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Bridle Path House, Quiet Lovely Neighborhood, Porch and Deck Areas, Large Yard, Central Location to all 3 Down Island Towns and Beaches

Lovely 3 bedroom 3 bath home sleeps 8, bordered by a large landscaped yard. The exterior features a shady wrap-around porch with rockers, a perfect place to relax, read a book,  and enjoy...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$5,100 - $6,500
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
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$5,100
13
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$5,100
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26
$5,900
27
28
29
30
 $5,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,900
4
5
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10
$5,900
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$5,900
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$5,900
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$5,900
August 2027
SuMoTuWeThFrSaWeek
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$6,500
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$6,500
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$6,500
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$6,500
29
30
31
 
September 2027
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Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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ROS22

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Property Details

Set in the heart of Oak Bluffs and on a quiet residential street, this newly updated tastefully decorated vacation home offers rental guests all the comforts of home inside and out....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $6,500
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$4,500
6
7
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12
$4,500
13
14
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19
$4,500
20
21
22
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25
26
$4,500
27
28
29
30
 $5,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,500
4
5
6
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$5,500
11
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$5,500
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19
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$5,500
25
26
27
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30
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$5,500
August 2027
SuMoTuWeThFrSaWeek
1
2
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$6,500
8
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$6,500
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$6,500
22
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$6,500
29
30
31
 $5,000
September 2027
SuMoTuWeThFrSaWeek
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2
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$5,000
5
6
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$5,000
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$5,000
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20
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25
$5,000
26
27
28
29
30
 $5,000
Clean Fee: 
$380 per week
Tax: State & Local: 
11.7
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BOOND

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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 - $6,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,200
13
14
15
16
17
18
19
$4,200
20
21
22
23
24
25
26
$4,200
27
28
29
30
 $5,200
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,200
4
5
6
7
8
9
10
$5,200
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
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7
$6,500
8
9
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11
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$6,500
15
16
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18
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21
$6,500
22
23
24
25
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27
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$6,000
29
30
31
 $5,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
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$5,000
12
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$4,000
19
20
21
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23
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25
$4,000
26
27
28
29
30
 $4,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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MACFC

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Property Details
Beautiful Newly Renovated Katama Area Home. Multiple Indoor, Outdoor Living Spaces, Sleeps 8.

Nestled within the scenic Katama area of Edgartown, this home boasts a spacious layout and exquisite renovations, complemented by professional decor. Its prime location offers easy access to both Edgartown...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,500 - $6,500
June 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

 

 

 

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SWEEC

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Property Details
Lovely Updated Cape Style Home, Beautifully Landscaped Yard, Deck & Patio with Multiple Seating Areas & Outdoor Dining

Nestled in a peaceful lane in Edgartown's desirable Dodger’s Hole Area, this charming Cape-style home offers a central location with easy access to Edgartown, Oak Bluffs, Vineyard Haven, and several...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,500 - $6,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
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10
11
12
$3,000
13
14
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$3,500
20
21
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$4,000
27
28
29
30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
4
5
6
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9
10
$4,500
11
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$4,500
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19
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$4,500
25
26
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30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
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$6,500
8
9
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$6,500
15
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$6,500
22
23
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25
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$4,500
29
30
31
 $4,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,500
5
6
7
8
9
10
11
$3,500
12
13
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$3,000
19
20
21
22
23
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25
$2,500
26
27
28
29
30
 $2,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner reduced rates for available weeks in June - see calendar for adjusted rates

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CLEME

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Property Details
Sweetened Water Farm, 1 Mile from Village Center, Bike or Walk to Town

Lovely 4 bedroom, 2 bath home.  Located just on the outskirts of Edgartown village center on Sweetened Water Farm (an 87-acre horse farm located near Morning Glory Farm).  This spacious...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,500 - $6,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 $5,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,500
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
$5,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,200
8
9
10
11
12
13
14
$6,200
15
16
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18
19
20
21
$6,200
22
23
24
25
26
27
28
$6,200
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
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10
11
$3,000
12
13
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18
$3,000
19
20
21
22
23
24
25
$3,000
26
27
28
29
30
 $3,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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CLARO

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Property Details
Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch & Farmers Porch, Deck, Lovely Yard Area, Bike or Walk to Oak Bluffs Center.

Contemporary Farmhouse Design | Multiple Living Areas | Screened Porch, Farmer’s Porch & Deck | Walk or Bike to Oak Bluffs Center

Located just on the outskirts of Oak Bluffs,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,100 - $6,100
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,300
6
7
8
9
10
11
12
$3,300
13
14
15
16
17
18
19
$3,600
20
21
22
23
24
25
26
$4,300
27
28
29
30
 $5,300
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,300
4
5
6
7
8
9
10
$5,300
11
12
13
14
15
16
17
$5,300
18
19
20
21
22
23
24
$5,300
25
26
27
28
29
30
31
$5,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,100
8
9
10
11
12
13
14
$6,100
15
16
17
18
19
20
21
$5,900
22
23
24
25
26
27
28
$5,000
29
30
31
 $3,600
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,600
5
6
7
8
9
10
11
$3,600
12
13
14
15
16
17
18
$3,100
19
20
21
22
23
24
25
$3,100
26
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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LONGK

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Property Details
Bayes Hill Beauty - Stunning Landscaping, Privately Situated Deck & Patio Association Tennis

Note: Caretaker lives in apartment above the garage. Renter's privacy respected.  Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$6,000 - $6,000
June 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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FRISD

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Property Details
Adorable, Chic In -Town Home, Coastal Décor, Central AC, Large Bluestone Patio plus a Farmers Porch for Summer Outdoor Enjoyment

Charming is the description for this newly furnished in-town summer cottage-style home. The house boasts multiple outdoor living spaces, including a large, secluded bluestone patio with an outdoor living room, a patio dining and grill...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $6,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$3,800
13
14
15
16
17
18
19
$3,900
20
21
22
23
24
25
26
$4,600
27
28
29
30
 $5,100
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,100
4
5
6
7
8
9
10
$6,000
11
12
13
14
15
16
17
$6,000
18
19
20
21
22
23
24
$6,000
25
26
27
28
29
30
31
$6,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000
8
9
10
11
12
13
14
$6,000
15
16
17
18
19
20
21
$6,000
22
23
24
25
26
27
28
$5,000
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$3,800
12
13
14
15
16
17
18
$3,800
19
20
21
22
23
24
25
$3,800
26
27
28
29
30
 $3,800
Clean Fee: 
$390 per week
Tax: State & Local: 
11.7
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CENCP

Inquire
Property Details
East Chop Waterfront, Extraordinary Sunsets &Views Across the Sound , Deck directly on the Beach, Casual Interior

Classic, casual beachfront home combines cottage styling with modern amenities. spectacular views, quietly lapping waves right outside your windows, and breathtaking sunsets. Ideally located in the East Chop Area of Oak Bluffs just a short distance...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$6,000 - $6,000
June 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

 

 

 

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DAWKN

Inquire
Property Details
Exquisite Designer Home, 10 minute Walk to Oak Bluffs Town Center, Screened Porch, Patio Dining Area, Landscaped Yard, Professionally Decorated, AC

Quietly nestled on a quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,050 - $6,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,300
6
7
8
9
10
11
12
$5,300
13
14
15
16
17
18
19
$5,300
20
21
22
23
24
25
26
$5,400
27
28
29
30
 $6,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,000
4
5
6
7
8
9
10
$6,000
11
12
13
14
15
16
17
$6,000
18
19
20
21
22
23
24
$6,000
25
26
27
28
29
30
31
$6,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000
8
9
10
11
12
13
14
$6,000
15
16
17
18
19
20
21
$6,000
22
23
24
25
26
27
28
$6,000
29
30
31
 $6,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,000
5
6
7
8
9
10
11
$5,100
12
13
14
15
16
17
18
$5,100
19
20
21
22
23
24
25
$5,100
26
27
28
29
30
 $5,100
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ROBIH

Inquire
Property Details
Seaview Condo Unit, Gorgeous Water Views, In Town Location, Modern updated Interior!

Note: Seaview 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 do...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,100 - $6,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $5,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,000
4
5
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$5,000
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$5,000
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$5,000
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$5,800
August 2027
SuMoTuWeThFrSaWeek
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$6,000
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$7,200
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$7,200
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$5,000
29
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 $2,950
September 2027
SuMoTuWeThFrSaWeek
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$2,950
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$2,950
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$2,950
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$2,950
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 $2,950
Clean Fee: 
$300 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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GRILJ

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Property Details
Lovely Custom Post & Beam Home, Tucked on Gorgeous Private Acreage, 1.5 Miles from the Center of Vineyard Haven.

Martha’s Vineyard Vacation Rental – Private Vineyard Haven Retreat

This lovely and spacious Martha’s Vineyard vacation rental offers all the comforts of home in a serene, private setting. Set on...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,700 - $6,000
June 2027
SuMoTuWeThFrSaWeek
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$3,000
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$3,000
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$3,000
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 $4,800
July 2027
SuMoTuWeThFrSaWeek
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2
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$4,800
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$4,800
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$4,800
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$4,800
25
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$5,500
August 2027
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$5,200
29
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 $3,500
September 2027
SuMoTuWeThFrSaWeek
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$3,500
5
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$3,000
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$3,000
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$3,000
26
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 $3,000
Clean Fee: 
$575
Tax: State & Local: 
11.7
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SAUNJ

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Property Details
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$2,500 - $6,000
June 2027
SuMoTuWeThFrSa
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September 2027
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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FERGN

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Property Details
5 minute walk to town center.

Enjoy a view of Vineyard Haven harbor from this 1898 Captain's home. Walk to town, tennis, dining, library, etc... The Captain Henry Stevenson house has been renovated to include a...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$5,900 - $5,900
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

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