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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








Chilmark Waterview Rental With Beach & Tennis!


"Beautiful Spring Point Contemporary Home With Panoramic View Of The Vineyard Sound!"

Gracefully situated atop the hills of Spring Point in Chilmark, the 4-BR (sleeps 8-10) home features panoramic water views sweeping from Gay Head Light to the Elisabeth Islands and east. This 4.750 sf family sanctuary was designed to balance inside and outside family gathering spots with private sp...Read the full description.

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

Chilmark Waterview With Beach And Tennis!


"Fabulous Spring Point Home With Breathtaking Waterviews, Private Association Beach & Tennis!"

Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half bath, a master suite with pr...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
$8,000.
29
30
          $8,000.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$8,000.
6
7
8
9
10
11
12
$8,000.
13
14
15
16
17
18
19
$8,000.
20
21
22
23
24
25
26
$8,000.
27
28
29
30
31
    $9,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$9,000.
3
4
5
6
7
8
9
$9,000.
10
11
12
13
14
15
16
$9,000.
17
18
19
20
21
22
23
$9,900.
24
25
26
27
28
29
30
$9,900.
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
Call
14
15
16
17
18
19
20
Call
21
22
23
24
25
26
27
Call
28
29
30
        Call
               

Wonderful open spacious home in Chilmark


"Open, bright home with Beautiful Gardens"

Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and enjoy the view. Short driv...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
$3,800.
13
14
15
16
17
18
19
$3,800.
20
21
22
23
24
25
26
$4,000.
27
28
29
30
31
    $4,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$4,000.
3
4
5
6
7
8
9
$4,000.
10
11
12
13
14
15
16
$4,000.
17
18
19
20
21
22
23
$4,000.
24
25
26
27
28
29
30
$4,000.
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
$3,500.
14
15
16
17
18
19
20
$2,800.
21
22
23
24
25
26
27
$2,800.
28
29
30
        $2,800.
               

Outstanding Chilmark Guest House


"Cozy and Modern Interior"

Sun splashed Chilmark guest house with post and beam cathedral ceilings throughout. Large living and dining room with glass doors onto the outdoor deck overlooking the peaceful pastoral surroundings. Efficient and sleek kitchen fully equipped for all your culinary needs. One bedroom has a set of ...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$4,700.
8
9
10
11
12
13
14
$4,700.
15
16
17
18
19
20
21
$4,700.
22
23
24
25
26
27
28
$4,700.
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
$4,700.
10
11
12
13
14
15
16
$4,700.
17
18
19
20
21
22
23
$4,700.
24
25
26
27
28
29
30
$4,700.
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
$4,200.
14
15
16
17
18
19
20
$4,200.
21
22
23
24
25
26
27
$4,200.
28
29
30
        $4,200.