Be My Guest: Accommodations on The Vineyard

By Sheryl Wesley
EMVY Managing Partner / Contributor

Please Be My Guest!

Over the past several decades, Martha’s Vineyard has become a summer playground for politicians (the Obamas and Clintons for example) and celebrities alike (is that Larry David?). But it also continues to be a destination for the rest of us!

If there is anything any seasoned visitor knows about Martha’s Vineyard, it is ‘Get your ferry reservations and accommodations ASAP!’

Ready for a relaxing getaway and wondering where to find the best places to stay on Martha’s Vineyard? Be my guest and read on!  We’ve got you covered!

On the Vineyard, sites for online room-rental and accommodations have become an alternative to hotels, motels, and traditional B&B’s.

Whether you’re looking for a luxurious private home that sleeps 10 or are ballin’ on a budget – you can find it all on Martha’s Vineyard.

With more than a plethora of lodging options, there are no shortage of choices. Because there are no chain hotels, each accommodation location gives you that authentic Island experience.

Here are my top reasons to book with an online accommodations resource vs Hotels:

Online hospitality services gives you the opportunity to rent an entire home or even a room in a shared space and pay by the night, rather than per person. This usually works out a lot cheaper for big groups that can sometimes translate to lower prices than hotels in the area. However, on Martha’s Vineyard, you will find it challenging to rent a whole home for less than five consecutive days the least.

You will find with most Bread & Breakfast services a more intimate reception in that the hosts are warm and attentive, the continental breakfast are great to start your day, and the locations are usually closer to town or your desired location.

There are a few questions you must ask before deciding whether to stay in a hotel or a popular vacation rental site. Who are you with? Where are you going and what do you want to get out of your trip?

When most stay in hotels, they want luxury. You will most likely not only pay for the comfort and location but pay for the service. This includes for the most part the 24/7 check in, housekeeping and toiletries to name a few.

A stay on Martha’s Vineyard is usually about pressing the reset button and unwinding, so hotels may be secondary to this purpose.

Be My Guest 2.png

Top reasons to stay in a hotel vs accommodation sharing:

•            All the amenities are at hand and if they’re not, there’s someone to help you just a short phone call away.

•            Hotels are usually situated in perfect locations for sightseeing, business meetings and of course the restaurants and bars.

•            They’re seemingly the better alternative when travelling with children. Whether it’s a kid’s club service you need, extra sheets in the early hours of the morning, a set up crib on arrival or even a theme park on site. Hotels make sure that your comfort and entertainment are well taken care of.

•            Everything is guaranteed with hotels (although nothing is really guaranteed in life, am I right?). You know exactly what you’re going to get when you walk in and how you’re supposed to leave it. It’s the familiar feeling most like to have when traveling.

•            Of course, all of this comes at a price and depending on the location of your trip, staying at a hotel can compromise a budget quite easily. So if it’s the cheaper alternative you’re looking for or you’re traveling in a bigger group – hotels may not be the ideal option for you.


Why you might want to stay in a home exchange vs hotels:

Online accommodation services have a huge database of places to stay, whether you fancied renting a beach bungalow by Inkwell Beach, a Gingerbread Cottage in Oak Bluffs or a 7 bedroom home with a pool in Edgartown or Vineyard Haven, they’ve pretty much got you covered.

•            Having your own space (possibly a full-stocked kitchen, living room, etc.) also provides you with a lot more freedom to relax, enjoy each-other’s company, invite friends over, and of course cater for yourself.

•            With a home-stay option you shouldn’t expect any amenities or services and with a cleaning fee added on at the end of every booking – you definitely do not receive a turn down service. This can sometimes translate to lower prices than hotels in the area.

Be My Guest 1.png


Whatever source for sleep you choose, it’s always good to take note of some insider tips:

•         If a hotel stay is more your vibe, boutique hotels, which are very trendy now on Martha’s Vineyard tend to be a little cheaper. So do some extra research for travelers seeking a whimsical alternative to the island’s old-school inns. 

•         Also, join the local Social Media platform ‘The Inkwell’ to score unpublished accommodations posted by the owner(s) directly.

•         This is for the ‘in-the-know’, but there are owners that rent out rooms in their private homes for 1-3 days at a time for the least.  This is usually by a word-of-mouth find. 

If you are the outdoorsy type where you just use your accommodations to sleep, there is also a hostel on the Island where you’ll meet travelers from around the world. The hostel is open during high season which is from May to October so make your reservation today if this is your thing. There are also campground options if you want to throw up a tent or bring your sleeper camper!

Clearly, the choices and possibilities for travel and living are endless. Whatever it is you are looking for, you are likely to find the perfect place to make your Martha’s Vineyard experience exactly what you want it to be.

If you are a patron of preference, please see our link

Be My Guest Aquinnah.png


Lay of the Land

At just 100 square miles, the Vineyard is split between down-island and up-island towns.

Down Island

Edgartown: Stately homes of 18th-century whaling captains line the streets of this historic town.

Oak Bluffs: Known for its Victorian cottages and ice cream/fudge shops, this is the island’s tourist hub.

Vineyard Haven: Come here for one-off boutiques and the main ferry terminal.

Up Island

Aquinnah: Make the trek to this western town for its colorful clay cliffs and Gay Head Lighthouse.

Chilmark: Islanders escape the summer crowds for the quiet fishing villages along Chilmark’s coastline.

West Tisbury: The most bucolic area has acres of rolling farmland.


Getting Around

Martha’s Vineyard has an airport. Catch a ferry from Massachusetts, New York, or Rhode Island. If you don’t bring your car, rent a bicycle or a moped. Taxis, Ubers and Lyfts are also plentiful.


No matter the season, no matter the reason, no matter your budget - there's a Martha’s Vineyard experience waiting for you!