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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








Wonderful Chilmark Retreat


"Centrally Located off Middle Road"

Come experience the rest and relaxation of slowing down in this adorable well appointed and air conditioned family home in the heart of Chilmark surrounded by rolling fields and beautiful stone walls. Tucked back off Middle Road, this four bedroom two bath rental comes with linens and towels, high ...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$3,500.
8
9
10
11
12
13
14
$3,500.
15
16
17
18
19
20
21
$3,500.
22
23
24
25
26
27
28
$3,500.
29
30
          $4,700.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$4,700.
6
7
8
9
10
11
12
$4,700.
13
14
15
16
17
18
19
$4,700.
20
21
22
23
24
25
26
$4,700.
27
28
29
30
31
    $4,700.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$4,700.
3
4
5
6
7
8
9
$5,600.
10
11
12
13
14
15
16
$5,600.
17
18
19
20
21
22
23
$5,600.
24
25
26
27
28
29
30
$5,600.
31
            $4,700.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$4,700.
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
$3,500.
28
29
30
        $3,500.
               

Lovely Private Home on Harlock's Pond


"Chilmark Estate with Private Beach and Water View"

Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely...Read the full description.

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

Gorgeous Remodeled High End Chilmark Home


"Bright, Crisp Home In The Heart Of Chilmark!"

Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass ...Read the full description.

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

Chilmark Estate with Waterviews


"Association Tennis and Beach"

Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as...Read the full description.

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