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Chappy Waterfront Rentals

 Chappaquiddick Island is the easternmost point of Martha's Vineyard, connected to the main island by only a very narrow barrier beach. Ferries escort passengers to and from the main island, making living on beautiful Chappaquiddick easy. While the whole island boasts exceptional real estate, the real gems are its waterfront rentals. Choose from views of the Edgartown Inner Harbor, Katama Bay, or uninterrupted ocean. Enjoy the views from a private beach, dock, or from your large entertaining deck. Whether you rent on a waterfront home on Chappy for a family vacation, romantic getaway, or to simply live the island life for a summer, we have just the rental to make you feel right at home.

Scroll down to view all current listings of Chappy waterfront rental homes. If you have questions, contact Sandpiper Rentals today.  You might also like to browse all Chappy rentals.

 

You may search for your vacation accommodations here. We have offered you several ways to search and locate your accommodations below.

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21 properties found

3046 Bed / 4.0 Bath / Sleeps 16

Chappaquiddick

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Vintage Chappaquiddick home on Martha's Vineyard at the Snows Point. This 5 bedroom Main house overlooks Katama Bay with...read more

3054 Bed / 3.0 Bath / Sleeps 11

Chappaquiddick

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Chappaquiddick Rental, Enjoy spectacular views of both Edgartown Inner Harbor and Nantucket Sound from this charming wat...read more

3094 Bed / 4.5 Bath / Sleeps 8

Chappaquiddick

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Stunning Chappy opportunity! Lovely home on Edgartown Harbor with private dock and incredible water views. A rare oppo...read more

3107 Bed / 6.0 Bath / Sleeps 13

Chappaquiddick

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A captivating marriage of structure and surrounding yields an absolute masterpiece of Eco-conscoius modern architecture ...read more

3133 Bed / 1.5 Bath / Sleeps 6

Chappaquiddick

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Martha's Vineyard vacation Cottage by the sea. Located on the south side of Chappaquiddick island, it is adjacent to the...read more

3165 Bed / 4.0 Bath / Sleeps 10

Chappaquiddick

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Ocean all around! This is the perfect Chappy retreat for your family vacation this summer. Stunning views from almost ...read more

3175 Bed / 4.0 Bath / Sleeps 10

Chappaquiddick

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An architectural dream come true, built as a labor of love in 1969 then renovated in 2012! Beautifully sited on a bluff ...read more

3334 Bed / 3.0 Bath / Sleeps 7

Chappaquiddick

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Martha's Vineyard rental on Chappaquiddick Island. This contemporary home on Katama Bay has unobstructed views. Great po...read more

3355 Bed / 4.0 Bath / Sleeps 12

Chappaquiddick

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Martha's Vineyard vacation rental on Chappaquiddick Island. Wonderful rustic old Chappy Cottage. Property fronts Katama ...read more

3374 Bed / 3.0 Bath / Sleeps 8

Chappaquiddick

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Chappaquiddick Island, Martha's Vineyard Rental. Charming beach cottage looking out onto amazing view of Edgartown outer...read more