Category Archives: Chilmark

When Should You Book Your Vineyard Vacation?

Pool with view of Sengekontacket PondOn Martha’s Vineyard, we begin booking rental homes for the following season before the current one ends!  Many families decide they like coming to the island every year for a least one week.  If they like the rental property they are staying in, and know they will be back, it makes sense for them to commit to the same house while they are here.

Vineyard Haven Beach Frontage

Rental home bookings continue through the fall and right up until the beginning of the season.  Critical things to consider when trying to decide when to book your vacation home:

  • Most owners know whether their repeat tenants are coming back by the end of September.  If you are a new tenant or looking to change houses it may be difficult to get a commitment prior to that.
  • Steamship Authority (vehicle ferry) opens up ticket sales for the summer months around mid January.  Tickets sell out quickly for the weekend turnover days during the season.
  • January is a strong booking month because of the ferry ticket sales and many popular houses will book up quickly.
  • Rental homes are listed through out the season, to a certain degree, making last minutes bookings a strong possibility.

Sunset in Aquinnah

All in all, you should consider booking your Martha’s Vineyard vacation home ahead of time, especially, if you have specific criteria, price and dates in mind.  If you can be somewhat flexible, any time is a good time!  We have a house for you with over 500 listings in our inventory.

Do NOT Miss Chilmark Chocolates

Chilmark Chocolates is one of those places on the island that you just have to go. The chocolate is amazing – original recipes either handmade or hand-dipped. And the atmosphere is inspired and inspiring.

The shop, located in the heart of Chilmark, is staffed by disabled people. With equipment that has been adapted for ease of use and specific abilities, the entire staff fills the store with must-have truffles, chocolate covered fruit and more. Delighting our taste buds while raising awareness – what more could we ask for?

While the Butter Crunch is a longtime favorite, Chilmark Chocolates dips seasonal and local treats in their chocolate (think strawberries, blueberries and cranberries) for tastes that are truly Vineyard grown.

Where to Shop for Food on Martha’s Vineyard

As you plan your vacation on Martha’s Vineyard, your mind is, most likely, already lying on the beach – probably not shopping at the grocery store. But one of the greatest benefits of renting a house on the island is that you don’t have to dine out for all of your meals or rely on hotel restaurant hours. Your house comes equipped with a complete kitchen – so you can eat your lobsters whenever you like.

Here’s where to shop for groceries:

Down Island
Stop and Shop (Vineyard Haven and Edgartown)
Two convenient locations for this good old, standard supermarket, includes a large organic/natural section and features competitive prices.

Cronig’s Market (Vineyard Haven)
A Vineyard landmark with everything you need. Cronig’s has a great organic/natural section, supports the Island Grown Initiative (Buy Local!) and carries many local items – food and body care. Healthy Additions, found in a separate building to the left of the main store, is stocked with natural snacks, health and beauty products.

Reliable Market (Oak Bluffs)
Classic family store in its 3rd generation, known for its great meat and fantastic butcher and conveniently located in the heart of Oak Bluffs on Circuit Ave.

Katama General Store (Edgartown)
A perfect stop on the way to the beach with groceries, a deli and even catering services.

The Chappy Store (Chappaquiddick)
Right on the main road, about 2 miles from the ferry. Just the basics and sandwiches for the beach.

Up Island
Up Island Cronig’s (West Tisbury)
Smaller version of the Vineyard Haven store conveniently located in West Tisbury – perfect for up-island renters who choose to stay on the quiet side of the island. Up Island Cronig’s has everything you need.

Fiddlehead Farm (West Tisbury)
Great produce, much of it organic, and tasty specialty items with a european flare like crackers, cheeses, sausages and sauces.

Alley’s General Store (West Tisbury)
Right in the heart of town, basic groceries plus all the old-fashioned general store amenities and charm including toys, games and beach fare.

West Tisbury Farmer’s Market (West Tisbury)
Not a ‘store’ in the classic sense, but offering an incredible spread of island grown produce, meats, baked goods, infamous vietnamese springrolls, medicinals and crafts every Saturday and Wednesday all summer. Don’t miss it!

The Chilmark Store (Chilmark)
Staple groceries and goods attached to an island-renowned pizzeria and deli. Pull up a rocker on the front porch and watch life at Beetlebung Corner float by.

Menemsha Market (Menemsha)
Small, quaint and full of little treasures, just like Menemsha. Goods for the beach and books for kids included. Perfect for the groceries and pie when you are all the way up-island.

Tea Lane Caterers & The Phantom Chef (Chilmark)
If you don’t feel like cooking, don’t have time to get to the market or you’re planning a party, call Chef Dee Smith, the Phantom Chef. The food is amazing and the gourmet drop-off meal service is the perfect compliment to your Vineyard vacation.