Holiday rentals near Oak Bluffs Harbor
We found 1,661 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:26 Sept - 3 Oct
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
10% off
Price is AU$15,577
AU$15,577
AU$2,225 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
(6 reviews)
Family cottage in Oak Bluffs. Close to town
Oak Bluffs, MA
7% off
Price is AU$4,325
AU$4,325
AU$618 per night
includes taxes & fees
Image gallery for Maushop Village Getaway with Ocean Views, Steps to Private Beach
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Mashpee, MA
8% off
Price is AU$4,278
AU$4,278
AU$611 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
8% off
Price is AU$10,523
AU$10,523
AU$1,503 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
(9 reviews)
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME
Mashpee, MA
8% off
Price is AU$5,469
AU$5,469
AU$781 per night
includes taxes & fees
Image gallery for Vineyard Haven, Close to town and Lake Tashmoo
1010 out of 10 rating
Exceptional
(36 reviews)
Vineyard Haven, Close to town and Lake Tashmoo
Vineyard Haven, MA
8% off
Price is AU$5,447
AU$5,447
AU$778 per night
includes taxes & fees
Image gallery for COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.
9.89.8 out of 10 rating
Exceptional
(7 reviews)
COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.
Oak Bluffs, MA
8% off
Price is AU$9,040
AU$9,040
AU$1,291 per night
includes taxes & fees
Image gallery for Contemporary and Spacious South Cape Beach Home !!!
9.49.4 out of 10 rating
Exceptional
(34 reviews)
Contemporary and Spacious South Cape Beach Home !!!
Mashpee, MA
8% off
Price is AU$10,292
AU$10,292
AU$1,470 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$8,892
AU$8,892
AU$1,270 per night
includes taxes & fees
Image gallery for Secluded, Private Vacation Beach Home on Chappaquiddick Island, Walk To Beach.
1010 out of 10 rating
Exceptional
(11 reviews)
Secluded, Private Vacation Beach Home on Chappaquiddick Island, Walk To Beach.
Edgartown, MA
8% off
Price is AU$33,261
AU$33,261
AU$4,752 per night
includes taxes & fees
Image gallery for Studio Apartment at The Shire - Cape Cod
1010 out of 10 rating
Exceptional
(13 reviews)
Studio Apartment at The Shire - Cape Cod
East Falmouth, MA
8% off
Price is AU$2,880
AU$2,880
AU$411 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
(12 reviews)
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
East Falmouth, MA
8% off
Price is AU$9,874
AU$9,874
AU$1,411 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
(28 reviews)
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
Edgartown, MA
8% off
Price is AU$8,489
AU$8,489
AU$1,213 per night
includes taxes & fees
Image gallery for Walk to Town! Beautiful, Private Edgartown Home
1010 out of 10 rating
Exceptional
(24 reviews)
Walk to Town! Beautiful, Private Edgartown Home
Edgartown, MA
8% off
Price is AU$10,035
AU$10,035
AU$1,434 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$18,050
AU$18,050
AU$2,579 per night
includes taxes & fees
Image gallery for Modern & Tranquil Cape home close to town and beaches!
1010 out of 10 rating
Exceptional
(8 reviews)
Modern & Tranquil Cape home close to town and beaches!
East Falmouth, MA
7% off
Price is AU$5,350
AU$5,350
AU$764 per night
includes taxes & fees
Image gallery for Beautiful home with pool in great location- close to everything!
1010 out of 10 rating
Exceptional
(18 reviews)
Beautiful home with pool in great location- close to everything!
Oak Bluffs, MA
8% off
Price is AU$8,442
AU$8,442
AU$1,206 per night
includes taxes & fees
Image gallery for Charming pond front New Seabury resort area
1010 out of 10 rating
Exceptional
(11 reviews)
Charming pond front New Seabury resort area
Mashpee, MA
7% off
Price is AU$6,863
AU$6,863
AU$980 per night
includes taxes & fees
Image gallery for Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
8.68.6 out of 10 rating
Excellent
(9 reviews)
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
East Falmouth, MA
8% off
Price is AU$5,865
AU$5,865
AU$838 per night
includes taxes & fees
Image gallery for Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven
9.89.8 out of 10 rating
Exceptional
(74 reviews)
Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven
Oak Bluffs, MA
8% off
Price is AU$4,663
AU$4,663
AU$666 per night
includes taxes & fees
Image gallery for Beautiful downtown Oak Bluffs!
1010 out of 10 rating
Exceptional
(10 reviews)
Beautiful downtown Oak Bluffs!
Oak Bluffs, MA
8% off
Price is AU$8,944
AU$8,944
AU$1,278 per night
includes taxes & fees
Image gallery for Family-friendly 4 Bedroom House on Chappy - Book Now for Summer 2024
1010 out of 10 rating
Exceptional
(18 reviews)
Family-friendly 4 Bedroom House on Chappy - Book Now for Summer 2024
Edgartown, MA
8% off
Price is AU$4,827
AU$4,827
AU$690 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
12% off
Price is AU$11,676
AU$11,676
AU$1,668 per night
includes taxes & fees
Image gallery for Private home, spacious yard with easy access to everything & along the bike path
1010 out of 10 rating
Exceptional
(13 reviews)
Private home, spacious yard with easy access to everything & along the bike path
Edgartown, MA
8% off
Price is AU$14,938
AU$14,938
AU$2,134 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
1 review(1 review)
Oak Bluffs - Quiet neighborhood
Sleeps 8 · 4 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
36 reviews(36 reviews)
EXQUISITE MARTHA'S VINEYARD HOME, HEATED POOL, 10 MIN WALK TO OAK BLUFFS FERRY
Sleeps 8 · 4 bedrooms · 4+ bathrooms
Beachside Village Resort
Sleeps 4 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
93 reviews(93 reviews)
Discover the magic of Martha’s Vineyard! NEW ! Build in 2020 !
Sleeps 2 · 1 bathroom
1010 out of 10
Exceptionalexceptional
46 reviews(46 reviews)
Private Family Home, Heated Pool, Hottub, 5 BR.4.5 bath, WiFi, AC. NO PETS.
Sleeps 14 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
57 reviews(57 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