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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








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.
               

Menemsha Waterview Rental


"Brand New Contemporary Chilmark Waterview Home!"

Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from reclaimed red birch, practic...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
Call
3
4
5
6
7
8
9
Call
10
11
12
13
14
15
16
Call
17
18
19
20
21
22
23
Call
24
25
26
27
28
29
30
Call
31
            Call
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
               

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.