hear from her, feel free to contact me (CamelsAndChocolate AT gmail) =)
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!!
Ahh, what a fun trip! Where else will you go while you’re over this way? Nashville? 😉
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!)
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!
Whoops!! I must have seen the flights with some layover somewhere! Yeah, it’s not 5 hours, sorry!
$49 each way is so cheap!!
Curious to know how much this gingerbread house is rented for? I’m looking to surprise my husband and though this sounds way too big for two people I’d like to explore the idea 🙂
So I’m a little young (I’m 12) but your friend Alex’s mom Kathryn bought the cottage from my parents and we stay there every summer! The pictures you took are wonderful ❤️ We drive all the way from Nova Scotia Canada 🇨🇦
My family stays there and I think it’s 1400 for a week
A group of friends are planning a trip to Martha’s Vineyard in Sept 2018. I would love to check into renting this house. Please forward information concerning it. Thanks so much.
love this post! great photos. could you please send me the contact info for your friends rental. it looks lovely. we are visiting this summer and am currently checking out rentals:)
thanks so much
I am Interested in renting on the vineyard. Love the photos and all the I formation you shared.
Availability for summer 2020
So sorry to hear of Kathryn’s passing. She clearly had a great vision and passion for her home. I’m so glad her family will continue on with the tradition. Can you please forward along my information to them should they continue to offer their house up for renting. Enjoyed your article!
What sad news about Kathryn. The way you described your experience was endearing and gave us a glimpse of who she was.
Do you know if there is availability in June or July 2021? There are 4 ladies traveling together. Are the accommodations adequate for us? What is the cost?
Hi Kate! They did finally add the property to Airbnb here: https://www.airbnb.com/associates/199892?s=67&c=.pi115.pk0_9&a4ptk=15799_0_9_199892&af=115
Absolutely in love with the blog. I am visiting Boston this weekend and your just confirmed my visit to Martha Vineyards.
Have a great time in Massachusetts, Vishu!
For all who have asked, here’s the booking link to the Martha’s Vineyard cottage: https://bit.ly/2HXsASt
Would like to know availability