10 Amazing Home Rentals on Martha's Vineyard

Martha's Vineyard, known by the locals as simply, "The Vineyard," is the 58th largest island in the United States and the third largest island on the East Coast. It is also one of the most sought after vacation spots for celebs and the affluent looking for an upscale summer haven. The Vineyard is considered a summer colony and getting there is no easy job. It is only accessible by boat or air, yet still, the summer population has continued to grow as well as the number of year-round residents. Perhaps this is due to the fact that the streets have been walked by American royalty such as the Kennedys, Clintons and Obamas, making it not only a summer paradise, but a place rich with American history.

It is not only political personalities who have brought Martha's Vineyard the notoriety it now enjoys. In 1974, Steven Spielberg filmed the iconic classic, Jaws in one of the small fishing villages there and used many locals in the film. Beloved comedian John Belushi is buried there and his grave is a popular site for visitors to the island. Other celebrities who have been known to frequent The Vineyard include Carly Simon, David Letterman, Diane Sawyer and author Judy Blume. Although some consider this summer place a "mini Hollywood", the locals tend to be protective of the celebrities who come to this island for peace and anonymity.

Martha's Vineyard is made up of six towns, with Edgartown being the largest and Tisbury being the main point of entry. Oak Bluffs has a busy night life and Chilmark is one of the more picturesque including the fishing village of Menemsha. Though this is one of the most beautiful areas in the United States, it is certainly not one of the cheapest. Housing prices are 96% higher than the national average, and as you will see from the list below, even renting will cost you a pretty penny. Below are some very exclusive vacation homes available for rent on The Vineyard. Prices quoted are based on a seven night stay.


10 556 Chappaquonsett, Vineyard Haven: $12,000

This home is located on the north shore of the island, allowing you peace and quiet on your own secluded beach. A private waterfront compound, this 22 acre property is perfect for the large family reunion or family celebration. This is a large home with over 5,700 square feet, and boasts eleven bedrooms and seven baths and is designed so that there is a breath taking water view from every room in the house. This property includes three structures, the main house, a large guest house which is a renovated carriage house, and a pond house that all have expansive water views.

9 55 Jewett Lane, Vineyard Haven: $16,000


This beautiful seaside vacation home is steeped in history and folklore. Built in 1758 it was originally a tavern where sailors would come for a respite from the harsh realities of sea life. It is now an elegant home with six bedrooms and four baths, a library, formal dining room and living room with fireplace. Less than 25 feet from the water, the path and stairway that lead you there include an enclosed outdoor shower. This home includes a key to Hancock Beach, an exclusive, gated south shore beach and can also be rented with a neighboring guest house to enable you to include more friends and family in this once in a lifetime vacation.

8 61 Oldfield's Path, Chilmark: $16,500

This home has more of a contemporary feel and offers five bedrooms, four in the main house and one in the guesthouse, and six baths. With an open floor plan and exposed beams, this house is friendly and open with fabulous water views. The living room leads onto a screened in porch and deck that overlooks Tisbury Great Pond. This rental comes with some very nice features including a key to private Quansoo Beach, four kayaks and of course the obligatory lobster pot where you can cook up steaming lobsters to serve in your expansive dining room that easily seats twelve.

7 2 Osprey Lane, Chilmark: $18,000


2 Osprey Lane, offers clean lines and sunlit rooms throughout the entire home. This is a five bedroom, five bath home, located just a short walk away from Chilmark Pond. This is the perfect home for families with younger children as the fenced in yard and pool area allows for private and safe enjoyment. This home is finished with many high end decorative touches and rental includes several kayaks making it just a short paddle to Barrier Beach.

6 31 Tower Hill Road, Edgartown: $20,000

This gorgeous home is filled with old world charm and is just exactly what one pictures when they think of Martha's Vineyard. Overlooking the harbor, this house has kitchen walls covered with bead board paneling and the cupboards are lined with charming blue and white dinnerware. This rental is very unique in that it has over 5o feet of private beach and a deep water dock. It also has two beachfront outbuildings, The Boathouse and The Playhouse, both with shower facilities. Make reservations early for this one as it has been a huge favorite year after year.

5 11 Half Inch Lane, Chilmark: $22,000


With superbly clean lines and a European flair this home is efficient, modern and at the same time, comfortable. With five bedrooms and four baths, there is plenty of room to accommodate family and friends with private areas and common rooms for gathering. Enjoy awe inspiring views from the decks and expansive windows on the water side of the home. This home also has an in-ground pool and outdoor shower and is just a short walk to the beach.

4 69 Cape Higgon Way, Chilmark: $35,000

This is a brand new home that combines clean contemporary with rustic charm. This house has six bedrooms, with five of them on the main level with expansive water views, and six baths. In certain rooms, the home appears to be floating on the ocean, due to the 180 degree water view that is truly a rare find. The main living room has a wet bar and leads directly out to the deck. A detached bed and bath are just a few steps away from the main house, offering privacy and seclusion to guests who so desire. Combine these features with the fact that the above price includes beach chairs and a cooler and you truly have a week in paradise!


3 61 Naushon Rd, West Tisbury: $45,000


This exquisite home offers astounding views of the Atlantic, Elizabeth Islands and Woods Hole from Martha's Vineyard. This large home sleeps twelve comfortably with seven bedrooms and six baths. 61 Naushon rd has many desirable amenities such as private beach access, pool, outdoor kitchen and walking trails along the cliffs overlooking the beach. This home offers the best of both worlds with privacy being a main component while the center of town is just a ten minute walk away.

2 1 Plantingfield Way, Edgartown: $50,000

Though this home was built in the eighteenth century, it is in perfect condition with some modern additions and all the comfort we have come to expect from luxury vacation homes. For the price listed above, one should expect nothing less! This waterfront estate is nestled on its own private beach overlooking Nantucket Sound and is situated at the end of a secluded country lane. The main house and guest house provide a total of eleven bedrooms (ten with water views) and eight baths with over 6,700 square feet of living space. There is an outdoor shower with a spacious changing room overlooking the water and a four car garage. Top that off with a sixteen by 34 foot swimming pool and an outdoor kitchen and dining area and you are truly in the lap of luxury.

1 58 Oyster Watcha Road, Edgartown: $60,000


It doesn't get any better than this over the top, luxurious 10,000 plus square foot waterfront compound. This house has direct access to over half a mile of  sandy coastline, including a beach so exclusive and private that the last two acting presidents have made repeat visits to it's sandy shores. The property also includes a six bedroom main house and a gorgeous two bedroom guest house with 180 degree water views. The kitchen is a chef's dream and there is a soaring solarium, a fully stocked wine cellar with attached billiards room and a gym and steam room. Perhaps you would enjoy spending time in the 50 foot solar heated pool equipped with underwater sound system while enjoying a beverage from your fully stocked bar. This estate also has organic orchards and vine covered loggias for beautiful outdoor dining. 58 Oyster Watcha Road has been featured in Architectural Digest and is truly one of a kind.


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