Oak Bluffs Vacation Rentals & Cottages - 771 Rentals Available
771 Vacation rentals
Ocean, lake, harbor and parkview Vineyard cottage
Oak Bluffs Cottage
- 6 bedrooms 6
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Child friendly
- Car not necessary
- Air conditioning
Responds fast! Avg. 57 minutes
$500.00
from $500.00 / night
KRIEH - Lagoon Waterfront Luxury Home with Pool , 500' of Private Sandy Lagoon B
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 7 7
- 10 nights min
- Swimming pool
- Ask about children
- Air conditioning
$2,143.00
from $2,143.00 / night
BRIGY - Outstanding Designer Luxury Home, 18 X 30' Pool, Expansive Bluestone P
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,143.00
from $1,143.00 / night
MARSJ - Waterview Farms Summer Home, Peaceful, Pristine Community of Homes, Wrap
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$286.00
from $286.00 / night
ROBIH - Seaview Condo Unit, Gorgeous Waterviews, In Town Location, Modern updat
Oak Bluffs House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$229.00
from $229.00 / night
GOLLB - Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi
Oak Bluffs House
- 3 bedrooms 3
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$193.00
from $193.00 / night
MURPL - Meadow View Farms House, Beautiful Tri- Level Contemporary Spacious Bri
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$401.00
from $401.00 / night
PETEV - Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association T
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$352.00
from $352.00 / night
GOLDF - Outstanding Summer Home with Pool, Screened Porch, and Patio Area, Assoc
Oak Bluffs House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$572.00
from $572.00 / night
SAMAJ - Gorgeous Ocean View Cottage Home, Ink Well Beach Across Street, Walk to
Oak Bluffs House
- 6 bedrooms 6
- 3 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
$572.00
from $572.00 / night
BACOL - Charming Waterview Home, Immaculate Beachy Interior, Spacious Shady Dec
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
MOORR - Adorable Renovated Vacation Home, WiFi, Patio, Large Yard, Central A/C,
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$201.00
from $201.00 / 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
$2,143.00
from $2,143.00 / night
CLARO - New Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 7 7
- 7 nights min
- Ask about children
- Air conditioning
$315.00
from $315.00 / 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
CENCR - Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Grea
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
WESTW - Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sen
Oak Bluffs House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 12 12
- 7 nights min
- Ask about children
- Air conditioning
$365.00
from $365.00 / 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
$558.00
from $558.00 / night
Wonderful Spacious Oak Bluffs Home with Heated Pool
Oak Bluffs House
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$714.00
from $714.00 / night
ARMSA - Cozy Newly updated Seashore Cottage, East Chop Highlands Area, Farmers
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$286.00
from $286.00 / 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
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
SCHLE - PICTURESQUE WATER VIEWS ACROSS CONSERVATION LAND TO SENGEKONTACKET, SPA
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
REIDK - Meadow View Beauty - Association Tennis, Miles of Bike Paths, 5 Min Driv
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$443.00
from $443.00 / night
Completely Renovated Cottage Close to Town
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$715.00
from $715.00 / night
GIORP - Cute and Cozy Oak Bluffs Cottage, Spacious Deck, Just over a Mile to Oa
Oak Bluffs House
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Ask about children
- Air conditioning
$193.00
from $193.00 / 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
$286.00
from $286.00 / night
SCHUS - Waterfront, Waterview
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
$429.00
from $429.00 / 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
HAYEL - Gingerbread Cottage, Walk to Town, Harbor Area and Inkwell Beach, Large
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 7 nights min
- Ask about children
- Air conditioning
$529.00
from $529.00 / night
FISHJ - Stylish Contemporary Vacation Home situated in Meadow View Farms, Open L
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$358.00
from $358.00 / 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
$329.00
from $329.00 / night
DEPUG - Lagoon Guest House, Pretty Waterview from Deck, Walk to Private Lagoon B
Oak Bluffs House
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 7 nights min
- Ask about children
$193.00
from $193.00 / night
Beautiful Oak Bluffs home on Lagoon Pond with Pool!
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
DOHEM - East Chop Seaside Cottage, Large Porch, WiFi, Spectacular Views
Oak Bluffs House
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 7 nights min
- Ask about children
$529.00
from $529.00 / night
SMYTP - Waterfront - Lagoon, Dock, Privacy and Magnificent Views, Wifi, A/C (2nd
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$272.00
from $272.00 / night
SMYTS - Waterfront, Waterview, Private Beach Lagoon, Wifi Internet
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 7 nights min
- Ask about children
- Air conditioning
$229.00
from $229.00 / night
MCBAA - Walk to Town. Hi Speed Internet.
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$229.00
from $229.00 / night
TRAVM - Updated East Chop Area Summer Retreat, Great Proximity to Town Center a
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$401.00
from $401.00 / night
BURBR - Perfect Retreat for Large Families, Newly updated, 1.5 miles to Town an
Oak Bluffs House
- 6 bedrooms 6
- 3 bathrooms
- sleeps 13 13
- 7 nights min
- Ask about children
- Air conditioning
$354.00
from $354.00 / night
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