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 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 £2,272
£2,272
£325 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 £12,120
£12,120
£1,731 per night
includes taxes & fees
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 £3,591
£3,591
£513 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 £6,189
£6,189
£884 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 £1,917
£1,917
£274 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 £8,925
£8,925
£1,275 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 £3,638
£3,638
£520 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 £1,667
£1,667
£238 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 £2,383
£2,383
£340 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
7% off
Price is £3,228
£3,228
£461 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
7% off
Price is £3,189
£3,189
£456 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 £6,596
£6,596
£942 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 £5,050
£5,050
£721 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
7% off
Price is £5,475
£5,475
£782 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
7% off
Price is £3,895
£3,895
£556 per night
includes taxes & fees
Image gallery for One mile from South Cape Beach
1010 out of 10 rating
Exceptional
(36 reviews)
One mile from South Cape Beach
Mashpee, MA
7% off
Price is £2,976
£2,976
£425 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
7% off
Price is £4,874
£4,874
£696 per night
includes taxes & fees
Image gallery for Walk to Town! Beautiful, Private Edgartown Home
1010 out of 10 rating
Exceptional
(28 reviews)
Walk to Town! Beautiful, Private Edgartown Home
Edgartown, MA
7% off
Price is £4,715
£4,715
£674 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
7% off
Price is £4,502
£4,502
£643 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 £9,199
£9,199
£1,314 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
7% off
Price is £4,160
£4,160
£594 per night
includes taxes & fees
Image gallery for Katama / South Beach Beach House
1010 out of 10 rating
Exceptional
(13 reviews)
Katama / South Beach Beach House
Edgartown, MA
8% off
Price is £4,764
£4,764
£681 per night
includes taxes & fees
Image gallery for Elegant Oceanview Home On Triton Way in New Seabury With Heated Pool & beach
1010 out of 10 rating
Exceptional
(44 reviews)
Elegant Oceanview Home On Triton Way in New Seabury With Heated Pool & beach
Mashpee, MA
16% off
Price is £8,675
£8,675
£1,239 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 £2,225
£2,225
£318 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)
Top rated rentals - Oak Bluffs Harbor
Highly recommended
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Lovely cottage, great location and very responsive host.
KUNAL M.
Stayed Jul 2025
Cosy Cottage
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
The property was wonderful. Fresh and immaculately clean throughout. Excellent kitchen. Comfy beds. Lovely living rooms. Amazing location - very peaceful, but so close to all local amenities. Gorgeous beach at the end of the road.
The Host has thought of everything.
Our stay was perfect.
Communication with Nicole was excellent.
Penny B.
Stayed May 2023
Lovely house.
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
A great place to stay. Convenient for all amenities and very well equipped. As a disabled traveler I found the house easy to use although if I was wheelchair bound access would have been difficult. Thank you for a great stay.
Gordon W.
Stayed Sept 2018
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All the privacy of homeEnjoy full kitchens, pools, gardens and more
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