Oak Bluffs Vacation Rentals & Cottages - 114 Rentals Available
114 Vacation rentals
Charming Oak Bluffs Home
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 7 7
- 7 nights min
- Ask about children
- Pet friendly
$350
from $350 / night
Four Bedroom Home, on Lagoon with Private Dock
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$930
from $930 / night
MOORR - Adorable Renovated Vacation Home, WiFi, Patio, Large Yard, Central
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$225
from $225 / night
Victorian jewel on sought after Ocean Park in Oak Bluffs
Oak Bluffs House
- 4 bedrooms 4
- 5 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$1429
from $1429 / 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
from $529 / night
HAYEL - Gingerbread Cottage, Walk to Town, Harbor Area and Inkwell Beach
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 7 7
- 7 nights min
- Ask about children
- Air conditioning
$483
from $483 / night
GIORP - Cute and Cozy Oak Bluffs Cottage, Spacious Deck, Just over a Mile to
Oak Bluffs House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 5 5
- 7 nights min
- Ask about children
- Air conditioning
$197
from $197 / night
ARMSA - Cozy Newly updated Seashore Cottage, East Chop Highlands Area
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$304
from $304 / night
CHARMING WATERFRONT HOME
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$457
from $457 / night
ROSKH - East Chop Beachfront Home, Waterviews, Hi Speed Internet, Central A/C
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$522
from $522 / night
Adorable Cottage Walking Distance to Town and Beach
Oak Bluffs House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
$214
from $214 / 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
$143
from $143 / night
ROBIH - Seaview Condo Unit, Gorgeous Waterviews, In Town Location, Modern
Oak Bluffs House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$172
from $172 / night
OCALC - Adorable Campground Cottage, Overlooks Park , Walk to Town and Ink Well
Oak Bluffs House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Ask about children
$286
from $286 / 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
from $329 / night
TOTHG - Adorable Updated Vineyard Cottage, Lovely Landscaped Yard, Central
Oak Bluffs House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 5 5
- 7 nights min
- Ask about children
- Air conditioning
$243
from $243 / night
WONDERFUL,SPACIOUS, LOVINGLY MAINTAINED HOME IN SENGEKONTACKET AREA
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$314
from $314 / night
Sweet Downtown Gingerbread Cottage (410)
Oak Bluffs House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 6 6
- 7 nights min
- Ask about children
$343
from $343 / night
HODGO - ADORABLE, RECENTLY RENOVATED COTTAGE, WALK TO TOWN, BEACH and FERRY
Oak Bluffs House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$225
from $225 / 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
$571
from $571 / 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
$357
from $357 / night
ENJOY WATERVIEWS OF SENGENKONTACKET POND FROM THE WONDERFUL DECK
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$230
from $230 / night
BRANF - Exquistie Contemporary Home in Fresh Pond Estates, Screened Porch
Oak Bluffs House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$422
from $422 / night
DOWLJ - Waterfront, Beachfront, 5 Minutes to Town and Activities
Oak Bluffs House
- 6 bedrooms 6
- 3 bathrooms
- Sleeps 12 12
- 7 nights min
- Ask about children
$786
from $786 / night
Beautiful Campground Victorian Home in Oak Bluffs
Oak Bluffs House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
- Air conditioning
$357
from $357 / night
BACOL - Charming Waterview Home, Immaculate Beachy Interior, Spacious Shady
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$429
from $429 / night
Oak Bluffs Victorian-Nantucket Sound Views from every room!
Oak Bluffs House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
$686
from $686 / night
GUIDT - Pennacook Victorian House, Covenient In-town Location, Walk to Beach
Oak Bluffs House
- 5 bedrooms 5
- 1 bathroom
- Sleeps 8 8
- 7 nights min
- Ask about children
$297
from $297 / night
VANAL - Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 7 7
- 7 nights min
- Ask about children
- Air conditioning
$533
from $533 / night
COME EXPERIENCE THE MAGIC OF THE VINEYARD
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Air conditioning
$143
from $143 / night
LEHNP - Beach Front East Chop Cottage, Spectacular Views, Perfect Getaway
Oak Bluffs House
- 1 bedroom 1
- 1 bathroom
- Sleeps 3 3
- 7 nights min
- Ask about children
$247
from $247 / night
WESTW - Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of
Oak Bluffs House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 12 12
- 7 nights min
- Ask about children
- Air conditioning
$365
from $365 / night
Enjoy the charm of a Vineyard cottage with all the amenities of today
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Air conditioning
$243
from $243 / night
LARST - Adorable Oak Bluffs Cottage just Minutes to Oak Bluffs Center and
Oak Bluffs House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$215
from $215 / 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
$172
from $172 / night
WONDERFUL VIEWS OF SENGEKONTACKET POND FROM THIS LOVELY VINEYARD HOME
Oak Bluffs House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$357
from $357 / night
SCHUS - Waterfront, Waterview
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$379
from $379 / night
PATTP - Adorable Pristine Cape, Close to Town Center and Ink Well Beach
Oak Bluffs House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$258
from $258 / night
Gracious five bedroom in-town Oak Bluffs victorian
Oak Bluffs House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 9 9
- 7 nights min
- Ask about children
- Air conditioning
$586
from $586 / 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
$258
from $258 / night
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