Oak Bluffs Cottage Rentals

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Best Oak Bluffs cottage rentals

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$99 - $748$748 - $1,397$1,397 - $2,046$2,046 - $2,694$2,694+ per night

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Most recommended cottage rentals in Oak Bluffs

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Edgartown Designer Cottage between Town & Beach. - Edgartown - Beach
Edgartown Designer Cottage between Town & Beach.
Edgartown, MA
10Wonderful(20)
Cottage
$504+
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This Romantic Cottage is Simply a Cut Above - - Edgartown - Living room
This Romantic Cottage is Simply a Cut Above -
Edgartown, MA
10Wonderful(19)
Cottage
$399+
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Martha's Vineyard 1br, Pets Ok, 10 Min Walk To Beach Or Edgartowns Shops! - Edgartown - Living room
Martha's Vineyard 1br, Pets Ok, 10 Min Walk To Beach Or Edgartowns Shops!
Edgartown, MA
9.6Wonderful(21)
Cottage
$575+
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Chappy cottage with private beach - Edgartown - Kitchen
Chappy cottage with private beach
Edgartown, MA
10Wonderful(17)
Cottage
$989+
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A Charming Vineyard Cottage Just Off the Pond - Edgartown - Living room
A Charming Vineyard Cottage Just Off the Pond
Edgartown, MA
9.8Wonderful(10)
Cottage
$798+
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Chappaquiddick, Cozy 2 Bedroom, October Dates Available! - Edgartown - Building
Chappaquiddick, Cozy 2 Bedroom, October Dates Available!
Edgartown, MA
10Wonderful(15)
Cottage
$334+
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Marthas Vineyard Home Walk To Oak Bluffs - Oak Bluffs - Balcony
Marthas Vineyard Home Walk To Oak Bluffs
Oak Bluffs, MA
10Wonderful(2)
Cottage
$462+
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Renovated Cottage with nice yard and homey interior - Edgartown - Living room
Renovated Cottage with nice yard and homey interior
Edgartown, MA
8.7Very good(13)
Cottage
$339+
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Garden Cottage--Bike to Town and Beach. Prime Katama location. Dog Friendly. - Edgartown - Patio
Garden Cottage--Bike to Town and Beach. Prime Katama location. Dog Friendly.
Edgartown, MA
9.7Wonderful(29)
Cottage
$308+
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Chappy Summer Cabin! - Edgartown - Patio
Chappy Summer Cabin!
Edgartown, MA
8.6Very good(18)
Cottage
$372+
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Perfect Adorable Cottage Retreat Among Award-Winning Gardens - Edgartown - Living room
Perfect Adorable Cottage Retreat Among Award-Winning Gardens
Edgartown, MA
9.5Wonderful(4)
Cottage
$494+
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Chappy Relaxation and Fun! - Edgartown - Living room
Chappy Relaxation and Fun!
Edgartown, MA
9.7Wonderful(7)
Cottage
$464+
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Charming and cozy Chappy cottage -- best of indoor and outdoor beach living! - Edgartown - Dining room
Charming and cozy Chappy cottage -- best of indoor and outdoor beach living!
Edgartown, MA
10Wonderful(14)
Cottage
$506+
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Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path. - Oak Bluffs - Dining room
Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path.
Oak Bluffs, MA
9.9Wonderful(55)
Cottage
$479+
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The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs - Oak Bluffs - Living room
The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs
Oak Bluffs, MA
9.5Wonderful(18)
Cottage
$846+
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Oak Bluffs Cottage - A Short Walk to the Beach! - Oak Bluffs - Living room
Oak Bluffs Cottage - A Short Walk to the Beach!
Oak Bluffs, MA
8.6Very good(9)
Cottage
$749+
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Useful Info

Good to know

Low season

High season

Average price (weeknight)

September
August
$442
Cheapest month to stay with an average 44% drop in price.
Most expensive month to stay with an average 88% rise in price.
Average Sun - Thu price over the last 2 weeks.

KAYAK's top tips for finding Oak Bluffs vacation rental deals

  • For the cheapest cottage rental in Oak Bluffs, try to visit during the low season and outside of main travel peaks. The cheapest rates can be found in September and August.

Where to stay in Oak Bluffs?

Our map will help you find the perfect place to stay in Oak Bluffs by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Oak Bluffs