Oak Bluffs Vacation Rentals & Cottages - 620 Rentals Available
620 Vacation rentals

Ocean, lake, harbor and parkview Vineyard cottage
Oak Bluffs Cottage
- 6 bedrooms 6
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Nearest beach 0.2 mi
- Child friendly
- Car not necessary
Responds fast! Avg. 17 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
$328.00
from $328.00 / night

Adorable Cottage Walking Distance to Town and Beach
Oak Bluffs House
- 4 bedrooms 4
- 1 bathroom
- sleeps 7 7
- min stay varies
- Ask about children
$214.00
from $214.00 / night

WATERFRONT HOME WITH PRIVATE BEACH
Oak Bluffs House
- 7 bedrooms 7
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Ask about children
$1,000.00
from $1,000.00 / night

COZY,CUTE COTTAGE NEAR TOWN & BEACH.
Oak Bluffs House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Ask about children
- Air conditioning
$129.00
from $129.00 / night
TOTHG - Adorable Updated Vineyard Cottage, Lovely Landscaped Yard, Central A/C,
Oak Bluffs House
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Ask about children
- Air conditioning
$300.00
from $300.00 / night
BRANF - Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Sc
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 7 7
- 7 nights min
- Ask about children
- Air conditioning
$558.00
from $558.00 / night
WHARG - Beautifully Decorated, Private Tennis Court, Walk to Town Center and Ink
Oak Bluffs House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$586.00
from $586.00 / night
ALLER - Oak Bluffs 4 Bedroom Home, Walk to Town and Beach!
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$415.00
from $415.00 / night
LIJOY - Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, B
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$358.00
from $358.00 / 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
$400.00
from $400.00 / night
BURBR - Perfect Retreat for Large Families, 1.5 miles Oak Bluffs Town Center
Oak Bluffs House
- 6 bedrooms 6
- 3 bathrooms
- sleeps 13 13
- 7 nights min
- Ask about children
- Air conditioning
$643.00
from $643.00 / night
KEEFJ - Historic Waterfront Home Located just 1 Mile from Oak Bluffs Center, Pri
Oak Bluffs House
- 7 bedrooms 7
- 3 bathrooms
- sleeps 12 12
- 7 nights min
- Ask about children
- Air conditioning
$2,143.00
from $2,143.00 / night
TRAVM - Updated East Chop Area Summer Retreat, Great Proximity to Town Center an
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$400.00
from $400.00 / night
LECAY - Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bed
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
QUINTESSENTIAL VINEYARD SUMMER HOME
Oak Bluffs House
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Ask about children
$500.00
from $500.00 / night
Charming Oak Bluffs Cottage
Oak Bluffs House
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- min stay varies
- Ask about children
- Air conditioning
$357.00
from $357.00 / night
Enjoy Sea Breezes from third floor roof deck!
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- min stay varies
- Ask about children
- Air conditioning
$904.00
from $904.00 / night
SMEDM - Retreat to this Lovely Vacation Home with Main and Guest House, Central
Oak Bluffs House
- 7 bedrooms 7
- 3 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$572.00
from $572.00 / night
PETEO - Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
Oak Bluffs Cape Not too Far from Town
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- min stay varies
- Ask about children
- Air conditioning
$229.00
from $229.00 / 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
$371.00
from $371.00 / night
Lovely Oak Bluffs home one mile from town and beach
Oak Bluffs House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 9 9
- min stay varies
- Ask about children
$514.00
from $514.00 / night
THORB - Contemporary 5 Bedroom 4 Bath, Multiple Living Spaces, Walk to Oak Bluff
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$329.00
from $329.00 / night
Cute Guest House Overlooking the Lagoon
Oak Bluffs House
- 2 bedrooms 2
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Ask about children
- Air conditioning
$1,143.00
from $1,143.00 / night
OAK BLUFFS VICTORIAN ONE BLOCK FROM BEACH, TWO BLOCKS FROM TOWN!
Oak Bluffs House
- 6 bedrooms 6
- 3 bathrooms
- sleeps 12 12
- min stay varies
- Ask about children
- Air conditioning
$929.00
from $929.00 / night
Five bedroom, in-town, Oak Bluffs home with water views!
Oak Bluffs House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
$571.00
from $571.00 / night
ADELM - Waterfront Lagoon, Deck with Gorgeous Sunset Views, WiFi
Oak Bluffs House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$250.00
from $250.00 / night
Lovely three bedroom home located in the Hidden Cove area of Oak Bluffs
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
- Air conditioning
$286.00
from $286.00 / night
WOODO - Weku House, Luxury Living, Features Outstanding Entertainment Level, Gu
Oak Bluffs House
- 6 bedrooms 6
- 5 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$1,286.00
from $1,286.00 / night
PATTP - Adorable Pristine Cape, Close to Town Center and Ink Well Beach. Landsca
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$222.00
from $222.00 / night
CLASSIC, VINTAGE,GINGERBREAD
Oak Bluffs House
- 7 bedrooms 7
- 3 bathrooms
- sleeps 14 14
- min stay varies
- Ask about children
$543.00
from $543.00 / night
GUIDT - Pennacook Victorian House, Covenient In-town Location, Walk to Beach, En
Oak Bluffs House
- 5 bedrooms 5
- 1 bathroom
- sleeps 6 6
- 7 nights min
- Ask about children
$297.00
from $297.00 / night
GOYEA - Farm Neck Cottage, Short Walk to Association Waterfront on SengeKontacke
Oak Bluffs House
- 4 bedrooms 4
- 1 bathroom
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$358.00
from $358.00 / 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
$357.00
from $357.00 / night
Seaglass Cottage on East Chop
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
- Air conditioning
$414.00
from $414.00 / 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
ROCHA - Bridle Path House, Quiet Lovely Neighbohood, Porch and Deck Areas, Lar
Oak Bluffs House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$558.00
from $558.00 / night
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