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Your connection to all Martha's Vineyard Real Estate and Vacation Rentals
508-693-7832
Karen M. Overtoom Logo
508-693-7832


Martha's Vineyard Vacation Rentals in Chilmark








Contemporary Beachfront Retreat


"Waterfront on Menemsha Pond!"

Overlooking Menemsha Pond with breathtaking water views from every room of the classic contemporary home with whole house air conditioning, this enchanting Chilmark property sits perched on a rise with a short path down to the beach that is shared with one neighbor. Central to this incredible prope...Read the full description.

JUNE 2026
S M T W T F S Cost
 
1
2
3
4
5
6
CALL
7
8
9
10
11
12
13
CALL
14
15
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18
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20
CALL
21
22
23
24
25
26
27
CALL
28
29
30
        CALL
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
CALL
5
6
7
8
9
10
11
CALL
12
13
14
15
16
17
18
CALL
19
20
21
22
23
24
25
CALL
26
27
28
29
30
31
  CALL
               
AUGUST 2026
S M T W T F S Cost
           
1
CALL
2
3
4
5
6
7
8
CALL
9
10
11
12
13
14
15
CALL
16
17
18
19
20
21
22
CALL
23
24
25
26
27
28
29
CALL
30
31
          CALL.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
CALL
6
7
8
9
10
11
12
CALL.
13
14
15
16
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18
19
CALL.
20
21
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25
26
CALL
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30
      CALL
               

Farm House in Menemsha with North Shore Views!


"Sweeping Views from this Menemsha Farm House!"

Style, warmth, and comfort define this delightful farm house in Menemsha with a water view to the Vineyard Sound. The property is spacious and private. Features include a newly constructed private pool. The house comes with a key to a beach in Aquinnah on Moshup trail and a shared key to Quansoo ...Read the full description.

JUNE 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$8,400.
7
8
9
10
11
12
13
$8,400.
14
15
16
17
18
19
20
$8,400.
21
22
23
24
25
26
27
$10,000.
28
29
30
        $10,000.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$10,000.
5
6
7
8
9
10
11
$10,000.
12
13
14
15
16
17
18
$10,000.
19
20
21
22
23
24
25
$10,000.
26
27
28
29
30
31
  $11,000.
               
AUGUST 2026
S M T W T F S Cost
           
1
$11,000.
2
3
4
5
6
7
8
$11,900.
9
10
11
12
13
14
15
$11,900.
16
17
18
19
20
21
22
$11,900.
23
24
25
26
27
28
29
$11,900.
30
31
          $11,900.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$11,900.
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
$8,500.
27
28
29
30
      $8,500.
               

Private Menemsha Rental Close To Harbor, Town And Beach!


"Great Location, Mile to Menemsha Beach And Watch The Sunset!"

Located on Flanders Lane, this house sits up the hill and looks toward Menemsha. There is a window a/c unit in the upstairs bedroom and another one in a downstairs bedroom. Two of the bedrooms on the lower level have ensuite half bathrooms. The large primary bedroom on the second floor has an ensui...Read the full description.

JUNE 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$3,000.
7
8
9
10
11
12
13
$3,000.
14
15
16
17
18
19
20
$3,000.
21
22
23
24
25
26
27
$3,000.
28
29
30
        $3,800.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$3,800.
5
6
7
8
9
10
11
$3,500.
12
13
14
15
16
17
18
$3,500.
19
20
21
22
23
24
25
$3,500.
26
27
28
29
30
31
  $3,800.
               
AUGUST 2026
S M T W T F S Cost
           
1
$3,800.
2
3
4
5
6
7
8
$3,800.
9
10
11
12
13
14
15
$3,800.
16
17
18
19
20
21
22
$3,800.
23
24
25
26
27
28
29
$3,800.
30
31
          $3,000.
SEPTEMBER 2026
S M T W T F S Cost
   
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
      $3,000.
               

Contemporary Waterfront in Squibnocket!


"Features Waterfront Panoramic Views, Well Equipped Kitchen, 5 Ensuite Bedrooms, & 6 Person Jacuzzi!"

Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches,and high speed internet wifi.

JUNE 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$35,000.
7
8
9
10
11
12
13
$35,000.
14
15
16
17
18
19
20
$35,000.
21
22
23
24
25
26
27
$35,000.
28
29
30
        $40,000.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$40,000.
5
6
7
8
9
10
11
$40,000.
12
13
14
15
16
17
18
$40,000.
19
20
21
22
23
24
25
$40,000.
26
27
28
29
30
31
  $45,000.
               
AUGUST 2026
S M T W T F S Cost
           
1
$45,000.
2
3
4
5
6
7
8
$45,000.
9
10
11
12
13
14
15
$45,000.
16
17
18
19
20
21
22
$45,000.
23
24
25
26
27
28
29
$45,000.
30
31
          $45,000.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$45,000.
6
7
8
9
10
11
12
$30,000.
13
14
15
16
17
18
19
$30,000.
20
21
22
23
24
25
26
$30,000.
27
28
29
30
      $30,000.