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Chilmark Vacation Home Rentals(156)

156 Results
  • 3 BR,
  • 1 BA,
  • Sleeps 8
2 - 7 night minimum stay
(3)
$4,000 - $5,000
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
7 night minimum stay
(4)
$1,500 - $3,500
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(3)
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
2 Reviews
$1,799 - $2,695
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(5)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
$4,500 - $7,000
per week
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
(4)
$400 - $786
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
(5)
  • 6 BR,
  • 2 BA,
  • Sleeps 12
(6)
$1,575
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 8
7 night minimum stay
1 Review
$1,500
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
7 night minimum stay
(5)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
1 Review
$3,500 - $5,500
per week
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
2 Reviews
$520 - $643
per night
4 - 7 night minimum stay
  • 3 BR,
  • 4 BA,
  • Sleeps 9
4 - 7 night minimum stay
1 Review
$2,450 - $5,005
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$3,010 - $6,510
per week
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
7 night minimum stay
$1,000 - $3,000
per week
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
2 Reviews
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
$150
per night
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
  • 4 BR,
  • 2 BA,
  • Sleeps 8
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night minimum stay
$1,806 - $2,905
per week
7 night minimum stay
  • 3 BR,
  • Sleeps 6
7 night minimum stay
2 Reviews
$1,800 - $2,800
per week
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 3 HF BA,
  • Sleeps 5
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 2
7 night minimum stay
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Recent Chilmark Reviews

Great location, great owner, comfortable home

5 of 5
This house worked extremely well for our family of four. It is tucked away off of Middle Road, so has a ton of privacy, and is on a very quiet part of the Island, with access to the best beach - Lucy Vincent (a few minutes away by car). The owner was very helpful and the house was well stocked with supplies, and we grilled in the back yard and ate on the upstairs deck every night, which was great. The open layout of the very sunny upstairs (combined living room, dining area, kitchen, plus access to deck) made this a very homey spot to come back to after a day out. The bedrooms are simple and adequate. We would definitely rent this house again, it stands up extremely well against others in its price range.
  • Submitted: Oct 1, 2014
  • Stayed: Aug 2014

A place of unique tranquillity

5 of 5
This is a very special house in a magnificent setting. Even by high Vineyard standards, it has extraordinarily vast water views from the expansive deck. And at the same time its wooded setting offers complete privacy: there is no other residence in sight, only treetops. The house itself is elegant and very personal, furnished with treasures from all over the world. It is also robust and proved perfect for our large family group ranging in age from 12 to 84. We loved walking the meandering wooded trail to the Brickyard beach and were often the only people there. We will certainly return and would heartily recommend a stay here to anyone who treasures tranquillity.
  • Submitted: Sep 13, 2014
  • Stayed: Aug 2014

Perfect slice of the island!!

5 of 5
This home is perfect for a couple. My husband and I were fortunate enough to rent this home for a week. Not only was it immaculate upon arrival but it was everything we had hoped it would be. The location is perfect. The beach was amazing (we highly recommend springing for the LVB sticker if you are staying the week) and we can't say enough about the owner who was not only a wonderful man but very accommodating. We will be back, no question about it. If you want to get away from it all and truly enjoy what the Vineyard has to offer...you found the perfect rental.
  • Submitted: Sep 9, 2014
  • Stayed: Aug 2014