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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








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 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$8,400.
8
9
10
11
12
13
14
$8,400.
15
16
17
18
19
20
21
$8,400.
22
23
24
25
26
27
28
$10,000.
29
30
          $10,000.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$10,000.
6
7
8
9
10
11
12
$10,000.
13
14
15
16
17
18
19
$10,000.
20
21
22
23
24
25
26
$10,000.
27
28
29
30
31
    $11,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$11,000.
3
4
5
6
7
8
9
$11,900.
10
11
12
13
14
15
16
$11,900.
17
18
19
20
21
22
23
$11,900.
24
25
26
27
28
29
30
$11,900.
31
            $11,900.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$8,500.
7
8
9
10
11
12
13
$8,500.
14
15
16
17
18
19
20
$8,500.
21
22
23
24
25
26
27
$8,500.
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 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$3,000.
8
9
10
11
12
13
14
$3,000.
15
16
17
18
19
20
21
$3,000.
22
23
24
25
26
27
28
$3,000.
29
30
          $3,800.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$3,800.
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
31
    $3,500.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$3,500.
3
4
5
6
7
8
9
$3,800.
10
11
12
13
14
15
16
$3,800.
17
18
19
20
21
22
23
$3,800.
24
25
26
27
28
29
30
$3,800.
31
            $3,000.
SEPTEMBER 2025
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
        $3,000.
               

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 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$35,000.
8
9
10
11
12
13
14
$35,000.
15
16
17
18
19
20
21
$35,000.
22
23
24
25
26
27
28
$35,000.
29
30
          $40,000.
               
JULY 2025
S M T W T F S Cost
   
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
    $45,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$45,000.
3
4
5
6
7
8
9
$45,000.
10
11
12
13
14
15
16
$45,000.
17
18
19
20
21
22
23
$45,000.
24
25
26
27
28
29
30
$45,000.
31
            $45,000.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$45,000.
7
8
9
10
11
12
13
$30,000.
14
15
16
17
18
19
20
$30,000.
21
22
23
24
25
26
27
$30,000.
28
29
30
        $30,000.
               

Idyllic Chilmark Home with Spa Pool!!


"Beautiful Chilmark Home"

At the quieter end of the Island, this one-level, 4 bedroom, sun-splashed home holds court atop a hill in Chilmark. Near Menemsha, the charming fishing village that will steal your heart, this gem is one mile from world-class Lucy Vincent Beach and surrounded by a network of wooded hiking trails. En...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$7,350.
8
9
10
11
12
13
14
$7,350.
15
16
17
18
19
20
21
$8,000.
22
23
24
25
26
27
28
$12,400.
29
30
          $13,000.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$13,000.
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
    $13,500.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$13,500.
3
4
5
6
7
8
9
$13,500.
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
$13,000.
31
            $8,300.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$8,300.
7
8
9
10
11
12
13
$7,650.
14
15
16
17
18
19
20
$7,650.
21
22
23
24
25
26
27
$7,650.
28
29
30
        $4,800.