Chappaquiddick
Chappaquiddick, commonly referred to as Chappy, is a small island (about 5 miles long x 3 miles wide) off the eastern end of Edgartown. The mainland of Edgartown and Chappy are sometimes connected, along their southern coast, by a narrow barrier beach only accessible by 4-wheel drive vehicles. The southeastern point of this beach is called Wasque Point – a popular fishing spot especially during the annual Martha's Vineyard Striped Bass and Bluefish Derby held each fall. Chappy boasts numerous wildlife preserves and pristine beaches and offers a more remote, slower pace of life, and yet is just minutes from Edgartown Village. With no commercial center or stores, when one needs or wants to go into town, a bargelike ferry called the On Time shuttles up to three cars, passengers and cyclists to and from the Village. If you feel Chappy checks all the boxes for your summer vacation location, we have a large inventory of homes that includes quaint camps to large waterfront estates.
55 properties available
Chappaquiddick on Martha's Vineyard, amazing single level cottage lovingly renovated to make your stay more comfortable and enjoyable. Updated appliances in the kitchen, ac mini splits and heat units in all three bedrooms and living room. A comfortable living room and screened porch to relax and unwind. Great location, just one mile from My Toi, Di
Edgartown Chappaquiddick 323
Chappaquiddick on Martha's Vineyard, amazing single level cottage lovingly renovated to make your stay more comfortable and enjoyable. Updated applian... Read More
Chappaquiddick on Martha's Vineyard, amazing single level cottage lovingly renovated to make your stay more comfortable and enjoyable. Updated applian... Read More
Set along the shores of Chappaquiddick, this remarkable estate seamlessly blends privacy and elegance with direct access to the water. At the heart of the property lies an impressive 140-foot deep-water dock, complemented by a stunning five-bedroom main house and a charming three-bedroom guesthouse, making it an ideal venue for both leisure and ent
Edgartown Chappaquiddick 337
Set along the shores of Chappaquiddick, this remarkable estate seamlessly blends privacy and elegance with direct access to the water. At the heart of... Read More
Set along the shores of Chappaquiddick, this remarkable estate seamlessly blends privacy and elegance with direct access to the water. At the heart of... Read More
Enjoy lovely summer days at this contemporary Chappy home. The reverse level layout takes full advantage of of the inner harbor views with the kitchen, living, dining, sun porch and open deck on the upper level. The sun porch is the perfect spot to enjoy a cup of coffee in the morning or reading a book in the afternoon. You will find three spacious
Edgartown Chappaquiddick 375
Enjoy lovely summer days at this contemporary Chappy home. The reverse level layout takes full advantage of of the inner harbor views with the kitchen... Read More
Enjoy lovely summer days at this contemporary Chappy home. The reverse level layout takes full advantage of of the inner harbor views with the kitchen... Read More
 Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story home features central air, an inviting swimming pool, and ocean views. Enjoy the spacious elegance and bright living spaces in the main house, featuring an en suite bedroom conveniently located on the
Edgartown Chappaquiddick 300
 Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story h... Read More
 Discover the ultimate 5-bedroom retreat, where luxury and relaxation converge to redefine your vacation experience. This top-of-the-line, two-story h... Read More
Three-bedroom Chappy property with front porch and distant views of Katama Bay and South beach. Private setting with a large outdoor deck area for relaxing and entertaining. All three queen bedrooms on the second floor of the main house and detached guesthouse joined by an outdoor deck includes a family room, game room area and extra sleeping accom
Edgartown Chappaquiddick 303
Three-bedroom Chappy property with front porch and distant views of Katama Bay and South beach. Private setting with a large outdoor deck area for rel... Read More
Three-bedroom Chappy property with front porch and distant views of Katama Bay and South beach. Private setting with a large outdoor deck area for rel... Read More
Piece of heaven on Chappy. You will enjoy this property from the moment you enter with a grand view of Katama Bay right from the entrance. Beautifully furnished reverse level home with peaked ceilings and open space maximizes this stunning location. Views from kitchen, living and dining out to a substantial deck is made for entertaining and loun
Edgartown Chappaquiddick 397
Piece of heaven on Chappy. You will enjoy this property from the moment you enter with a grand view of Katama Bay right from the entrance. Beautiful... Read More
Piece of heaven on Chappy. You will enjoy this property from the moment you enter with a grand view of Katama Bay right from the entrance. Beautiful... Read More
A classic reverse-style contemporary with peeks of Katama Bay from the widows walk. The living area is open and airy with high ceilings and there is plenty of outdoor space - screened porch, deck and patio - to feel the essence of the beach. Three bedrooms on first floor share one full and one half baths. Just down the road from the calm waters of
Edgartown Chappaquiddick 373
A classic reverse-style contemporary with peeks of Katama Bay from the widows walk. The living area is open and airy with high ceilings and there is p... Read More
A classic reverse-style contemporary with peeks of Katama Bay from the widows walk. The living area is open and airy with high ceilings and there is p... Read More
Charming Chappy boathouse rental with views of Edgartown outer harbor. Reminiscent of seasons past, with updated kitchen and baths, this adorable three-bedroom cottage provides all the comforts in a perfect location to enjoy your Martha's Vineyard vacation. Main bedroom located on the first floor and the two twin bedrooms on the second floor. The
Edgartown Chappaquiddick 449
Charming Chappy boathouse rental with views of Edgartown outer harbor. Reminiscent of seasons past, with updated kitchen and baths, this adorable thr... Read More
Charming Chappy boathouse rental with views of Edgartown outer harbor. Reminiscent of seasons past, with updated kitchen and baths, this adorable thr... Read More
This charming three-bedroom cottage features an open kitchen, dining, and living area. On the first floor, two bedrooms have access to a shared hall bathroom. The second floor boasts a spacious king suite complete with a private bath. Both the king bedroom and the living area are equipped with AC mini-split units for added comfort. The cottage is l
Edgartown Chappaquiddick 407
This charming three-bedroom cottage features an open kitchen, dining, and living area. On the first floor, two bedrooms have access to a shared hall b... Read More
This charming three-bedroom cottage features an open kitchen, dining, and living area. On the first floor, two bedrooms have access to a shared hall b... Read More
Less than a mile from the Quammox Preserve beach, this charming two-bedroom home on Chappaquiddick, built in 2018, offers a bright and inviting open-concept layout. The modern kitchen and dining area flow seamlessly into the living room and onto a spacious outdoor porch—perfect for relaxed island living. The main level features a primary en suite b
Edgartown Chappaquiddick 491
Less than a mile from the Quammox Preserve beach, this charming two-bedroom home on Chappaquiddick, built in 2018, offers a bright and inviting open-c... Read More
Less than a mile from the Quammox Preserve beach, this charming two-bedroom home on Chappaquiddick, built in 2018, offers a bright and inviting open-c... Read More
Spectacular 180 degree views, set up high overlooking Cape Pogue. This three bedroom pet friendly single level home with wonderful views. Features an open kitchen, living and dining area with sliders that open out to an outdoor deck. An added bonus of two of the three bedrooms offering gorgeous water views. Additional sleeping with a queen bed lo
Edgartown Chappaquiddick 408
Spectacular 180 degree views, set up high overlooking Cape Pogue. This three bedroom pet friendly single level home with wonderful views. Features an ... Read More
Spectacular 180 degree views, set up high overlooking Cape Pogue. This three bedroom pet friendly single level home with wonderful views. Features an ... Read More
Set back among mature trees on Chappaquiddick, this classic Cape-style home offers comfortable space for a traditional island week. With 4 bedrooms and 2 bathrooms accommodating up to 10 guests, the layout works well for extended family stays or shared summer rentals in a quiet location near the ferry.
Enter into the welcoming living room, which co
Edgartown Chappaquiddick 342
Set back among mature trees on Chappaquiddick, this classic Cape-style home offers comfortable space for a traditional island week. With 4 bedrooms an... Read More
Set back among mature trees on Chappaquiddick, this classic Cape-style home offers comfortable space for a traditional island week. With 4 bedrooms an... Read More
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