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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Lovely Oak Bluffs Home, 3 Bedrooms, 2.5 Baths, Sleeps 7. Set just on the Outskirts of Oak Bluffs Center

Lovely 3 bedroom, 2.5 bath home that sleeps 7. This sweet home is bordered by a large yard and is located just on the outskirts of Oak Bluffs. The patio...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$2,500 - $4,700
June 2025
SuMoTuWeThFrSaWeek
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 $4,500
July 2025
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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 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
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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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$4,000
31
 $4,700
September 2025
SuMoTuWeThFrSaWeek
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$4,700
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$3,000
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$3,000
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$3,000
28
29
30
 $2,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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DONOP

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Property Details
Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi

Centrally located in the Hidden Cove community of homes on the outskirts of Oak Bluffs. Lovely area to bike, walk, or play tennis at the association courts. 

The main level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,400 - $4,500
June 2025
SuMoTuWeThFrSaWeek
1
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 $4,000
July 2025
SuMoTuWeThFrSaWeek
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$4,000
6
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$4,000
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$4,200
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$4,200
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28
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 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
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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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25
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29
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$3,400
31
 $2,600
September 2025
SuMoTuWeThFrSaWeek
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$2,600
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$2,600
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$2,600
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$2,600
28
29
30
 $2,600
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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VANAL

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Property Details
Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,

Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $4,500
June 2025
SuMoTuWeThFrSaWeek
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 $5,000
July 2025
SuMoTuWeThFrSaWeek
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$5,000
6
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$4,500
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$4,500
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$4,500
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28
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31
 $6,500
August 2025
SuMoTuWeThFrSaWeek
 1
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$6,500
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$6,500
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$6,500
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$7,500
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29
30
$4,500
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
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$4,500
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$3,000
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$3,000
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$3,000
28
29
30
 $3,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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ROLAJ

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Property Details
Waterfront, Water View, Lagoon Beach

This charming, recently renovated, waterfront home atop the lagoon bluffs, boasts spectacular sunsets and panoramic waterfront views of the Lagoon, outer Vineyard Haven Harbor, and Cape Cod from patios, living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,000 - $4,200
June 2025
SuMoTuWeThFrSaWeek
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25
26
27
28
29
30
 $6,200
July 2025
SuMoTuWeThFrSaWeek
 1
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3
4
5
$6,200
6
7
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12
$6,200
13
14
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$6,200
20
21
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$6,200
27
28
29
30
31
 $6,300
August 2025
SuMoTuWeThFrSaWeek
 1
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$6,300
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$6,300
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$6,300
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$6,300
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$5,800
31
 $5,900
September 2025
SuMoTuWeThFrSaWeek
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$5,900
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$4,200
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$4,200
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$4,200
28
29
30
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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PETEV

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Property Details
Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association Tennis Courts, AC, Wi-fi, Bike Paths Nearby

Note: Pricing for this waterfront home takes into account that this is an older-style home. Please note that baths and kitchen have not been updated

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,460 - $4,100
June 2025
SuMoTuWeThFrSaWeek
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 $4,100
July 2025
SuMoTuWeThFrSaWeek
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$4,100
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$4,100
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$4,100
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$4,100
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31
 $4,100
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,100
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$4,100
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$4,100
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$4,100
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$3,910
31
 $3,660
September 2025
SuMoTuWeThFrSaWeek
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$3,660
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$3,660
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$3,660
21
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26
27
$2,460
28
29
30
 $2,460
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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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 - $4,100
June 2025
SuMoTuWeThFrSaWeek
1
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12
13
14
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25
26
27
28
29
30
 $6,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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5
$6,500
6
7
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12
$6,500
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$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
31
 $6,400
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,400
3
4
5
6
7
8
9
$6,600
10
11
12
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14
15
16
$6,600
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18
19
20
21
22
23
$6,600
24
25
26
27
28
29
30
$6,600
31
 $6,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,600
7
8
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13
$4,100
14
15
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20
$4,100
21
22
23
24
25
26
27
$4,100
28
29
30
 $2,600
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Rate reduced for week 7/11-7/18 - see calendar for adjusted rates

 

Owner books Fri to Fri July & August weeks!

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CENCR

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Property Details
Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Great Area for Kayaking.

Spacious sun-filled home features open living spaces, hardwood floors throughout, 4 bedrooms and sleeps 8.

Exterior features include two decks, one sunny deck at the front of the house, and a large private...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
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10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 $4,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,800
6
7
8
9
10
11
12
$4,800
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$5,200
27
28
29
30
31
 $5,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,800
3
4
5
6
7
8
9
$8,800
10
11
12
13
14
15
16
$9,900
17
18
19
20
21
22
23
$11,800
24
25
26
27
28
29
30
$5,800
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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6
$4,000
7
8
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13
$4,000
14
15
16
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18
19
20
$3,500
21
22
23
24
25
26
27
$3,000
28
29
30
 $3,000
Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

Ferry Ticket Available 8/10 week. (mv) Please inquire for details. 

Rate reduced for week of 8/10 due to a cancellation - see calendar for adjusted rate

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CAH48

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Property Details
Classic Lovely Vineyard Cottage, Pristine Condition, Approximately 1.5 Miles to Town and Beaches. Mature Landscaped Yard, Spacious Deck

The Perfect Cozy Cottage, is pristinely maintained and situated in a quiet neighborhood just on the outskirts of Oak Bluffs.  This spacious 2 bedroom, 2 bath home sleeps 4. The...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,700 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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10
11
12
13
14
15
16
17
18
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20
21
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23
24
25
26
27
28
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
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18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
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$4,000
17
18
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23
$4,000
24
25
26
27
28
29
30
$4,000
31
 $2,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,700
7
8
9
10
11
12
13
$2,700
14
15
16
17
18
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20
$2,700
21
22
23
24
25
26
27
$2,700
28
29
30
 
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
11.7
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THORB

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Property Details
Contemporary 5 Bedroom 4 Bath, Multiple Living Spaces, Walk to Oak Bluffs Center and Inkwell Beach-10 minutes

Extended families are sure to enjoy this tri-level home featuring an open floor plan on the main level, a large main living room, and three den/TV areas, one on the first level...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$2,700 - $3,800
June 2025
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
25
26
27
28
29
30
 $6,100
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,100
6
7
8
9
10
11
12
$6,100
13
14
15
16
17
18
19
$6,100
20
21
22
23
24
25
26
$6,300
27
28
29
30
31
 $6,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,600
3
4
5
6
7
8
9
$6,600
10
11
12
13
14
15
16
$6,600
17
18
19
20
21
22
23
$6,600
24
25
26
27
28
29
30
$5,900
31
 $3,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,800
7
8
9
10
11
12
13
$3,800
14
15
16
17
18
19
20
$3,800
21
22
23
24
25
26
27
$3,800
28
29
30
 $2,700
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ROBIH

(0)Inquire/Share
Property Details
Seaview Condo Unit, Gorgeous Water Views, In Town Location, Modern updated Interior!

Note: Seavies Condos is a 3-minute walk from the Steamship Authority dock in Oak Bluffs and two blocks from the Island Queen ferry dock. Perfect location if you cannot or...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$1,950 - $3,800
June 2025
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
25
26
27
28
29
30
 $3,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,800
6
7
8
9
10
11
12
$3,800
13
14
15
16
17
18
19
$3,800
20
21
22
23
24
25
26
$4,500
27
28
29
30
31
 
August 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
$5,100
10
11
12
13
14
15
16
$5,100
17
18
19
20
21
22
23
$5,100
24
25
26
27
28
29
30
$3,800
31
 $2,550
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,550
7
8
9
10
11
12
13
$2,550
14
15
16
17
18
19
20
$1,950
21
22
23
24
25
26
27
$1,950
28
29
30
 $1,950
Clean Fee: 
$230 per week
Tax: State & Local: 
11.7

5 minute walk from Steamship Authority Oak Bluffs dock to the Seaview Condos.  2 blocks from the Island Queen ferry dock.  

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KNOXA

(0)Inquire/Share
Property Details
Modern Cottage, Recently Updated! Walk to Oak Bluffs Harbor and Town Center, 15 min walk

Walk to Oak Bluffs town center, ferry, or Inkwell Beach from this beach-chic recently renovated, adorable cottage! 

Upon entering you are greeted with an open floor plan in the living, kitchen,...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$3,150 - $3,800
June 2025
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
25
26
27
28
29
30
 $3,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,600
6
7
8
9
10
11
12
$3,600
13
14
15
16
17
18
19
$3,600
20
21
22
23
24
25
26
$3,600
27
28
29
30
31
 $4,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,900
3
4
5
6
7
8
9
$7,000
10
11
12
13
14
15
16
$7,000
17
18
19
20
21
22
23
$4,200
24
25
26
27
28
29
30
$3,800
31
 $3,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,600
7
8
9
10
11
12
13
$3,600
14
15
16
17
18
19
20
$3,600
21
22
23
24
25
26
27
$3,600
28
29
30
 $3,150
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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FRANL

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Property Details
Modern, Light filled Home, Located at end of Quiet Street, 1.5 Miles to Oak Bluffs center, Harbor Area and one of many Public Beaches

Perfect Oak Bluffs vacation home.  Located just 1.5 miles to the village center, town beach, and centrally located to the towns of Vineyard Haven, Edgartown, and multiple public beaches.  This...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$2,300 - $3,600
June 2025
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
25
26
27
28
29
30
 $3,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,600
6
7
8
9
10
11
12
$3,600
13
14
15
16
17
18
19
$3,600
20
21
22
23
24
25
26
$3,600
27
28
29
30
31
 $3,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,600
3
4
5
6
7
8
9
$3,600
10
11
12
13
14
15
16
$3,600
17
18
19
20
21
22
23
$3,600
24
25
26
27
28
29
30
$3,300
31
 $2,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,800
7
8
9
10
11
12
13
$2,800
14
15
16
17
18
19
20
$2,800
21
22
23
24
25
26
27
$2,800
28
29
30
 $2,300
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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SACHE

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Property Details
Waterview Farms, Water view

Lovely contemporary home in one of the island's premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $3,500
June 2025
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
25
26
27
28
29
30
 $3,500
July 2025
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
$3,500
27
28
29
30
31
 $3,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,500
3
4
5
6
7
8
9
$3,800
10
11
12
13
14
15
16
$3,800
17
18
19
20
21
22
23
$3,800
24
25
26
27
28
29
30
$3,800
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$3,500
28
29
30
 $3,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MAHAB

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Property Details
Sweet Updated 3 Bedroom Home, Nicely Tucked in Lightly Wooded Area, Central Location, Beaches and Towns just a short Drive!

Lovely reverse contemporary home with a large deck, outdoor dining, and grill area. The upper level of this home features an open kitchen, living, and dining area stylishly furnished.  Nicely equipped kitchen...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$3,500 - $3,500
June 2025
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
25
26
27
28
29
30
 $4,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
12
13
14
15
16
$4,000
17
18
19
20
21
22
23
$4,000
24
25
26
27
28
29
30
$3,500
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$3,500
28
29
30
 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PETEO

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Property Details
Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully Landscaped

Outstanding vacation home, centrally located to all three down-island town centers and multiple public beaches. This lovely home in a serene setting overlooks the picturesque Little Duarte Pond in the Iron Hill...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
5
Price Range:
$3,400 - $3,400
June 2025
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
25
26
27
28
29
30
 $6,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,200
6
7
8
9
10
11
12
$6,200
13
14
15
16
17
18
19
$6,200
20
21
22
23
24
25
26
$6,700
27
28
29
30
31
 $7,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,200
3
4
5
6
7
8
9
$7,600
10
11
12
13
14
15
16
$7,600
17
18
19
20
21
22
23
$7,600
24
25
26
27
28
29
30
$6,500
31
 $3,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,900
7
8
9
10
11
12
13
$3,400
14
15
16
17
18
19
20
$3,400
21
22
23
24
25
26
27
$3,400
28
29
30
 
Clean Fee: 
$575 per week
Tax: State & Local: 
11.7

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