Martha's Vineyard Vacation Rentals in Chilmark

Come experience the rest and relaxation of slowing down in this adorable well appointed and air conditioned family home in the heart of Chilmark surrounded by rolling fields and beautiful stone walls. Tucked back off Middle Road, this four bedroom two bath rental comes with linens and towels, high ...Read the full description.

Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely...Read the full description.

Just a short distance from the iconic Chilmark Store, this newly remodeled home features three bedrooms and 2.5 baths, blending high-end finishes with a relaxed, beachy island aesthetic. The thoughtful layout begins on the first floor with a spacious primary suite featuring an en-suite bath for ulti...Read the full description.

Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as...Read the full description.