Karen M. Overtoom Logo
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








Impeccable Chilmark Home


"Beautiful Outdoor Spaces"

This remarkable single story home features a large living and dining room with post and beam cathedral ceilings. Floor to ceiling glass doors open onto the outdoor deck overlooking the gorgeous rolling meadows and trees. At the center of the home is the beautiful kitchen with ample work space for ...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$6,200.
8
9
10
11
12
13
14
$6,200.
15
16
17
18
19
20
21
$6,200.
22
23
24
25
26
27
28
$6,200.
29
30
          $6,200.
               
JULY 2025
S M T W T F S Cost
   
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
$6,200.
27
28
29
30
31
    $6,200.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$6,200.
3
4
5
6
7
8
9
$6,200.
10
11
12
13
14
15
16
$6,200.
17
18
19
20
21
22
23
$6,200.
24
25
26
27
28
29
30
$6,200.
31
            $6,200.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$6,200.
7
8
9
10
11
12
13
$6,200.
14
15
16
17
18
19
20
$6,200.
21
22
23
24
25
26
27
$6,200.
28
29
30
        $6,200.
               

Storybook Cottage in Chilmark


"Adorable one bedroom cottage that is beautifully decorated!!!"

Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a fully equipped kitchen, an...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$2,625.
8
9
10
11
12
13
14
$2,625.
15
16
17
18
19
20
21
$2,625.
22
23
24
25
26
27
28
$2,625.
29
30
          $2,625.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$2,625.
6
7
8
9
10
11
12
$2,625.
13
14
15
16
17
18
19
$2,625.
20
21
22
23
24
25
26
$2,625.
27
28
29
30
31
    $2,625.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$2,625.
3
4
5
6
7
8
9
$2,625.
10
11
12
13
14
15
16
$2,625.
17
18
19
20
21
22
23
$2,625.
24
25
26
27
28
29
30
$2,625.
31
            $2,625.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$2,100.
7
8
9
10
11
12
13
$2,100.
14
15
16
17
18
19
20
$2,100.
21
22
23
24
25
26
27
$2,100.
28
29
30
        $2,100.
               

Charming Chilmark Rental Near West Tisbury Center!


"Classic Vineyard Cottage Retreat With Access To Lucy Vincent Beach!"

This bright and cheerful, wooded retreat is truly tranquil, yet just a little over a mile from West Tisbury village where you have Alley's General Store, 7A Foods featuring take-out breakfast and lunch, the gas station, the West Tisbury library, the old Ag Hall where they have the Farmer's Market, A...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$3,675.
8
9
10
11
12
13
14
$3,675.
15
16
17
18
19
20
21
$3,675.
22
23
24
25
26
27
28
$3,675.
29
30
          $3,775.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$3,775.
6
7
8
9
10
11
12
$3,775.
13
14
15
16
17
18
19
$3,775.
20
21
22
23
24
25
26
$3,775.
27
28
29
30
31
    $3,925.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$3,925.
3
4
5
6
7
8
9
$3,925.
10
11
12
13
14
15
16
$3,925.
17
18
19
20
21
22
23
$3,925.
24
25
26
27
28
29
30
$3,925.
31
            $3,925.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$3,925.
7
8
9
10
11
12
13
$3,775.
14
15
16
17
18
19
20
$3,775.
21
22
23
24
25
26
27
$3,775.
28
29
30
        $3,775.
               

Perfect Summer Retreat!


"Beautiful Meadow & Peak of Water View From Middle Road!"

Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four bedroom, 2 bath home has an expans...Read the full description.

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