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Vacation Rentals in Chilmark

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Spacious, Sunny, Private Chilmark Home – Property 136112

  • Chilmark rental - house, 4 bedrooms, sleeps 12, 3 bathrooms, near the ocean, rural, jacuzzi
  • $2,500 - $4,500/week
  • Calendar Last Updated On: May 21, 2012
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...

SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING – Property 7104189

  • Chilmark rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, air-conditioning, satellite or cable
  • $1,050 - $3,000/week
  • Calendar Last Updated On: May 21, 2012
This spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. The master bedroom and bath are downstairs;...

BLACK POINT BEACH KEY! 5-acre privacy, located in Quansoo – Property 120243

  • Chilmark rental - house, 4 bedrooms, sleeps 8, beach, rural, garden
  • $2,500 - $4,000/week
  • Calendar Last Updated On: May 19, 2012
This contemporary architectural gem is shaped as a partial arc, allowing maximum privacy as there are 2 BRs and a full bath on opposite ends of the house .

FERRY TIX! Waterview, Tri-Level, 5 minutes to LV Beach + Squibby, Wifi – Property 121220

  • Chilmark rental - house, 4 bedrooms, sleeps 9, 3 bathrooms, near the ocean, rural, internet access
  • $2,250 - $4,250/week
  • Calendar Last Updated On: May 19, 2012
This renovated home offers a panoramic water view and a very large private yard. There are 3 levels; the upper level consisting of the master bedroom with a full...

FERRY TIX! Waterview, A/C, wifi, totally private 3-acre setting w/ a large yard – Property 133117

  • Chilmark rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, near the ocean, rural, garden
  • $2,000 - $3,700/week
  • Calendar Last Updated On: May 19, 2012
With a distant sweeping waterview, full privacy, and a total renovation, this property offers accommodations well above the norm.

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, pets considered
  • $1,600 - $2,550/week
  • Calendar Last Updated On: May 19, 2012
This sunny Chilmark cottage offers total privacy on your own 5 acres. Located off a small private road, we are minutes to the Chilmark Store, the library, and the...

sweeping sunset waterviews, 4-5 BR, central A/C, beach, tennis – Property 291917

  • Chilmark rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, beach, near the ocean, tennis court
  • $2,250 - $4,000/week
  • Calendar Last Updated On: May 19, 2012
This comfortable and inviting 5-acre property w/ a 1-mile assoc. beach and tennis courts has sweeping waterviews and sunsets.

PRICE REDUCED! Spacious Family Home, Ocean Views, Key to Quansoo Beach – Property 243860

  • Chilmark rental - house, 5 bedrooms, sleeps 14, 3 bathrooms, near the ocean, rural, garden
  • Calendar Last Updated On: May 19, 2012
Ours is an open, sunny house with ocean views perfect for families (single or multi-generational) and good friends. The large living room with fireplace, two seating...

Book Now 2012 Early Rates: 5 br; ocean views – Property 114611

  • Chilmark rental - house, 5 bedrooms, sleeps 9, 3 bathrooms, 1 half bath, near the ocean, rural, jacuzzi
  • Calendar Last Updated On: May 19, 2012
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...

Celebrity Owned Hilltop Waterview with Hot Tub – Property 106017

  • Chilmark rental - house, 3 bedrooms, sleeps 8, 4 bathrooms, near the ocean, rural, tennis court
  • $3,200 - $4,200/week
  • Calendar Last Updated On: May 18, 2012
Unique, 12 acre hilltop home with privacy, water view, pines, oaks, and southfacing stone terrace. The terrace has wrought iron dinning table for 8 and single and...

Chilmark/Roof Deck Sunsets Over Menemsha;Beautiful Landscaping. Can fit 2 groups – Property 231734

  • Chilmark rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, near the ocean, rural, jacuzzi
  • $3,750/week
  • Calendar Last Updated On: May 18, 2012
Charming 3-bedroom house centrally located in Chilmark. Architect-designed and Craftsman-built. Split level contemporary home contains 3 full bathrooms, a spa (hot...

French Country Farmhouse, Close to Beaches, Brand new Hot Tub AND 2pers jacuzzi – Property 994085

  • Chilmark rental - farmhouse, 3 bedrooms, sleeps 7, 2 bathrooms, near the ocean, rural, jacuzzi
  • $2,600 - $3,800/week
  • Calendar Last Updated On: May 18, 2012
Newly Listed -3 bedm 2 bath home, close to Lucy Vincent Beach ( has both nude and regular sections), and Squibnocket beach. This home is 1/2 mile past Chilmark...

Blueberry Ridge: Sweeping Views With Pool – Property 7149231

  • Chilmark rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, internet access, satellite or cable
  • $8,000/week
  • Calendar Last Updated On: May 18, 2012
Set high on Blueberry Ridge, this Chilmark retreat perfectly blends casual elegance, with sweeping ocean views and a large pool.

Chilmark Pond House With Water Views – Property 7139194

  • Chilmark rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, air-conditioning, internet access
  • $10,000 - $30,000/week
  • Calendar Last Updated On: May 18, 2012
Quietly tucked away above Chilmark Pond, this newly constructed deluxe home enjoys sweeping water views of the Pond and Atlantic Ocean, and ;features luxurious...

Blueberry Ridge: Sweeping Views With Pool – Property 7139129

  • Chilmark rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, internet access, satellite or cable
  • $8,000/week
  • Calendar Last Updated On: May 18, 2012
Set high on Blueberry Ridge, this Chilmark retreat perfectly blends casual elegance, with sweeping ocean views and a large pool.

Privacy, Serenity, Elegance, Beautiful Sunrise Views, Chilmark – Property 238938

  • Chilmark rental - house, 2 bedrooms, sleeps 4, 1 bathroom, near the ocean, rural, garden
  • $1,750 - $2,600/week
  • Calendar Last Updated On: May 18, 2012
This is an elegant 2 bedroom plus loft. It has an open dining/kitchen/living area, one bathroom, outdoor shower, and very private.

Chilmark Spectacular Views, Beach – Property 7008388

  • Chilmark rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, beach, near the ocean
  • $2,500 - $4,800/week
  • Calendar Last Updated On: May 17, 2012
This special summer retreat affords unforgettable views, a quiet and private setting, an awesome deck to sit, watch, dream, relax, entertain guests and get away...

Chimark close to Lucy Vincent Beach- CH202 – Property 7008384

  • Chilmark rental - house, 3 bedrooms, sleeps 5, 1 bathroom, 1 half bath, beach, satellite or cable
  • Calendar Last Updated On: May 17, 2012
CH202 Step back in time to a simpler and more peaceful era. This charming cottage offers three bedroom, one and one half baths.

Title – Property 7151544

  • Chilmark rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, jacuzzi, satellite or cable
  • $4,800 - $9,500/week
  • Calendar Last Updated On: May 16, 2012
Beautifully restored, maintained, and furnished, this 1740 Island farmhouse is situated on 80 private acres of glorious Chilmark hills overlooking Menemsha Pond and...

CHILMARK. Big Comfy House & Deck. 6BR, 2 BA, sleeps 12. WiFi. FERRY TIX! – Property 362288

  • Chilmark rental - house, 6 bedrooms, sleeps 12, 2 bathrooms, near the ocean, rural, garden
  • $3,250 - $3,500/week
  • Calendar Last Updated On: May 14, 2012
Big, comfy, well-equipped Chilmark house. WI-FI. Access to LUCY VINCENT and SQUIBNOCKET beaches. Has 6 full bedrooms (one downstairs for easy access), 2 full baths...
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