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North Slope Hilltop House. Private yard, Screeened Porch and Patio, 8 minute drive to Lucy Vincent Beach or Menemsha Village

Delightful, 3 bedroom, 2 bath home with AC. Private Chilmark hilltop location! This sweet home features an open kitchen, living, and dining area, and a screened porch for your summer...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
$3,600
15
16
17
18
19
20
21
$3,600
22
23
24
25
26
27
28
$3,800
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
$3,800
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
$4,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
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
$3,600
28
29
30
 $3,600
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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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:
$10 - $4,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,500
22
23
24
25
26
27
28
$5,600
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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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:
$10 - $4,100
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,600
8
9
10
11
12
13
14
$3,600
15
16
17
18
19
20
21
$3,600
22
23
24
25
26
27
28
$3,600
29
30
 $4,100
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,100
6
7
8
9
10
11
12
$4,100
13
14
15
16
17
18
19
$4,100
20
21
22
23
24
25
26
$4,100
27
28
29
30
31
 $4,100
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,100
3
4
5
6
7
8
9
$4,100
10
11
12
13
14
15
16
$4,100
17
18
19
20
21
22
23
$4,100
24
25
26
27
28
29
30
$3,910
31
 $3,660
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,660
7
8
9
10
11
12
13
$3,660
14
15
16
17
18
19
20
$3,660
21
22
23
24
25
26
27
$2,460
28
29
30
 $2,460
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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PHOUE

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Property Details
Sweet Cape Home, Gorgeous Water Views, Walk to Town, Lovely Landscaped Yard, Deck and Outdoor Dining Area.

Note: New Updates for 2025 Rental Season Season: New photos of the upgrades will not be posted until mid-January 2025:

2nd Level balcony/deck seen in photos removed so that primary bedroom...Read more

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

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Property Details
Cozy Contemporary Home with Designer Interior Details , Centrally Located to Towns and Beaches

WELCOME TO SANDPIPER COTTAGE, YOUR STYLISH FAMILY RETREAT!

Four bedrooms include a primary bedroom with a queen bed on the 1st level with a television and a full bath across the...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $3,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,600
8
9
10
11
12
13
14
$2,600
15
16
17
18
19
20
21
$2,800
22
23
24
25
26
27
28
$3,200
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
$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
$3,200
31
 $2,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,800
7
8
9
10
11
12
13
$2,600
14
15
16
17
18
19
20
$2,600
21
22
23
24
25
26
27
$1,600
28
29
30
 $1,600
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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PIN15

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Property Details
Beautiful Oak Bluffs Home, Screened Porch & Open Porch, Association Tennis Courts, 4 bedrooms, 3.5 baths, Ideally Located just 2 miles to Town and Beach

Spacious contemporary home nestled in the lovely community of homes Meadow View Farms just on the outskirts of Oak Bluffs and 2 miles to town center and Oak Bluffs beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $11,750
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,750
8
9
10
11
12
13
14
$9,750
15
16
17
18
19
20
21
$9,750
22
23
24
25
26
27
28
$9,750
29
30
 $11,750
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,750
6
7
8
9
10
11
12
$11,750
13
14
15
16
17
18
19
$11,750
20
21
22
23
24
25
26
$11,750
27
28
29
30
31
 $11,750
August 2025
SuMoTuWeThFrSaWeek
 1
2
$11,750
3
4
5
6
7
8
9
$11,750
10
11
12
13
14
15
16
$11,750
17
18
19
20
21
22
23
$11,750
24
25
26
27
28
29
30
$11,750
31
 $11,750
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$11,750
7
8
9
10
11
12
13
$9,750
14
15
16
17
18
19
20
$9,750
21
22
23
24
25
26
27
$9,750
28
29
30
 $6,820
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PIZZD

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Property Details
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:
$10 - $6,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$3,300
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$5,100
29
30
 $5,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,200
6
7
8
9
10
11
12
$5,700
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,200
27
28
29
30
31
 $6,400
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,400
3
4
5
6
7
8
9
$6,500
10
11
12
13
14
15
16
$6,500
17
18
19
20
21
22
23
$6,500
24
25
26
27
28
29
30
$6,000
31
 $5,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
7
8
9
10
11
12
13
$3,300
14
15
16
17
18
19
20
$2,900
21
22
23
24
25
26
27
$2,900
28
29
30
 $2,600
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PLACH

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Property Details

Note:  Pool is heated by solar panels so the temperature cannot be set. Generally is in the 80's during the latter part of June through the first week of September.  ...Read more

Location: 
Chilmark
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$25,000
8
9
10
11
12
13
14
$25,000
15
16
17
18
19
20
21
$30,000
22
23
24
25
26
27
28
$30,000
29
30
 $40,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$40,000
6
7
8
9
10
11
12
$40,000
13
14
15
16
17
18
19
$40,000
20
21
22
23
24
25
26
$40,000
27
28
29
30
31
 $40,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$40,000
3
4
5
6
7
8
9
$40,000
10
11
12
13
14
15
16
$40,000
17
18
19
20
21
22
23
$40,000
24
25
26
27
28
29
30
$40,000
31
 $30,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$30,000
7
8
9
10
11
12
13
$30,000
14
15
16
17
18
19
20
$25,000
21
22
23
24
25
26
27
$25,000
28
29
30
 $25,000
Clean Fee: 
$800 per week
Tax: State & Local: 
11.7
Add Favorite
 
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POHOD

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Property Details
Eagles Nest, Set on a Quiet Cul-de-Sac, Large Deck, Central A/C

Lovely open concept 3 bedroom, 2 full bath home on a quiet cul de sac in popular Dodger’s Hole neighborhood, steps to bike paths, and public transportation.  Dodger’s Hole is centrally...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $10
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
 $3,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,800
3
4
5
6
7
8
9
$3,800
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
$3,800
31
 $3,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,600
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: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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POWDA

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Property Details
Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$10 - $9,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000
8
9
10
11
12
13
14
$6,500
15
16
17
18
19
20
21
$7,000
22
23
24
25
26
27
28
$7,500
29
30
 $8,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,500
6
7
8
9
10
11
12
$8,500
13
14
15
16
17
18
19
$8,500
20
21
22
23
24
25
26
$9,000
27
28
29
30
31
 $9,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$9,000
3
4
5
6
7
8
9
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$10,000
24
25
26
27
28
29
30
$10,000
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

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