Holiday rentals near Oak Bluffs Harbor
We found 1,658 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals close to Oak Bluffs Harbor that can be your home away from home. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you expect for your stay, which might include a garden and Wi-Fi. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Oak Bluffs Harbor
Showing deals for:14 Nov - 21 Nov
Image gallery for Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Relaxing Island Retreat, Cozy Cottage, Lamberts Cove Beach Access!
Vineyard Haven, MA
8% off
Price is S$3,846
S$3,846
S$549 per night
includes taxes & fees
Image gallery for Sanctuary House: An ocean-view farmhouse retreat
1010 out of 10 rating
Exceptional
(29 reviews)
Sanctuary House: An ocean-view farmhouse retreat
Vineyard Haven, MA
8% off
Price is S$6,096
S$6,096
S$871 per night
includes taxes & fees
Image gallery for PRIVACY & RELAXATION ON MARTHA'S VINEYARD
1010 out of 10 rating
Exceptional
(7 reviews)
PRIVACY & RELAXATION ON MARTHA'S VINEYARD
Vineyard Haven, MA
8% off
Price is S$21,890
S$21,890
S$3,127 per night
includes taxes & fees
Image gallery for Gorgeous Spacious Victorian Cape Code Beach View Retreat
1010 out of 10 rating
Exceptional
(11 reviews)
Gorgeous Spacious Victorian Cape Code Beach View Retreat
Falmouth, MA
14% off
Price is S$10,619
S$10,619
S$1,517 per night
includes taxes & fees
Image gallery for Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs
1010 out of 10 rating
Exceptional
(6 reviews)
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs
Oak Bluffs, MA
14% off
Price is S$10,651
S$10,651
S$1,522 per night
includes taxes & fees
Image gallery for Relax & Renew at this Luxury Villa with Heated Pool & Hot Tub, Tennis, Firepit!
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Relax & Renew at this Luxury Villa with Heated Pool & Hot Tub, Tennis, Firepit!
Oak Bluffs, MA
7% off
Price is S$11,056
S$11,056
S$1,579 per night
includes taxes & fees
Image gallery for Family cottage in Oak Bluffs. Close to town
8.08.0 out of 10 rating
Very good
(7 reviews)
Family cottage in Oak Bluffs. Close to town
Oak Bluffs, MA
7% off
Price is S$3,241
S$3,241
S$463 per night
includes taxes & fees
Image gallery for Edgartown Long Point Escape, Very Spacious Quite Private Location, Central A/C
1010 out of 10 rating
Exceptional
(39 reviews)
Edgartown Long Point Escape, Very Spacious Quite Private Location, Central A/C
Edgartown, MA
7% off
Price is S$6,112
S$6,112
S$873 per night
includes taxes & fees
Image gallery for Guest House In Edgartown
1010 out of 10 rating
Exceptional
(5 reviews)
Guest House In Edgartown
Edgartown, MA
8% off
Price is S$3,737
S$3,737
S$534 per night
includes taxes & fees
Image gallery for Katama Cape 5 minutes to South Beach
1010 out of 10 rating
Exceptional
(5 reviews)
Katama Cape 5 minutes to South Beach
Edgartown, MA
8% off
Price is S$7,424
S$7,424
S$1,061 per night
includes taxes & fees
Image gallery for Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
9.29.2 out of 10 rating
Wonderful
(30 reviews)
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
East Falmouth, MA
8% off
Price is S$4,063
S$4,063
S$580 per night
includes taxes & fees
Image gallery for STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME
1010 out of 10 rating
Exceptional
(14 reviews)
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME
Mashpee, MA
8% off
Price is S$5,380
S$5,380
S$769 per night
includes taxes & fees
Image gallery for A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!
1010 out of 10 rating
Exceptional
(23 reviews)
A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!
Vineyard Haven, MA
8% off
Price is S$5,447
S$5,447
S$778 per night
includes taxes & fees
Image gallery for Modern Cape Cod home in vibrant beach community - steps to beach; pool access!!
1010 out of 10 rating
Exceptional
(19 reviews)
Modern Cape Cod home in vibrant beach community - steps to beach; pool access!!
East Falmouth, MA
15% off
Price is S$4,333
S$4,333
S$619 per night
includes taxes & fees
Image gallery for Beautiful Contemporary Home, Edgartown Morning Glory Farm
1010 out of 10 rating
Exceptional
(5 reviews)
Beautiful Contemporary Home, Edgartown Morning Glory Farm
Edgartown, MA
7% off
Price is S$11,707
S$11,707
S$1,672 per night
includes taxes & fees
Image gallery for Chappaquiddick Getaway with stunning Ocean Views, walk to the beach
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Chappaquiddick Getaway with stunning Ocean Views, walk to the beach
Edgartown, MA
7% off
Price is S$8,879
S$8,879
S$1,268 per night
includes taxes & fees
Image gallery for Quiet Edgartown vacation home - 10 minutes from door to beach chair!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Quiet Edgartown vacation home - 10 minutes from door to beach chair!
Edgartown, MA
8% off
Price is S$4,358
S$4,358
S$623 per night
includes taxes & fees
Image gallery for Contemporary and Spacious South Cape Beach Home !!!
9.49.4 out of 10 rating
Exceptional
(39 reviews)
Contemporary and Spacious South Cape Beach Home !!!
Mashpee, MA
7% off
Price is S$8,443
S$8,443
S$1,206 per night
includes taxes & fees
Image gallery for Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
1010 out of 10 rating
Exceptional
(32 reviews)
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
Edgartown, MA
8% off
Price is S$6,553
S$6,553
S$936 per night
includes taxes & fees
Image gallery for Walk to Town! Beautiful, Private Edgartown Home
1010 out of 10 rating
Exceptional
(26 reviews)
Walk to Town! Beautiful, Private Edgartown Home
Edgartown, MA
7% off
Price is S$8,310
S$8,310
S$1,187 per night
includes taxes & fees
Image gallery for Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
8.08.0 out of 10 rating
Very good
(11 reviews)
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
East Falmouth, MA
8% off
Price is S$3,806
S$3,806
S$544 per night
includes taxes & fees
Image gallery for Spectacular Classic Waterfront Cottage
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Spectacular Classic Waterfront Cottage
Oak Bluffs, MA
8% off
Price is S$16,233
S$16,233
S$2,319 per night
includes taxes & fees
Image gallery for Beautiful home with pool in great location- close to everything!
1010 out of 10 rating
Exceptional
(20 reviews)
Beautiful home with pool in great location- close to everything!
Oak Bluffs, MA
8% off
Price is S$7,008
S$7,008
S$1,001 per night
includes taxes & fees
Image gallery for Cape Cod (New Seabury) Family Compound private pool near beach/dining/shopping
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Cape Cod (New Seabury) Family Compound private pool near beach/dining/shopping
Mashpee, MA
11% off
Price is S$10,127
S$10,127
S$1,447 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Oak Bluffs Harbor
Renovated Vineyard Retreat
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Oak Bluffs - Quiet neighborhood
Sleeps 8 · 4 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
39 reviews(39 reviews)
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven
Sleeps 6 · 3 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Classic Vineyard Ocean, Harbor, Lake & Parkview Cottage w/AC
Sleeps 10 · 7 bedrooms · 3 bathrooms
8.08.0 out of 10
Very goodvery good
1 review(1 review)
WATERFRONT Downtown Cottage w/ Beach
Sleeps 2 · 1 bedroom · 1+ bathroom
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value