Holiday rentals near Oak Bluffs Harbor
We found 1,662 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:21 Nov - 28 Nov
Image gallery for Sanctuary House: An ocean-view farmhouse retreat
1010 out of 10 rating
Exceptional
(30 reviews)
Sanctuary House: An ocean-view farmhouse retreat
Vineyard Haven, MA
7% off
Price is AU$7,348
AU$7,348
AU$1,050 per night
includes taxes & fees
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
7% off
Price is AU$4,658
AU$4,658
AU$665 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 AU$24,407
AU$24,407
AU$3,487 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
8% off
Price is AU$10,317
AU$10,317
AU$1,474 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
8% off
Price is AU$12,682
AU$12,682
AU$1,812 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 AU$7,367
AU$7,367
AU$1,052 per night
includes taxes & fees
Image gallery for MOST CHIC SPOT! Your Martha's Vineyard Getaway!
1010 out of 10 rating
Exceptional
(7 reviews)
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs, MA
8% off
Price is AU$18,240
AU$18,240
AU$2,606 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
7% off
Price is AU$3,409
AU$3,409
AU$487 per night
includes taxes & fees
Image gallery for WALK to Cape Pogue Bay, Blackbird Café & enjoy our private, spacious property.
1010 out of 10 rating
Exceptional
(7 reviews)
WALK to Cape Pogue Bay, Blackbird Café & enjoy our private, spacious property.
Edgartown, MA
8% off
Price is AU$6,872
AU$6,872
AU$982 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 AU$3,923
AU$3,923
AU$560 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 AU$13,391
AU$13,391
AU$1,913 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 AU$6,594
AU$6,594
AU$942 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
(15 reviews)
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME
Mashpee, MA
8% off
Price is AU$6,417
AU$6,417
AU$917 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 AU$4,823
AU$4,823
AU$689 per night
includes taxes & fees
Image gallery for Exclusive Oyster Pond Retreat With Private Beach Access and New Gourmet Kitchen
1010 out of 10 rating
Exceptional
(43 reviews)
Exclusive Oyster Pond Retreat With Private Beach Access and New Gourmet Kitchen
Edgartown, MA
8% off
Price is AU$11,199
AU$11,199
AU$1,600 per night
includes taxes & fees
Image gallery for Contemporary and Spacious South Cape Beach Home !!!
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Contemporary and Spacious South Cape Beach Home !!!
Mashpee, MA
8% off
Price is AU$9,751
AU$9,751
AU$1,393 per night
includes taxes & fees
Image gallery for Falmouth Vacation Home at Country Club -Close to beach, ferry, golf and biking
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Falmouth Vacation Home at Country Club -Close to beach, ferry, golf and biking
East Falmouth, MA
8% off
Price is AU$9,010
AU$9,010
AU$1,287 per night
includes taxes & fees
Image gallery for Walk to Town! Beautiful, Private Edgartown Home
1010 out of 10 rating
Exceptional
(27 reviews)
Walk to Town! Beautiful, Private Edgartown Home
Edgartown, MA
7% off
Price is AU$9,696
AU$9,696
AU$1,385 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 AU$8,446
AU$8,446
AU$1,207 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 AU$18,327
AU$18,327
AU$2,618 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 AU$7,896
AU$7,896
AU$1,128 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 AU$4,521
AU$4,521
AU$646 per night
includes taxes & fees
Image gallery for Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
1010 out of 10 rating
Exceptional
(15 reviews)
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
East Falmouth, MA
8% off
Price is AU$9,845
AU$9,845
AU$1,406 per night
includes taxes & fees
Image gallery for Cozy New TimberFrame Vineyard Haven!
1010 out of 10 rating
Exceptional
(25 reviews)
Cozy New TimberFrame Vineyard Haven!
Vineyard Haven, MA
8% off
Price is AU$5,173
AU$5,173
AU$739 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
8.88.8 out of 10
Excellentexcellent
3 reviews(3 reviews)
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
Sleeps 9 · 5 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Oak Bluffs - Quiet neighborhood
Sleeps 8 · 4 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
41 reviews(41 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)
Spacious 5-bedroom house with AC and WiFi in brilliant Oak Bluffs
Sleeps 10 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Walk to Lambert's Cove Beach. Pastoral setting. Elegant farmhouse & guest house.
Sleeps 10 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
81 reviews(81 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