Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Beautiful Oak Bluffs home just blocks from the Center of Town, Ocean Park and Inkwell Beach.

Note: the kitchen is being completely remodeled for summer 2024 and will have all new high-end appliances, Subzero, Thermador, and new cabinets, and counters. 

Summer Joy!  Set in the heart of...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$5,750 - $9,150
June 2027
SuMoTuWeThFrSaWeek
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$5,900
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$5,900
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$8,000
27
28
29
30
 $8,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$8,250
4
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10
$8,400
11
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$8,500
18
19
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$8,500
25
26
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30
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$8,500
August 2027
SuMoTuWeThFrSaWeek
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$9,150
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$9,150
15
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21
$9,150
22
23
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25
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27
28
$9,150
29
30
31
 $6,900
September 2027
SuMoTuWeThFrSaWeek
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2
3
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$6,900
5
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$6,900
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$6,900
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$6,900
26
27
28
29
30
 $6,900
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

8-minute walk from the ferry dock in Oak Bluffs and 5 minute walk to the Ink Well Beach, and Oak Bluffs Center from the house. 

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WHARG

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Property Details
Lovely Home in a quiet Neighborhood. Walk to Town Center and Inkwell Beach, Large Private Deck, Room AC

Spacious sun-filled contemporary home located on a quiet private street, a 10-minute walk to town center, Inkwell Beach, and the harborfront.

The first level features a spacious kitchen with stainless steel...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$7,200 - $8,500
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
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$7,200
6
7
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$7,200
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$7,200
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25
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$7,200
27
28
29
30
 $7,200
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$7,200
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5
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10
$7,500
11
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$7,500
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19
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$7,500
25
26
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29
30
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$7,500
August 2027
SuMoTuWeThFrSaWeek
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$8,500
8
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$8,500
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$8,500
22
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$8,500
29
30
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 $8,500
September 2027
SuMoTuWeThFrSaWeek
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$8,500
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Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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BOWDL

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Property Details
Lovely Custom Contemporary Home, Tucked in the Community of Bayes Hill, 4 Bedrooms, 4 Bath, Landscaped, Deck, Patio Dining Area

Designed with a sophisticated contemporary aesthetic, this chic vacation retreat showcases an open floor plan, expansive windows, and beautifully curated interiors. Offering four bedrooms and 3.5 baths, the home is...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $8,050
June 2027
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$7,500
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$7,500
27
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 $7,750
July 2027
SuMoTuWeThFrSaWeek
 1
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$7,750
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$7,750
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$7,750
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$7,750
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$8,050
August 2027
SuMoTuWeThFrSaWeek
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$8,050
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$8,050
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$8,050
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$8,050
29
30
31
 $8,050
September 2027
SuMoTuWeThFrSaWeek
 1
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$8,050
5
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$7,500
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$7,500
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$7,500
26
27
28
29
30
 $7,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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BEG21

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Property Details
Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $8,000
June 2027
SuMoTuWeThFrSaWeek
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$4,500
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$4,500
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$4,500
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$4,500
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 $6,500
July 2027
SuMoTuWeThFrSaWeek
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$6,500
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$7,000
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$7,000
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$7,000
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$7,000
August 2027
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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$8,000
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$8,000
29
30
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 $3,500
September 2027
SuMoTuWeThFrSaWeek
 1
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$3,500
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$3,500
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$3,500
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$3,500
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Note: Owner maintains security camera on front of house

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JOHNL

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Property Details
"Endless Summer Vacation" Stylish, Newly Updated 3 + Bedroom, Sleeps 8, East Chop Area of Oak Bluffs, Deck Living & Dining Area, Screened Porch
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $8,000
June 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,000
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 $5,250
July 2027
SuMoTuWeThFrSaWeek
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$5,250
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$5,250
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$5,250
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$5,250
25
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$5,750
August 2027
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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$8,000
22
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$8,000
29
30
31
 $5,000
September 2027
SuMoTuWeThFrSaWeek
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$5,000
5
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$5,000
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$5,000
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$5,000
26
27
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29
30
 $5,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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BURBR

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Property Details
Perfect Retreat for Large Families, 1.5 miles to Oak Bluffs Town Center & Beach, Bike Path at end of Street

Spacious and perfect for extended families, featuring multiple attractively furnished living areas, and sleeps 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with...Read more

Location: 
Oak Bluffs
Sleeps: 
11
Bedrooms: 
5
Baths: 
3
Price Range:
$7,950 - $7,950
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSaWeek
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$7,950
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$7,950
August 2027
SuMoTuWeThFrSaWeek
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$7,950
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$7,950
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$7,950
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$7,950
29
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 $7,950
September 2027
SuMoTuWeThFrSaWeek
 1
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$7,950
5
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$7,950
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$7,950
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$7,950
26
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29
30
 $7,950
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner reduced rates for weeks 7/12 & 8/23 by 20% - see calendar for adjusted rate

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CASHK

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Property Details
Lovely Home, Centrally Located, Bike Paths, AC all Rooms

This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window AC in all rooms, and a well-equipped modern kitchen. The home is nicely situated...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$7,500 - $7,800
June 2027
SuMoTuWeThFrSaWeek
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 $7,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$7,500
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$7,500
11
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$7,500
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$7,500
25
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$7,500
August 2027
SuMoTuWeThFrSaWeek
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$7,800
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$7,800
15
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$7,800
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$7,800
29
30
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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LIJOY

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Property Details
Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, Bike Paths at Entrance to Neighborhood, Multiple Beaches Near By

Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,700 - $7,800
June 2027
SuMoTuWeThFrSaWeek
 1
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30
 $6,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,800
4
5
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10
$7,200
11
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$7,000
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$7,000
25
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$7,300
August 2027
SuMoTuWeThFrSaWeek
1
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$7,300
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$7,800
15
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$7,800
22
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$7,300
29
30
31
 $6,800
September 2027
SuMoTuWeThFrSaWeek
 1
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$6,800
5
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$7,000
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29
30
 
Clean Fee: 
$420 per week
Tax: State & Local: 
11.7
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INGAE

Inquire
Property Details
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,250 - $7,750
June 2027
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July 2027
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September 2027
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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TRAVM

Inquire
Property Details
Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.

Visitors will enjoy this delightful &  comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. 

Relax in the breeze with your morning coffee on the front...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$5,350 - $7,500
June 2027
SuMoTuWeThFrSaWeek
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 $5,350
July 2027
SuMoTuWeThFrSaWeek
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$5,350
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$5,350
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$5,350
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$5,350
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$7,000
August 2027
SuMoTuWeThFrSaWeek
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$7,000
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$7,200
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$7,500
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$7,500
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September 2027
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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TERSM

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Property Details
Modern, Newly Renovated, Architecturally Significant Beach Cottage Design. Close to Town and Beaches, Tucked in the Lovely Community of Summer Homes, Waterview Farms!

Gorgeous all newly renovated and newly furnished mid-century beach cottage, now a modern vacation oasis designed by the prominent interior design firm, - Tersigni Palachek. This eloquent, yet beachy home offers...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,600 - $7,200
June 2027
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September 2027
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Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Owner books Fri to Fri July & August weeks!

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BICKE

Inquire
Property Details
East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

East Chop Escape with lovely Distant Water Views
Light-Filled Tri-Level Home, 4 Bedrooms, & 3 baths, 1.5 Miles to Oak Bluffs Center

Set in the highly sought-after East Chop neighborhood,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $7,150
June 2027
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28
29
30
 $7,150
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,150
4
5
6
7
8
9
10
$7,150
11
12
13
14
15
16
17
$7,150
18
19
20
21
22
23
24
$7,150
25
26
27
28
29
30
31
$7,150
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,150
8
9
10
11
12
13
14
$7,150
15
16
17
18
19
20
21
$7,150
22
23
24
25
26
27
28
$7,150
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
7
8
9
10
11
$6,500
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$6,500
26
27
28
29
30
 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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BURBS

Inquire
Property Details
Set Just on the ouskirts of Oak Bluffs. Central AC, Screened Porch

Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs center and beach area.  Fully furnished screen porch and shady porch.  This lovely home sleeps families of 8 comfortably.

The main...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$6,500 - $7,100
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
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25
26
27
28
29
30
 
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
$6,500
25
26
27
28
29
30
31
$6,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,100
8
9
10
11
12
13
14
$7,100
15
16
17
18
19
20
21
$7,100
22
23
24
25
26
27
28
$7,100
29
30
31
 
September 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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HANRJ

Inquire
Property Details
Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes

Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $7,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,800
27
28
29
30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
4
5
6
7
8
9
10
$5,500
11
12
13
14
15
16
17
$5,500
18
19
20
21
22
23
24
$5,500
25
26
27
28
29
30
31
$6,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,000
8
9
10
11
12
13
14
$7,000
15
16
17
18
19
20
21
$7,000
22
23
24
25
26
27
28
$5,500
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$4,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
 $3,500
Clean Fee: 
$575
Tax: State & Local: 
11.7

Rates reduced for available weeks June - September - see calendar for adjusted rates

 

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BOOND

Inquire
Property Details
Wonderful Vacation Home, East Chop Area of Oak Bluffs, Private Yard, Screened Porch, 4 bedrooms, 2 baths.

Nestled on a quiet street in the idyllic East Chop area of Oak Bluffs, this classic New England summer home offers vacationing families and friends a special place to gather...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,000 - $7,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,250
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,750
20
21
22
23
24
25
26
$5,000
27
28
29
30
 $5,750
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,750
4
5
6
7
8
9
10
$6,250
11
12
13
14
15
16
17
$6,250
18
19
20
21
22
23
24
$6,500
25
26
27
28
29
30
31
$6,750
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,250
8
9
10
11
12
13
14
$7,000
15
16
17
18
19
20
21
$7,000
22
23
24
25
26
27
28
$6,500
29
30
31
 $5,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$5,250
12
13
14
15
16
17
18
$4,500
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
 $4,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Linens additonal $250

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