Oak Bluffs 4+ bedroom Vacation Rentals, Cottages & More - 178 Rentals Available.
178 Vacation rentals
Filters applied: 4+ Bedrooms

Ocean, lake, harbor & parkview Vineyard cottage w/AC
Oak Bluffs Cottage
- 6 bedrooms 6
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Child friendly
Responds fast! Avg. 20 minutes
$573.00
from $573.00 / night

Waterfront-Martha's Vineyard
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Child friendly
- Private garden
$401.00
from $401.00 / night

Luxury Oak Bluffs Home with 18 X 30' Pool
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,143.00
from $1,143.00 / night

Wonderful Contempory Home in Meadow View Farms
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$571.00
from $571.00 / night

Cape Style Home near Lagoon Pond- short walk to Lagoon Beach
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
$401.00
from $401.00 / night
OAK BLUFFS VICTORIAN ONE BLOCK FROM BEACH, TWO BLOCKS FROM TOWN!
Oak Bluffs House
- 6 bedrooms 6
- 3 bathrooms
- sleeps 11 11
- min stay varies
- Ask about children
- Air conditioning
$600.00
from $600.00 / night
CLASSIC, VINTAGE,GINGERBREAD
Oak Bluffs House
- 7 bedrooms 7
- 3 bathrooms
- sleeps 14 14
- min stay varies
- Ask about children
$929.00
from $929.00 / night
Beautiful Oak Bluffs Home with Wonderful Waterviews
Oak Bluffs House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
- Air conditioning
$1,438.00
from $1,438.00 / night
Gracious five bedroom in-town Oak Bluffs victorian
Oak Bluffs House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 9 9
- min stay varies
- Ask about children
- Air conditioning
$500.00
from $500.00 / night
Beautiful Main & Guest house short walk to Lagoon Pond
Oak Bluffs House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
Beautiful Four Bedroom Home Walking Distance to Downtown Oak Bluffs
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 9 9
- min stay varies
- Ask about children
- Air conditioning
$550.00
from $550.00 / night
Ocean Park Victorian Carousel House
Oak Bluffs House
- 6 bedrooms 6
- 3 bathrooms
- sleeps 12 12
- min stay varies
- Ask about children
- Air conditioning
$1,375.00
from $1,375.00 / night
ENJOY WATERVIEWS OF SENGENKONTACKET POND FROM THE WONDERFUL DECK
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$257.00
from $257.00 / night
Charming East Chop Home
Oak Bluffs House
- 7 bedrooms 7
- 3 bathrooms
- sleeps 12 12
- min stay varies
- Ask about children
$357.00
from $357.00 / night
Completely Renovated Cottage Close to Town
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$643.00
from $643.00 / night
Four bedroom Oak Bluffs Home
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
$414.00
from $414.00 / night
Charming Oak Bluffs Cottage within Walking Distance to Town
Oak Bluffs House
- 6 bedrooms 6
- 3 bathrooms
- sleeps 12 12
- min stay varies
- Ask about children
- Air conditioning
$714.00
from $714.00 / night
Beautiful Four Bedroom Home with Central Air Conditioning
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$489.00
from $489.00 / night
Beautiful Oak Bluffs home on Lagoon Pond with Pool!
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
Beautiful four bedroom home in-town Oak Bluffs
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
Victorian jewel on sought after Ocean Park in Oak Bluffs
Oak Bluffs House
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
- Air conditioning
$714.00
from $714.00 / night
Great Four Bedroom Home in Meadow View Farms
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- min stay varies
- Ask about children
$429.00
from $429.00 / night
CLASSIC AND CHARMING COTTAGE WALKING DISTANCE TO THE BEACH AND TOWN
Oak Bluffs House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
$201.00
from $201.00 / night
Restored Ginger Bread Home Steps from the Inkwell Beach
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
$1,714.00
from $1,714.00 / night
LUXURY WATERFRONT HOME- BEACH,DEEPWATER DOCK & MOORING
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$1,286.00
from $1,286.00 / night
WONDERFUL VIEWS OF SENGEKONTACKET POND FROM THIS LOVELY VINEYARD HOME
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
Four bedroom steps from Ink Well Beach!
Oak Bluffs House
- 4 bedrooms 4
- 1 bathroom
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
Walk to Lagoon from this Cute Cottage
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$422.00
from $422.00 / night
CHARMING WATERFRONT HOME
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
$457.00
from $457.00 / night
Wonderful Four Bedroom Home in Oak Bluffs
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
Renovated Oak Bluffs cottage steps from Ink Well Beach
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
- Air conditioning
$714.00
from $714.00 / night
Lovely Four Bedroom East Chop Home with Waterviews
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$793.00
from $793.00 / night
Classic East Chop Cottage
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
Oceanfront Home Walk to Ferry and Town
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 9 9
- min stay varies
- Ask about children
- Air conditioning
$1,071.00
from $1,071.00 / night
Beautiful Colonial in Oak Bluffs with Air Conditioning
Oak Bluffs House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 13 13
- min stay varies
- Ask about children
- Air conditioning
$857.00
from $857.00 / night
Cozy Oak Bluffs home close to beach & town.
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$801.00
from $801.00 / night
NEWLY RENOVATED, ARCHITECTURALLY SIGNIFICANT BEACH COTTAGE
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- min stay varies
- Ask about children
- Air conditioning
$372.00
from $372.00 / night
Beautiful Views Overlooking Sunset Lake to the Harbor
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$1,143.00
from $1,143.00 / night
New Four Bedroom in-town Oak Bluffs Home
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$857.00
from $857.00 / night
Waterfront Four Bedroom Sengenkontacket Pond Home
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$500.00
from $500.00 / night
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