Private, luxurious location on Tisbury Great Pond complete with Quansoo beach key. Vacation in Chilmark on the Pristine Shores of Tisbury Great Pond. This brand new home and guest house offers all the modern amentities.  Learn more...

Private house and guest house with heated pool and private association beach.  Learn more...

Masterfully designed home with an abundance of privacy. Perfectly situated for weddings and events or a peaceful holiday. Horse stable, barn and riding rink also available. Conceirge service available as well! Property is Entirely Wheelchair Accessible.  Learn more...

Nearly every room in this house and guest house boasts an unbeatable view of the North or South Shores of Chilmark from atop Blacksmith Valley.  Learn more...

Recently renovated four bedroom home situated on the Squibnocket Pond and steps away from Squibnocket beach. Included in this rental is an additional studio that has two twin beds and is literally a few feet from the waters edge.  Learn more...

Immaculate, elegant beach home to suit your every vacation need. Lush lanscaped gardens and decks for outside enjoyment. Large living spaces and a state of the art kitchen for days spent in.  Learn more...

Spacious 4000 square foot, four bedroom home with salt water pool and waterviews of Quitsa, Menemsha, Squibnocket, and Atlantic Ocean!  Learn more...

Classic beach house with long sandy beach. Bright, beautiful beach house with detached bunk house.  Learn more...

Spend your holiday in this quaint downtown summer home with unexpected privacy. Tucked away on a dead end road yet just moments away from Main Street and all downtown Edgartown has to offer.  Learn more...

Impeccable residence on the north side of downtown Edgartown. Delight in this in-town location, only steps to Fuller Street beach, Edgartown Light, and all that downtown has to offer.  Learn more...