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Vacation Rentals in Chilmark

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5 Acre Privacy, Key to Black Point Beach- – Property 120243

  • Chilmark rental - house, 4 bedrooms, sleeps 8, beach, rural, washing machine
  • $2,500 - $4,250/week
  • Calendar Last Updated On: Aug 13, 2008
This contemporary architectural gem is shaped as a partial arc, allowing maximum privacy. On the ground floor are all 4 bedrooms, the dining room, the kitchen, and 2...

Chilmark Cottage and studio, 5 acre privacy, wireless internet – Property 120447

  • Chilmark rental - cottage, 3 bedrooms, sleeps 6, 1 bathroom, 1 half bath, near the ocean, rural, washing machine
  • $1,350 - $2,350/week
  • Calendar Last Updated On: Aug 13, 2008
This sunny Chilmark cottage offers total privacy on your own 5 acres. Located off a small private road, we are near to the Chilmark Store, the library, and the...

Desirable Chilmark Location Sweeping Ocean Views Private Beach – Property 194085

  • Chilmark rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, beach, near the ocean, washing machine
  • $3,000/week
  • Calendar Last Updated On: Jul 24, 2008
Enjoy panoramic views of Vineyard Sound & secluded association beach from this contemporary home with open floor plan. Groomed walking trails, association tennis, 5...

Private Air-Conditioned Retreat with water views – Property 133117

  • Chilmark rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, near the ocean, rural, air-conditioning
  • $2,000 - $3,600/week
  • Calendar Last Updated On: Jul 22, 2008
With a distant sweeping waterview, full privacy, and a total renovation, this property offers accommodations well above the norm.

Waterview, Private, Newly Renovated Tri-Level – Property 121220

  • Chilmark rental - house, 4 bedrooms, sleeps 9, 3 bathrooms, near the ocean, rural, washing machine
  • Calendar Last Updated On: Jul 22, 2008
This charmingly renovated home offers water views and a very large private yard. There are 3 levels; the upper level consisting of the master bedroom with a full...

Spacious, Conveniently Located Saltbox in Chilmark - – Property 106032

  • Chilmark rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, near the ocean, rural, washing machine
  • Calendar Last Updated On: Jul 14, 2008
This spacious, comfortably furnished home is conveniently located between Chilmark and West Tisbury. The master bedroom and a bath are downstairs; three bedrooms and...

Secluded Natural Chilmark House – Property 117303

  • Chilmark rental - house, 2 bedrooms, sleeps 8, 1 bathroom, near the ocean, rural, washing machine
  • $475 - $1,500/week
  • Calendar Last Updated On: Jul 13, 2008
Located at end of a dead-end dirt road on 1.5 acres with tall pines and oaks. Modified saltbox, owner designed & built in 1978 for potential active solar.

Classic Chilmark Home --Six Bedrooms, Sunny Deck, Can Accommodate Two Families – Property 162857

  • Chilmark rental - house, 6 bedrooms, sleeps 12, 2 bathrooms, beach, rural, washing machine
  • $2,500 - $3,700/week
  • Calendar Last Updated On: Jul 11, 2008
Classic, fully updated Vineyard home on three acres, in a quiet location, surrounded by farms and conservation land, just a few minutes to Menemsha and Lucy Vincent...
SPECIAL OFFER! Marked down from $4800 to $4000. August 24 - August 31

Stunning Views and Sunsets – Property 182266

  • Chilmark rental - cottage, 3 bedrooms, sleeps 8, 3 bathrooms, beach, waterfront, washing machine
  • $2,800 - $4,800/week
  • Calendar Last Updated On: Jun 27, 2008
Great beach house on Menemsha Pond. Expansive views of the pond, Vineyard Sound, the Elizabeth Islands. Deer, osprey, cormorants are among the wildlife crossing the...

Striking Contemporary with Views of the Sound – Property 116899

  • Chilmark rental - house, 4 bedrooms, sleeps 16, 4 bathrooms, washing machine, internet access
  • Calendar Last Updated On: Jun 16, 2008
Come enjoy the secluded beauty of this award-winning, architect-designed home in Chimark on almost four wooded acres of land.

Lovely House with Deep Water View – Property 106127

  • Chilmark rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, near the ocean, air-conditioning
  • Calendar Last Updated On: Jun 15, 2008
This is a lovely house, looking over Lucy Vincent Beach, Squibnocket and Nomans Island. The water view is wonderful from the deck as well as from the living room,...

Stone Walls, Flowery Meadows, Ocean View, renovated – Property 119314

  • Chilmark rental - house, 3 bedrooms, sleeps 5, 1 bathroom, 1 half bath, near the ocean, rural, washing machine
  • $2,000 - $2,800/week
  • Calendar Last Updated On: Jun 5, 2008
Summer cottage, cathedral ceilings, fireplace. monumental stone walls, flowery meadows, view of Lucy Vincent Beach and waters beyond, tall pines behind with a back...

Sunny, hilltop home with treetop view – Property 187239

  • Chilmark rental - house, 3 bedrooms, sleeps 6, 1 bathroom, near the ocean, resort, air-conditioning
  • $2,900 - $3,500/week
  • Calendar Last Updated On: May 22, 2008
Our home is an open design of kitchen, dining, living areas built in 1993 with all modern amenities... Light and sunny, comfortable and private.

Secluded Chilmark summer house with sweeping Atlantic views – Property 164828

  • Chilmark rental - house, 5 bedrooms, sleeps 8, 3 bathrooms, near the ocean, rural, washing machine
  • $3,500 - $4,990/week
  • Calendar Last Updated On: May 14, 2008
Come enjoy this unique summer home, perched on a secluded hilltop with stunning 180 degree views of the Atlantic Ocean. The multi level interior is airy and bright...

Spacious, Sunny, Private Chilmark Home – Property 136112

  • Chilmark rental - house, 4 bedrooms, sleeps 10, 3 bathrooms, internet access, linens provided
  • $2,000 - $5,000/week
  • Calendar Last Updated On: May 4, 2008
This spacious, comfortable, well-equipped home is located in a quiet neighborhood off North Road in Chilmark. It features 3 acres of woods and fields with...

Panoramic Ocean Views with Chilmark Charm – Property 114611

  • Chilmark rental - house, 5 bedrooms, sleeps 9, 4 bathrooms, 2 half baths, near the ocean, air-conditioning
  • Calendar Last Updated On: Jan 21, 2008
This comfortable contemporary home includes a key to a private beach and is ideal for laid-back Vineyard living, or elegant entertaining with both ocean and hillside...
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