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Oak Bluffs Downtown Vacation Rentals Vacation Rentals(60)

60 Results
$5,000
per week
7 night minimum stay
  • 5 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 9
7 night minimum stay
(5)
$4,000
per week
7 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 15
7 night minimum stay
2 Reviews
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
$1,250 - $3,900
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(7)
  • 9 BR,
  • 7 BA,
  • 2 HF BA,
  • Sleeps 24
(3)
  • 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)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
1 Review
$700 - $1,214
per night
1 - 7 night minimum stay
  • 7 BR,
  • 6 BA,
  • Sleeps 14
1 - 7 night minimum stay
(6)
$250 - $357
per night
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
4 - 7 night minimum stay
2 Reviews
$3,000
per week
7 night minimum stay
  • 7 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 9
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 night minimum stay
1 Review
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night minimum stay
$3,500 - $6,500
per week
7 night minimum stay
  • 6 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night minimum stay
(8)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 7 night minimum stay
(8)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
(4)
  • 3 BR,
  • 1 BA,
  • Sleeps 8
2 - 7 night minimum stay
(11)
$1,495 - $2,295
per week
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 7
3 - 7 night minimum stay
(7)
  • 4 BR,
  • Sleeps 8
7 night minimum stay
(8)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
(5)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(6)
$2,800 - $3,600
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
7 night minimum stay
(14)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
1 Review
$1,650
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
7 night minimum stay
(13)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
  • 7 BR,
  • 2 BA,
  • Sleeps 15
7 night minimum stay
$1,750 - $3,000
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
2 Reviews
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Recent Oak Bluffs Reviews

Cozy and Comfortable

5 of 5
We rented the downstairs of this 2 apt. rental. It is in the heart of Oak Bluffs, 1 block away from Circuit Avenue ( the tourist block). Easy walking distance to some wonderful restaurants and the harbor and steamship ferries. Back Door Donuts less than a block down the street. The apartment is very well stocked, spices, cooking supplies, linens, beach towels, umbrellas and chairs, and a small hot tub on the side of the house you can use. Bed comfortable! Loved having a washer and dryer to use on site. Reasonably priced. Sharon is lovely and attentive to all your needs, has provided great information of things to do and places to eat. We had a lovely, relaxing 8 days in the Vineyard using this as our home base. We brought out car over on the ferry and were able to get anywhere we desired, along with renting bikes down the street made for easy access to the Island. We loved eating at Brick Cellars and Chilmarks chocolates if you have transportation is not to be missed! The Bite was delicious along with Lobster Rolls at the fish shacks. Would definitely recommend this to friends and relatives.
  • Submitted: Sep 24, 2014
  • Stayed: Sep 2014

Truly a home away from home!

5 of 5
My family has been staying at this wonderful house for (I believe) the past 5+ years! We look forward so much to going back to "our" place in Oak Bluffs, It has become so loved and familiar to us that we consider it our own! The big, comfortable, well decorated rooms, clean/updated bathrooms and kitchen, wonderful deck, roomy wrap-around deck for those (rare) times when the weather isn't great, the huge dining room table where 10+ of us can sit at once -- I could go on and on. It couldn't be more convenient to downtown Oak Bluffs, the ferry, bike paths, shopping, restaurants, the supermarket . . . all in walking distance. There are too many special memories to list - hours of fun, laughs, cooking, eating, flying kites, having wine and pie on the porch, sightseeing by bike, car, or bus, playing board games and cards in the evening. It's a couple of weeks none of us ever want to miss and getting there is like coming home. You won't be disappointed!
  • Submitted: Sep 20, 2014
  • Stayed: Sep 2014

GREAT!! GREAT !! STAYCATION !!!!

5 of 5
This was the best two week vacation on the vineyard ever!! I have stayed in many houses over many years but this home was just perfect you are close to town (Walking ) yet in a quiet community, . Donna the owner was a joy , She made sure that every thing was at your fingertips that you could possibly need on a vacation. My family also rented the front house so that we were able to have a family vacation together what more can I say . Thanks Donna See you next year Ramona B
  • Submitted: Aug 26, 2014
  • Stayed: Aug 2014