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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)
  • 5 BR,
  • 5 BA,
  • Sleeps 10
7 night minimum stay
$5,000 - $7,500
per week
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
$2,700 - $4,300
per week
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
$4,000 - $6,000
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
$2,500 - $2,700
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
$6,500
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
$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
$3,000 - $7,100
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
$4,000 - $5,500
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$2,000 - $3,175
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$3,200 - $3,800
per week
7 night minimum stay
  • 3 BR,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
  • 6 BR,
  • 2 BA,
  • Sleeps 14
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
5 - 7 night minimum stay
$1,800 - $2,800
per week
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 3 HF BA,
  • Sleeps 5
7 night minimum stay
$10,500
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
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)
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Recent Chilmark Reviews

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

Great big wonderful stay!

5 of 5
We have just had our third wonderful summer stay at Tavanage. It continues to be a perfectly magical house for us. We cook cook cook in the spacious kitchen, lounge on the ever-so-peaceful back porch, and sleep cozily in all six bedrooms - we are a big brood and it's so great to have all that room to spread out. Our stay at Tavanage always feels like coming home, even the first year. It has the history and heritage of the island, as well as the modern amenities we can't seem to do without. Grilling out back is easy and relaxing, as is company for cocktails on the porch. And, as in past years, we have found that the location turns out to be ideal. Peaceful on Middle Road, and a short ride to either Alley's, the beaches, the docks at Menemsha. Everything within reach. We love our "home" at Tavanage and hope to return for many years to come!
  • Submitted: Aug 13, 2014
  • Stayed: Aug 2014

Amazing stay! Second year in a row!

5 of 5
We love this cottage. Our family of four has come here for the past two years to celebrate the 4th of July. If you love the quiet solitude of Chilmark with easy access to both a pond and gated beach, you will love this rental. We may look at renting the Tower House with is the adjacent larger home. Highly recommend this property!
  • Submitted: Jul 8, 2014
  • Stayed: Jun 2014