The Mansions of Vineyard Haven on Martha’s Vineyard

People today can enjoy the celebrity lifestyle by renting the kind of homes that they once marveled at on television, and they can live like a rock star for a week or two for about the same price as a decent hotel.

Those who are old enough to remember the 1980s will likely recall the television show “Lifestyles of the Rich and Famous.” Each week, Robin Leach visited the homes of Hollywood stars, professional athletes and business tycoons to give the audience a glimpse into the pampered lives of the wealthy. The show may have been pure escapism, but it left viewers pining for a lifestyle that would almost certainly remain beyond their reach.

That was almost four decades ago, and a lot has changed since then. People today can enjoy the celebrity lifestyle by renting the kind of homes that they once marveled at on television, and they can live like a rock star for a week or two for about the same price as a decent hotel. If you want to rub shoulders with A-listers and former presidents in one of America’s most exclusive vacation destinations, read on.

Living the High Life

The ultra-rich are not like the rest of us. They do not worry about the petty inconveniences that torment regular people because they have an army of assistants, advisors and servants to take care of mundane tasks like home and vehicle maintenance, and they are waited on hand and foot whenever they venture out of their luxury compounds.

Vacationers who want a taste of this lifestyle have traditionally visited luxury hotels, but now there is a better option. People who stay at hotels are always aware that they are guests, and they often feel out of place and uncomfortable. Vacationers who rent opulent mansions have a very different experience because they have the freedom to live as they please with no judging eyes to worry about, which is precisely the kind of day-to-day living that the ultra-wealthy enjoy.

If you would prefer to feel more like an owner than a guest, you may want to consider renting a luxury home for your next vacation instead of booking a room at a hotel. Spend a week or two living like a celebrity who does not have a care in the world, and feel free to enjoy your precious time off however you see fit with no rules to follow or schedules to keep. You can get up whenever you want to and do whatever you please, and you will be treated like a millionaire wherever you go. If you want to enjoy this kind of vacation experience, the toughest decision you will make is deciding which part of the country to visit.

Martha’s Vineyard

Thought to be named after a British explorer’s daughter, Martha’s Vineyard has been a popular summer destination for America’s wealthy elite for more than a century. The small island off the coast of Massachusetts has less than 17,000 permanent residents, but that number swells to more than 100,000 during the peak vacation season. Most of these visitors book rooms at hotels and guest houses scattered around the island, but the rich prefer to spend their downtime in luxury mansions.

Some of these wealthy visitors are so enamored with Martha’s Vineyard that they decide to buy properties on the island, and being savvy, they frequently rent these residences out when they are not using them. This gives vacationers the opportunity to enjoy a more exclusive experience. It also allows them to spend a week or two feeling like a resident rather than a visitor.

Famous people that call Martha’s Vineyard home include Michael J. Fox, Spike Lee, Diane Sawyer and Barak and Michelle Obama, and hundreds more A-listers that visit the island each year. They flock to the Martha's Vineyard because the residents are very discrete and treat them like royalty, and now you can live in the same homes they do and enjoy the same kind of treatment. But which town in Martha's Vineyard has the Best Luxury Vacation Rentals?

Vineyard Haven

Exclusive luxury homes on Martha’s Vineyard can be found in and around the quaint harbor town of Tisbury. The center of the village is so picturesque that it is called Vineyard Haven. The area is packed with things to see and do, and there is even a working alpaca farm nearby.

When visiting Vineyard Haven, you’ll see streets are filled with artisans offering handcrafted goods that you will not find anywhere else. The village’s renowned cultural district is only about a 15-minute walk from its docks and shipyards, so getting around could not be easier. Here are just some of the amazing attractions you can visit in Vineyard Haven:

  • The Vineyard Haven Harbor Cultural District: Starting at the village’s pristine harbor and stretching for about a mile, the Vineyard Harbor Cultural District features a library, playhouse, theater and film center. Visitors can also take in the Williams Street Historic District, which is included in the National Register of Historic Places. In addition, there is Martha's Vineyard Museum, which is one of the Vineyard’s most important cultural assets and a huge draw for visitors and locals alike.
  • Shipyards: Vineyard Haven is among the last remaining ports in the country that still build wooden ships. If you decide to visit the village’s harbor and shipyards, you will see carpenters and craftsmen displaying skills that may soon be lost forever. There are also two Class B tall ships to marvel at, and you can even take an excursion on a two-master schooner.
  • The West Tisbury Farmers Market: The hardships of the Great Depression prompted farmers on Martha’s Vineyard to found the West Tisbury Farmers Market in 1934, and the popular attraction was revived in 1974 by a group of local residents. The market is open on Wednesdays and Saturdays, and it is filled with some of the tastiest and freshest produce in New England.
  • The Black Dog Tavern: A sea captain who was dissatisfied with the lack of dining options in Vineyard Haven established the the Black Dog Tavern in 1969. The restaurant is now one of the most popular destinations in the area because of its amazing food, friendly service and island vibe. The captain named his restaurant after his loyal canine companion, and he created his menu by asking local residents to share their favorite recipes with him.

Luxury Rentals

Seacoast Properties has some of the luxury homes for rent in Vineyard Haven. You can find quaint country cottages and impressive estates on our website, and you will probably be surprised by how affordable they all are. Here is just a small selection of the luxury residences that you could call home on your next Martha's Vineyard vacation.


Located next to the West Chop Lighthouse, Lightside is a luxury seven-bedroom home with majestic and unobstructed views of Vineyard Sound. The home is an impressive 4,218 square feet, and its deck features an outdoor shower and BBQ grill. Spend a quiet day in your vacation retreat watching yachts, ferries and sailing ships, and then spend the evening curled up in front of a romantic fireplace.

Gorgeous Beach Cottage

If you are looking for an authentic island experience, you should consider the rustic beach house we have available right on the water. You could relax and unwind on a quiet sandy beach outside the front door, or you could go clamming at nearby Lake Tashimoo. Viewing the sunset from this remarkable property is an experience you will not soon forget, and its open-plan layout and cheerful decor will make you feel right at home.

A Slice of History

If you are drawn to Martha’s Vineyard by the area's culture and history, an incredible 18th-century residence overlooking Vineyard Haven’s picturesque harbor could be the perfect place to stay. The home features original architectural details, a huge front porch and a Steinway grand piano, and there is also a sandy beach that you can have all to yourself. The village is just a short walk away, and the views of the harbor are spectacular.

Contemporary Luxury

Visitors who plan to play a few rounds of golf while on vacation should consider this amazing four-bedroom residence in West Chop. The home has a private heated in-ground swimming pool, and it is located just a short walk from Mink Meadows Public Golf Course. The luxury residence features beautifully landscaped grounds and several living areas so everybody can relax, and it even has a detached two-bedroom guest cottage.

An Unforgettable Vacation Experience

The team at MV Seacoast Properties knows Martha’s Vineyard like few others, and they will do everything they can to ensure that your vacation in this magical part of the country is truly unforgettable. Our dedicated professionals will help you to find the perfect luxury rental, and they could also give you tips about the best places to visit, eat and shop. If spending your next vacation on Martha’s Vineyard living like a celebrity sounds good to you and you would like to know more, you can reach us by calling (508) 627-9201 or filling out our online form.