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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








Panoramic Chilmark Waterviews With Private Association Beach!


"Unbeatable South Shore Views, Pond Access, Zack's Cliffs Beach Pass, Lucy Vincent And Squibnocket!"

Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$7,500.
8
9
10
11
12
13
14
$7,500.
15
16
17
18
19
20
21
$7,500.
22
23
24
25
26
27
28
$9,000.
29
30
          11,000.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$11,000.
6
7
8
9
10
11
12
$11,000.
13
14
15
16
17
18
19
$11,000.
20
21
22
23
24
25
26
$11,000.
27
28
29
30
31
    $12,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$12,000.
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
$12,000.
24
25
26
27
28
29
30
$12,000.
31
            $12,000.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$12,000.
7
8
9
10
11
12
13
$10,000.
14
15
16
17
18
19
20
$7,500.
21
22
23
24
25
26
27
$7,500.
28
29
30
        $7,500.
               

Chilmark House and Guest House With Atlantic Ocean Views!


"Gracious Vineyard Home with Sweeping Views of Keith Farm land and Atlantic Ocean."

This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four bedrooms, and guest house, with t...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$7,000.
8
9
10
11
12
13
14
$7,000.
15
16
17
18
19
20
21
$7,000.
22
23
24
25
26
27
28
$9,500.
29
30
          $12,000.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$12,000.
6
7
8
9
10
11
12
$12,000.
13
14
15
16
17
18
19
$12,000.
20
21
22
23
24
25
26
$12,000.
27
28
29
30
31
    $12,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$12,000.
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
$12,000.
24
25
26
27
28
29
30
$12,000.
31
            $9,000.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$9,000.
7
8
9
10
11
12
13
$8,000.
14
15
16
17
18
19
20
$8,000.
21
22
23
24
25
26
27
$8,000.
28
29
30
        $8,000.
               

Exceptional Menemsha Views


"Classic Vineyard charm and stellar sunsets."

This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
Call
8
9
10
11
12
13
14
Call
15
16
17
18
19
20
21
Call
22
23
24
25
26
27
28
Call
29
30
          $4,350.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$4,350.
6
7
8
9
10
11
12
$4,350.
13
14
15
16
17
18
19
$4,350.
20
21
22
23
24
25
26
$4,350.
27
28
29
30
31
    $5,250.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$5,250.
3
4
5
6
7
8
9
$5,250.
10
11
12
13
14
15
16
$5,250.
17
18
19
20
21
22
23
$5,250.
24
25
26
27
28
29
30
$5,250.
31
            $5,250.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$5,250.
7
8
9
10
11
12
13
Call
14
15
16
17
18
19
20
Call
21
22
23
24
25
26
27
Call
28
29
30
        Call
               

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 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$10,000.
8
9
10
11
12
13
14
$10,000.
15
16
17
18
19
20
21
$10,000.
22
23
24
25
26
27
28
$10,000.
29
30
          $12,000.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$12,000.
6
7
8
9
10
11
12
$12,000.
13
14
15
16
17
18
19
$12,000.
20
21
22
23
24
25
26
$12,000.
27
28
29
30
31
    $12,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$12,000.
3
4
5
6
7
8
9
$18,000.
10
11
12
13
14
15
16
$18,000.
17
18
19
20
21
22
23
$18,000.
24
25
26
27
28
29
30
$12,000.
31
            $12,000.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$12,000.
7
8
9
10
11
12
13
$10,000.
14
15
16
17
18
19
20
$10,000.
21
22
23
24
25
26
27
$10,000.
28
29
30
        $10,000.