Category Archives: Chappaquiddick

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.

Chappaquiddick Exclusive: Martha’s Vineyard Vacation Rental

I get excited about all of my rentals because every property on Martha’s Vineyard offers something unique and surprising. But, sometimes I list houses that truly blow me away – this is definitely one of those houses. Note: this house is available for 1-2 weeks this August 2008 only!

When you arrive at this Chappy compound, you will not want to leave – and you won’t have to because everything you need is right there. Made for big groups and surrounded by fields and ocean, it’s the ultimate getaway.

Magnitude. Perfect for entertaining or for bringing the whole family, the property includes a charming guest house, and in total offers 6 bedrooms, 3 kitchens and 6.5 bathrooms, housing up to 12 people. Set on 20 acres, this Chappy property offers total privacy and stunning views of the surrounding landscape.

Amusement. Pool, tennis court, pristine Chappy beaches nearby, Master Suite & kitchen that open on to covered patios, porches & decks surrounding the house, a private 6 hole golf course next door and 20 secluded acres to explore…need I say more?


Habitation. The house is newly remodeled and includes a family room, study and a bow window perfect for reading and relaxing. This space invites a full house and pure festivity, while offering quiet places for Vineyard escape and serenity.

For more pictures, details or rental inquiries, email me at annemayhew@gmail.com or call 508-627-6070 x27.

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.