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Don't miss the boat to Martha's Vineyard

Escapes Under $500
by , SmarterTravel Staff
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Martha's Vineyard beachfront house (Photo: Robert Schellhammer)
Editor's Note: This story was originally published on March 29, 2007. To see the most recent SmarterTravel articles on related topics, please click on any of the following links: Anne Banas, beach, destination, Escapes Under $500, HomeAway, island, Martha's Vineyard, summer, vacation rental, VRBO, weekend getaways.

If you want the perfect Martha's Vineyard vacation, start planning early—really early. Otherwise, as I discovered, you just might miss the boat. Here are some ways to ensure you get the trip of your dreams hassle free, while saving at least enough money for another Black Dog sweatshirt. You'll be off the ferry and steaming fresh seafood in no time. Quahogs anyone?

Last year, I was completely prepared for my August stay on the Vineyard well in advance, or so I thought.

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Getting to the Vineyard

Six weeks before my trip, I scrambled to make a reservation with the Steamship Authority, the single ferry that carries cars, only to get stuck with undesirable departure times. At first, I couldn't get the days I needed, so I had to sweat out the wait list, which barely came through at the very last minute.

Hoping to correct my mistake this year, I set out to book in mid-February, six whole months in advance, but the same thing happened. That's when I learned that car reservations for nonresidents opened up January 17 and sold out within weeks for peak times such as weekends and the month of August.

Word of advice: Know your plans and book early. Or, forget the car.

Bringing a car is not only difficult, but also expensive and ultimately unnecessary. While it costs $130 round-trip for the car during the peak summer months, foot passengers never need reservations, and pay fares starting at only $14, depending on the ferry company. For those who need to go the long haul once on the Vineyard, there's affordable bus service and even taxis. Perhaps the best mode is bicycle, which you can bring on the ferry for about $6 or rent. Taking it slow—pedaling by rolling horse farms, "honor-system" flower stands, and even homespun studios along the new Arts & Artisan trail—is the only way to live in true island style.

Vacation rental

Unfortunately, vacation homes are not exempt from the book-early mentality. According to Abby Rabinovitz, a rental agent at Tea Lane Associates in West Tisbury and Chilmark, "This year has been a hot season and some of the best homes were booked up by January 1." She says, "If you know your plans in advance, it's best to start looking in September and October."

However, if you're late in the game, don't despair. "The market is always in flux, where owners are always putting new properties on the market. The early spring can be an especially good time to find deals if your plans are flexible."

Rabinovitz continues, "To save some money or get a nicer place, look outside August, the peak month. July, late June, and early September are particularly good times for equally pleasant weather and lower prices." Or, as she suggests, "Rent a home that's a bit off the beaten path in places like Aquinnah instead of Chilmark." I found a hidden cottage in the West Tisbury woods near the airport for only $1,500 per week in August. Comparable places on the island cost between $2,000 and $3,500.

Prices will depend on what features—such as size, quality, and location—you prefer, so it's best to shop around. Also, as a rule of thumb, homes right on the beach tend to cost more.

Good websites to find rentals include Martha's Vineyard Online, a comprehensive source dedicated to the Vineyard, as well as multi-destination sites such as VRBO, HomeAway, and CyberRentals, which all allow you to search by town. If you're having trouble finding availability, try calling a local agent who works directly with multiple property owners.

Affordable activities off the beaten path

Booking transportation or a rental home can make or break a vacation, but what you do on the island can create the best memories. While many congregate in the popular towns of Edgartown, Oak Bluffs, and Vineyard Haven, heading "up island" to the countryside will take you out of the fray. And, you won't need to plan in advance or spend a thing.

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