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1.5 Acres of Privacy, Bike Paths Adjacent to House, Association Pool, WiFi, Central A/C

West Tisbury - Newly updated and featuring 5 bedrooms and 4 baths.  Recently renovated including all new kitchen, updated baths, flooring, carpeting, walls painted, and lovely furnishings.  There is central AC on the 1st...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$3,500 - $6,500
June 2026
SuMoTuWeThFrSaWeek
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2
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4
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$4,000
7
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$4,000
14
15
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$4,000
21
22
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26
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$5,000
28
29
30
 $5,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$5,900
5
6
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10
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$6,250
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$6,250
19
20
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22
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24
25
$6,500
26
27
28
29
30
31
 $6,500
August 2026
SuMoTuWeThFrSaWeek
 1
$6,500
2
3
4
5
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8
$6,500
9
10
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15
$6,500
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17
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21
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$6,500
23
24
25
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27
28
29
$6,500
30
31
 $5,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,900
6
7
8
9
10
11
12
$4,900
13
14
15
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18
19
$4,900
20
21
22
23
24
25
26
$4,900
27
28
29
30
 $3,900
Clean Fee: 
$450 per week, $500 per week with pet
Tax: State & Local: 
11.7
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KATAMA AREA, SET ON PRIVATE ACREAGE, SHORT DRIVE TO SOUTH BEACH AND EDGARTOWN VILLAGE CENTER

Extended family will enjoy the comfort and private setting of this large 5 bedroom home in the Katama area of Edgartown.   Spacious for extended family, the kitchen with custom cabinetry and...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$2,400 - $6,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
7
8
9
10
11
12
13
$3,300
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$5,100
28
29
30
 
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
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12
13
14
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18
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21
22
23
24
25
$6,200
26
27
28
29
30
31
 $6,400
August 2026
SuMoTuWeThFrSaWeek
 1
$6,400
2
3
4
5
6
7
8
$6,500
9
10
11
12
13
14
15
$6,500
16
17
18
19
20
21
22
$6,500
23
24
25
26
27
28
29
$6,000
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$3,300
13
14
15
16
17
18
19
$2,900
20
21
22
23
24
25
26
$2,900
27
28
29
30
 $2,600
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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Beautifully Updated and Newly Furnished, 4 Bedrooms, 3 Baths, Multiple Living Spaces, Centrally Located to Down Island Towns and Beaches.

This charming newly renovated home boasts an airy, open floor plan on the main level featuring a wall of glass sliders that open onto a spacious deck area complete with a...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $6,500
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
 1
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14
15
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20
21
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23
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27
28
29
30
31
 $6,500
August 2026
SuMoTuWeThFrSaWeek
 1
$6,500
2
3
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5
6
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$6,500
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$7,000
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$7,000
23
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29
$6,500
30
31
 $4,500
September 2026
SuMoTuWeThFrSaWeek
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2
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$4,500
6
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$3,500
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27
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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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 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$4,200
14
15
16
17
18
19
20
$4,200
21
22
23
24
25
26
27
$4,200
28
29
30
 $5,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,200
5
6
7
8
9
10
11
$5,200
12
13
14
15
16
17
18
$5,500
19
20
21
22
23
24
25
$5,500
26
27
28
29
30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
4
5
6
7
8
$6,500
9
10
11
12
13
14
15
$6,500
16
17
18
19
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21
22
$6,500
23
24
25
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27
28
29
$6,000
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$5,000
6
7
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12
$5,000
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14
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18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $6,500
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSa
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August 2026
SuMoTuWeThFrSaWeek
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$8,500
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$8,500
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$8,500
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24
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$6,500
30
31
 
September 2026
SuMoTuWeThFrSa
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2
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21
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27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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Edgartown Village Center Home, Walk to Town, 2 Bedrooms, 2 Baths

Experience all that Edgartown Village Center has to offer, just a short stroll from this bright and airy home. Additional décor and deck furniture will be added for summer 2025....Read more

Location: 
Edgartown
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$4,000 - $6,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
 $5,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,900
5
6
7
8
9
10
11
$5,900
12
13
14
15
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17
18
$5,900
19
20
21
22
23
24
25
$5,900
26
27
28
29
30
31
 $5,900
August 2026
SuMoTuWeThFrSaWeek
 1
$5,900
2
3
4
5
6
7
8
$6,500
9
10
11
12
13
14
15
$6,500
16
17
18
19
20
21
22
$6,500
23
24
25
26
27
28
29
$6,000
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
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
 $4,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Lovely Home in Island Grove Area of Edgartown Conveniently Located between South Beach and Edgartown Village. Association Tennis Courts and Pickleball Available to Renters

This recently updated home is tucked in the Island Grove area of Edgartown and is a perfect retreat for families & friends to gather. Located in a desirable neighborhood with access...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,280 - $6,470
June 2026
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
$4,800
28
29
30
 $5,280
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,280
5
6
7
8
9
10
11
$5,770
12
13
14
15
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18
$5,770
19
20
21
22
23
24
25
$5,770
26
27
28
29
30
31
 $5,770
August 2026
SuMoTuWeThFrSaWeek
 1
$5,770
2
3
4
5
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8
$6,470
9
10
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12
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September 2026
SuMoTuWeThFrSa
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21
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24
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27
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29
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Clean Fee: 
$525 per week
Tax: State & Local: 
11.7
Add Favorite
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Cozy Cape, Newly Updated Summer 2023, Quiet Private Central Location, 4 Bedrooms, 3 Baths

Enjoy all the comforts of home in this tri-level updated Cape-style home set in a quiet cul de sac and bordered by lovely landscaping and mature oaks.   Multiple living spaces include the...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $6,400
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,200
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$4,800
21
22
23
24
25
26
27
$5,600
28
29
30
 $5,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,700
5
6
7
8
9
10
11
$5,700
12
13
14
15
16
17
18
$5,700
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
4
5
6
7
8
$6,400
9
10
11
12
13
14
15
$6,900
16
17
18
19
20
21
22
$6,900
23
24
25
26
27
28
29
$6,300
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$3,200
13
14
15
16
17
18
19
$3,200
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
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Chic, Meticulously Maintained Cape Style Home, 3 bedrooms, 3 Baths, Sleeps, 6 Walk to Oak Bluffs Town Center and Beaches, Tucked on a Large Beautifully Landscaped Lot

Nestled in a beautifully landscaped lot in a serene and private neighborhood, this meticulously maintained cottage in Oak Bluffs, Martha's Vineyard, offers a perfect retreat for rental guests. With chic...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,750 - $6,350
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,750
7
8
9
10
11
12
13
$3,750
14
15
16
17
18
19
20
$4,350
21
22
23
24
25
26
27
$4,600
28
29
30
 $5,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,400
5
6
7
8
9
10
11
$5,400
12
13
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18
$5,600
19
20
21
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24
25
$5,600
26
27
28
29
30
31
 $5,600
August 2026
SuMoTuWeThFrSaWeek
 1
$5,600
2
3
4
5
6
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8
$6,850
9
10
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15
$6,850
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22
$6,850
23
24
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29
$6,350
30
31
 $3,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,750
6
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$3,750
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$3,750
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21
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$3,750
27
28
29
30
 $3,750
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
Add Favorite
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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 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,500
7
8
9
10
11
12
13
$2,500
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,800
28
29
30
 $5,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$5,500
12
13
14
15
16
17
18
$5,500
19
20
21
22
23
24
25
$5,500
26
27
28
29
30
31
 $5,900
August 2026
SuMoTuWeThFrSaWeek
 1
$5,900
2
3
4
5
6
7
8
$6,200
9
10
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12
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15
$6,200
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17
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21
22
$6,200
23
24
25
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27
28
29
$6,200
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
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10
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12
13
14
15
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17
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20
21
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25
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28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
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Newly Updated Chilmark Cottage, Key to Private association Black Point Beach just 8/10ths mile from Cottage

For those who love Chilmark! Located in a very private setting off of Quenames Rd, this fresh and modern updated cottage comes with a key to private association Black Point...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$3,500 - $6,050
June 2026
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
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $5,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,800
5
6
7
8
9
10
11
$5,800
12
13
14
15
16
17
18
$5,800
19
20
21
22
23
24
25
$5,800
26
27
28
29
30
31
 $6,050
August 2026
SuMoTuWeThFrSaWeek
 1
$6,050
2
3
4
5
6
7
8
$6,050
9
10
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15
$6,050
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17
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21
22
$6,050
23
24
25
26
27
28
29
$6,050
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
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12
$5,000
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 $3,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
lewid13-01-deck.jpg
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Menemsha Waterfront, Magnificent Views and Private Location, WiFi

This quintessential Chilmark cottage/home has been impeccably maintained,  The dining and living areas with spectacular views across Menemsha Channel to Aquinnah open to a wrap-around deck.  Enjoy spectacular water views...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $6,000
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$375 per week, owner will provide sheets, towels, beach towels, additional $225 per rental period
Tax: State & Local: 
11.7

Owner will provide, sheets, towels & beach towels for an additional $225 per rented period. 

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West Chop Area, Central Air

Country Cottage Retreat. This completely renovated gem is located just at the head of the West Chop area in Vineyard Haven. The interior layout features four bedrooms, 2.5 baths, a...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $6,000
June 2026
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
$4,000
28
29
30
 $5,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,800
5
6
7
8
9
10
11
$5,800
12
13
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$5,800
19
20
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23
24
25
$5,800
26
27
28
29
30
31
 $5,800
August 2026
SuMoTuWeThFrSaWeek
 1
$5,800
2
3
4
5
6
7
8
$6,000
9
10
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13
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15
$6,000
16
17
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$6,000
23
24
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29
$6,000
30
31
 $4,250
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,250
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
 $3,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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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 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,300
7
8
9
10
11
12
13
$5,300
14
15
16
17
18
19
20
$5,300
21
22
23
24
25
26
27
$5,400
28
29
30
 $6,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,000
5
6
7
8
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11
$6,000
12
13
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$6,000
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25
$6,000
26
27
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30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
4
5
6
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$6,000
9
10
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$6,000
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$6,000
23
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$6,000
30
31
 $6,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$6,000
6
7
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$5,100
13
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$5,100
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25
26
$5,100
27
28
29
30
 $5,100
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Beautiful Newly Updated Cape Style Home, Association Tennis Courts 2 min Walk, Biking & Hiking Trails, Beaches 10 minutes from House

This lovely 3 bedroom, 2.5 bath home features sun-filled rooms, an open floor plan throughout, screened porch set up as a summer living room with a sectional sofa, and a...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,200 - $6,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,400
7
8
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10
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12
13
$5,400
14
15
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20
$5,400
21
22
23
24
25
26
27
$5,400
28
29
30
 $6,000
July 2026
SuMoTuWeThFrSaWeek
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2
3
4
$6,000
5
6
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$6,000
12
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$6,000
19
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$6,000
26
27
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30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
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$6,000
2
3
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5
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$6,000
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$6,000
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$6,000
23
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$6,000
30
31
 $5,400
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,400
6
7
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12
$5,400
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$5,400
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25
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$5,400
27
28
29
30
 $5,000
Clean Fee: 
$400
Tax: State & Local: 
11.7

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