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Oak Bluffs Chalets or Cottages(65)

65 Results
$200 - $407
per night
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
4 - 7 night minimum stay
1 Review
  • 5 BR,
  • 2 BA,
  • Sleeps 13
2 - 7 night minimum stay
(15)
  • 5 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 7 night minimum stay
(5)
$185 - $300
per night
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 - 7 night minimum stay
(5)
  • 2 BR,
  • Sleeps 6
2 - 4 night minimum stay
1 Review
$1,500 - $2,600
per week
7 night minimum stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
7 night minimum stay
  • 5 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
2 Reviews
$829 - $929
per night
6 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 6
6 - 7 night minimum stay
(3)
  • 6 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(7)
$1,500 - $2,500
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
2 Reviews
  • 3 BR,
  • 1 BA,
  • Sleeps 7
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 9
$40 - $340
per night
2 - 30 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 30 night minimum stay
$1,500 - $2,800
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(4)
$214 - $486
per night
3 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 9
3 - 7 night minimum stay
(5)
$247 - $347
per night
2 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
(9)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(5)
$85 - $179
per night
2 - 7 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 4
2 - 7 night minimum stay
(8)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(13)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
7 night minimum stay
(6)
$271 - $329
per night
4 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
4 - 7 night minimum stay
1 Review
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
2 Reviews
$271 - $350
per night
2 - 7 night minimum stay
  • 3 BR,
  • Sleeps 6
2 - 7 night minimum stay
(10)
  • 4 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 10
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
(9)
$1,800 - $3,200
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 night minimum stay
$3,500 - $7,500
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
7 night minimum stay
1 Review
  • 3 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(4)
$325 - $345
per night
3 night minimum stay
  • 5 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
3 night minimum stay
1 Review
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Recent Oak Bluffs Reviews

You will fall in love...

5 of 5
The charm of a vacation in the vineyard lies in the home you stay in. And this home has plenty of charm. From its vibrant exterior to its pristinely kept interior, I fell in love with this home. It was a pleasure to meet the owner Guy, who was so warm and inviting. I stayed here with a group of friends, and it was amazing to wake up each morning, sit in the large wicker chairs on the front porch, have a coffee or mimosa and just chat the morning away while music filled the house (every room has speakers!). This home had all the comforts of home that you could think of. It felt like home so much we wanted to spend most of our time there. But since the beach is literally a 2 minute walk we couldn't resist dividing our time. My friends and I decided before the vacation was over that going forward this would always be the home we stay in during our annual visit. It was simply that great!
  • Submitted: Oct 11, 2014
  • Stayed: Jun 2014

Best of both worlds!

5 of 5
One of the best things about this house is that it makes you feel that you are far away from the hustle and bustle of OB, but in reality you are a few blocks away. You can walk downtown and down the street to the beach. The house is relaxing and quaint. Perfect getaway...
  • Submitted: Oct 10, 2014
  • Stayed: Aug 2014

Meticulous Property & Considerate Owners

5 of 5
The house is maintained and decorated beautifully. We arrived at the house and found it meticulously cleaned. The owners are responsive and exceeded our expectations. This is a fantastic way to experience the Vineyard. This was a fantastic value for the money.
  • Submitted: Sep 25, 2014
  • Stayed: Jul 2014