Oak Bluffs Houses, Vacation Rentals & more


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Travelers going to Oak Bluffs are booking September dates now. Secure your vacation rental today and have the perfect trip.

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Adorable Cottage Walking Distance to Town and Beach

  • 4
  • 7
  • Min stay varies

$214

Details

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Inviting cottage, water access nearby, spacious porch for entertaining!

  • 2
  • 4
  • Min stay varies

$217

Details

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Water Front 6 Bedroom Oak Bluffs Home with Dock

  • 6
  • 10
  • 7 nights min

$1714

Details

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CHARMING WATERFRONT HOME

  • 4
  • 8
  • Min stay varies

$458

Details

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Oak Bluffs Victorian-Nantucket Sound Views from every room!

  • 5
  • 8
  • 7 nights min

$744

Details

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Guest Room in a Cozy Cottage

  • 1
  • 2
  • 3 nights min

$130

Details

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Summer Home- By the Lagoon

  • 3
  • 6
  • Min stay varies

$201

Details

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WATERFRONT HOME WITH PRIVATE BEACH

  • 7
  • 12
  • Min stay varies

$1001

Details

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Charming house with lots of entertainment and gourmet kitchen!

  • 3
  • 6
  • Min stay varies

$107

Details

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Oak Bluffs Contemporary Summer Home

  • 3
  • 6
  • 7 nights min

$243

Details

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Charming Farmhouse

  • 4
  • 8
  • 7 nights min

$401

Details

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A deck, an enclosed yard - walking distance to the beach, ferry & town!

  • 5
  • 12
  • Min stay varies

$155

Details

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Beautiful Water Front Oak Bluffs Home

  • 4
  • 8
  • Min stay varies

$929

Details

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WONDERFUL VINEYARD HOME WITH BEAUTIFUL WATERVIEWS

  • 3
  • 7
  • Min stay varies

$286

Details

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ARMSA - Cozy Newly updated Seashore Cottage, East Chop Highlands Area

  • 3
  • 6
  • 7 nights min

$305

Details

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Great Four Bedroom Home in Meadow View Farms

  • 4
  • 7
  • Min stay varies

$286

Details

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Charming 3br Getaway in Oak Bluffs

  • 3
  • 6
  • Min stay varies

$250

Details

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Seaglass Cottage on East Chop

  • 3
  • 6
  • Min stay varies

$330

Details

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Beautiful four bedroom home in-town Oak Bluffs

  • 4
  • 8
  • Min stay varies

$429

Details

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Wonderful Four Bedroom Home in Oak Bluffs

  • 4
  • 8
  • Min stay varies

$357

Details

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OAK BLUFFS VICTORIAN ONE BLOCK FROM BEACH, TWO BLOCKS FROM TOWN!

  • 6
  • 12
  • Min stay varies

$572

Details

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Charming Oak Bluffs Cottage

  • 2
  • 6
  • Min stay varies

$214

Details

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Newly Renovated 2 Bedroom Oak Bluffs House within Walking Distance to Town

  • 2
  • 5
  • Min stay varies

$286

Details

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Victorian jewel on sought after Ocean Park in Oak Bluffs

  • 4
  • 6
  • 7 nights min

$1430

Details

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Recent reviews for Oak Bluffs

"Beach cottage feel with all the comforts"

Left on 07/31/2017 for a stay in July 2017
This is a great Vineyard cottage that gives you the beach house feel with all the amenities. Rick is very easy to deal with and the process is seamless. The porch is amazing and you don't have to drive to Menemsha for the sunsets. The beds are comfortable and the renovated baths and kitchen are fantastic. Our family truly enjoyed our stay at the Blue Whale.

"very happy with our choice"

Left on 09/10/2016 for a stay in September 2016
There are 4 bathrooms in main house, and one outside shower. I have never been in a property that was so well stocked. There was a sewing kit in a night stand. There are beds everywhere. Two down in the cellar, two in the TV room, one in the kitchen. Master bedroom had a king and a single bed in room. Two beds in walk in closet. The rest of bedrooms had full to queen size beds. There were three refrigerators two in garage, and one in kitchen. Plenty of sitting for large group. There were nicely landscaped grounds all around the house. Plenty of privacy from any neighbors.

"Not a happy renter"

Left on 08/01/2017 for a stay in July 2017
The house was cute, but it was not that cleaned. The owner requested no pets, and they own a pet and their was dog hair everywhere and dust. I own dogs and if I going to rent out my property I would make sure that it was completely cleaned before i rented.

"Oak Bluffs Locale"

Left on 08/13/2017 for a stay in August 2017
Older home with antique furnishings and flea market finds offers great location and ambience for visitors to Oak Bluffs. Front porch seating points an eye to the park and ocean and gives an opportunity to speak to walkers and bikers passing by. Sometimes it's all about location and less about modern updates.
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