Holiday rentals near Oak Bluffs Harbor
We found 1,660 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 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
8% off
Price is NZ$7,960
NZ$7,960
NZ$1,137 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
8% off
Price is NZ$5,057
NZ$5,057
NZ$722 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 NZ$27,677
NZ$27,677
NZ$3,954 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 NZ$11,245
NZ$11,245
NZ$1,606 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 NZ$7,981
NZ$7,981
NZ$1,140 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 NZ$20,470
NZ$20,470
NZ$2,924 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 NZ$3,703
NZ$3,703
NZ$529 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 NZ$7,450
NZ$7,450
NZ$1,064 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 NZ$14,890
NZ$14,890
NZ$2,127 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 NZ$5,400
NZ$5,400
NZ$771 per night
includes taxes & fees
Image gallery for Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond
1010 out of 10 rating
Exceptional
(18 reviews)
Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond
Oak Bluffs, MA
12% off
Price is NZ$15,755
NZ$15,755
NZ$2,251 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 NZ$7,022
NZ$7,022
NZ$1,003 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
8% off
Price is NZ$10,534
NZ$10,534
NZ$1,505 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 NZ$10,702
NZ$10,702
NZ$1,529 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 NZ$9,259
NZ$9,259
NZ$1,323 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 NZ$5,058
NZ$5,058
NZ$723 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 NZ$20,573
NZ$20,573
NZ$2,939 per night
includes taxes & fees
Image gallery for Charming pond front New Seabury resort area
1010 out of 10 rating
Exceptional
(13 reviews)
Charming pond front New Seabury resort area
Mashpee, MA
8% off
Price is NZ$11,142
NZ$11,142
NZ$1,592 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 NZ$8,554
NZ$8,554
NZ$1,222 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
7% off
Price is NZ$11,384
NZ$11,384
NZ$1,626 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 NZ$5,618
NZ$5,618
NZ$803 per night
includes taxes & fees
Image gallery for Edgartown Escape, Spacious 4 Br, Quite Conveniently Located
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Edgartown Escape, Spacious 4 Br, Quite Conveniently Located
Edgartown, MA
7% off
Price is NZ$6,100
NZ$6,100
NZ$871 per night
includes taxes & fees
Image gallery for The perfect home for a family summer vacation! Minutes to beaches & bike path.
1010 out of 10 rating
Exceptional
(55 reviews)
The perfect home for a family summer vacation! Minutes to beaches & bike path.
East Falmouth, MA
7% off
Price is NZ$5,331
NZ$5,331
NZ$762 per night
includes taxes & fees
Image gallery for Best Kept Secret Retreat for Adults with Water & Golf Course Views!
1010 out of 10 rating
Exceptional
(37 reviews)
Best Kept Secret Retreat for Adults with Water & Golf Course Views!
Oak Bluffs, MA
7% off
Price is NZ$20,823
NZ$20,823
NZ$2,975 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)
Oak Bluffs - Quiet neighborhood
Sleeps 8 · 4 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
41 reviews(41 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
77 reviews(77 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