Martha's Vineyard Vacation Rentals in Chilmark

This remarkable single story home features a large living and dining room with post and beam cathedral ceilings. Floor to ceiling glass doors open onto the outdoor deck overlooking the gorgeous rolling meadows and trees. At the center of the home is the beautiful kitchen with ample work space for ...Read the full description.

Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a fully equipped kitchen, an...Read the full description.

This bright and cheerful, wooded retreat is truly tranquil, yet just a little over a mile from West Tisbury village where you have Alley's General Store, 7A Foods featuring take-out breakfast and lunch, the gas station, the West Tisbury library, the old Ag Hall where they have the Farmer's Market, A...Read the full description.

Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four bedroom, 2 bath home has an expans...Read the full description.

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 Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass ...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.

Gracefully situated atop the hills of Spring Point in Chilmark, the 4-BR (sleeps 8-10) home features panoramic water views sweeping from Gay Head Light to the Elisabeth Islands and east. This 4.750 sf family sanctuary was designed to balance inside and outside family gathering spots with private sp...Read the full description.