Holiday rentals near Oak Bluffs Harbor
We found 1,674 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:3 Oct - 10 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
9% off
Price is NZ$13,915
NZ$13,915
NZ$1,988 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 NZ$4,178
NZ$4,178
NZ$597 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$8,561
NZ$8,561
NZ$1,223 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 NZ$5,583
NZ$5,583
NZ$798 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 NZ$9,580
NZ$9,580
NZ$1,369 per night
includes taxes & fees
Image gallery for Cozy New TimberFrame Vineyard Haven!
1010 out of 10 rating
Exceptional
(20 reviews)
Cozy New TimberFrame Vineyard Haven!
Vineyard Haven, MA
8% off
Price is NZ$5,484
NZ$5,484
NZ$783 per night
includes taxes & fees
Image gallery for Completely renovated Edgartown cape with New Pool ~ Sleeps 14
1010 out of 10 rating
Exceptional
(19 reviews)
Completely renovated Edgartown cape with New Pool ~ Sleeps 14
Edgartown, MA
8% off
Price is NZ$21,012
NZ$21,012
NZ$3,002 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
14% off
Price is NZ$4,131
NZ$4,131
NZ$590 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
7% off
Price is NZ$11,607
NZ$11,607
NZ$1,658 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$20,177
NZ$20,177
NZ$2,882 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 NZ$8,957
NZ$8,957
NZ$1,280 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 NZ$9,008
NZ$9,008
NZ$1,287 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 NZ$5,514
NZ$5,514
NZ$788 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 NZ$10,189
NZ$10,189
NZ$1,456 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 NZ$9,612
NZ$9,612
NZ$1,373 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 NZ$9,037
NZ$9,037
NZ$1,291 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 NZ$16,677
NZ$16,677
NZ$2,382 per night
includes taxes & fees
Image gallery for Katama Edgartown... bike to South Beach, bike to Town
1010 out of 10 rating
Exceptional
(7 reviews)
Katama Edgartown... bike to South Beach, bike to Town
Edgartown, MA
8% off
Price is NZ$5,964
NZ$5,964
NZ$852 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
(75 reviews)
Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven
Oak Bluffs, MA
8% off
Price is NZ$4,986
NZ$4,986
NZ$712 per night
includes taxes & fees
Image gallery for New 4-bedroom House with Swimming Pool–Just a 10-minute Walk to Town
1010 out of 10 rating
Exceptional
(10 reviews)
New 4-bedroom House with Swimming Pool–Just a 10-minute Walk to Town
Edgartown, MA
5% off
Price is NZ$20,538
NZ$20,538
NZ$2,934 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
(12 reviews)
Secluded, Private Vacation Beach Home on Chappaquiddick Island, Walk To Beach.
Edgartown, MA
8% off
Price is NZ$37,294
NZ$37,294
NZ$5,328 per night
includes taxes & fees
Image gallery for Charming Home Walking Distance to Downtown Vineyard Haven
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Charming Home Walking Distance to Downtown Vineyard Haven
Vineyard Haven, MA
8% off
Price is NZ$10,705
NZ$10,705
NZ$1,529 per night
includes taxes & fees
Image gallery for Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
1010 out of 10 rating
Exceptional
(29 reviews)
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
Oak Bluffs, MA
7% off
Price is NZ$3,556
NZ$3,556
NZ$508 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 NZ$10,454
NZ$10,454
NZ$1,493 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
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
38 reviews(38 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)
WATERFRONT Downtown Cottage w/ Beach
Sleeps 2 · 1 bedroom · 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