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286 Chilmark

Bedrooms: 4
Bathrooms: 2.5
Accommodates: 8
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Description

Tastefully furnished and adorned with antiques and fine art, this upscale summer retreat in Chilmark offers classic Vineyard charm with modern comfort. An original Yankee Barn tucked just off South Road, the home is designed for effortless summer living and entertaining.

The dramatic post-and-beam architecture showcases a sun-filled cathedral living room bathed in southern light. Sliders open to a spacious wrap-around deck, complete with teak chaise lounges and dining tables—perfect for al fresco gatherings after a day in the sun. The charming, well-equipped kitchen flows easily into a traditional dining room, while a cozy loft provides a relaxed space for watching movies or curling up with a good book.

Four gracious bedrooms offer comfortable accommodations, with conveniently located bathrooms ensuring ease for family and guests alike. After a beach day, rinse off in the outdoor shower before settling in for a Vineyard evening.

Ideally situated just minutes from the pristine shores of Lucy Vincent Beach, Menemsha Beach, and Squibnocket Beach, this exceptional Chilmark home offers the perfect blend of privacy, elegance, and coastal lifestyle.

Mini-split a/c units in the living room and all bedrooms.
2 Smart TV's with streaming. No cable.

Room Details

Bedrooms:
1st Floor Queen w/ensuite bath
2nd Floor Queen
2nd Floor Queen
2nd Floor 2 Twins
Bathrooms:
1st Floor Shower & Tub ensuite
1st Floor 1/2 Bath
2nd Floor Shower

Beds

  • Queen 3
  • Twin 2

Amenities

Entertainment

  • Games
  • High Speed Internet
  • Wireless Internet
  • TV

Kitchen

  • Refrigerator
  • Coffee Maker
  • Ice Maker
  • Microwave
  • Toaster
  • Blender
  • Wine Glasses
  • Lobster Pot
  • Dishwasher

Outdoor

  • Deck
  • Gas Grill
  • Outside Shower

Indoor

  • Air Conditioning
  • Linens
  • Washer & Dryer
  • Ironing Board
  • Towels
  • Iron
  • Fans
  • Vacuum
  • Dryer

Rates

DatesNightlyWeekly
06/27/2026 - 07/03/2026$929$6,503
07/04/2026 - 07/10/2026$929$6,503
07/11/2026 - 07/17/2026$929$6,503
07/18/2026 - 07/24/2026$929$6,503
07/25/2026 - 07/31/2026$929$6,503
08/01/2026 - 08/07/2026$1,000$7,000
08/08/2026 - 08/14/2026$929$6,503
08/15/2026 - 08/21/2026$929$6,503
08/22/2026 - 08/28/2026$929$6,503
08/29/2026 - 09/04/2026$814$5,698
09/05/2026 - 09/11/2026$814$5,698
09/12/2026 - 09/18/2026$814$5,698
09/19/2026 - 09/25/2026$814$5,698

Availability

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