Your connection to all Martha's Vineyard Real Estate and Vacation Rentals
508-693-7832
508-693-7832


Martha's Vineyard Vacation Rentals in Chilmark








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 2023
S M T W T F S Cost
       
1
2
3
$2,625.
4
5
6
7
8
9
10
$2,625.
11
12
13
14
15
16
17
$2,625.
18
19
20
21
22
23
24
$2,625.
25
26
27
28
29
30
  $2,625.
               
JULY 2023
S M T W T F S Cost
           
1
$2,625.
2
3
4
5
6
7
8
$2,625.
9
10
11
12
13
14
15
$2,625.
16
17
18
19
20
21
22
$2,625.
23
24
25
26
27
28
29
$2,625.
30
31
          $2,625.
AUGUST 2023
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.
               
SEPTEMBER 2023
S M T W T F S Cost
         
1
2
$2,100.
3
4
5
6
7
8
9
$2,100.
10
11
12
13
14
15
16
$2,100.
17
18
19
20
21
22
23
$2,100.
24
25
26
27
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 2023
S M T W T F S Cost
       
1
2
3
$5,000.
4
5
6
7
8
9
10
$5,000.
11
12
13
14
15
16
17
$5,000.
18
19
20
21
22
23
24
$5,000.
25
26
27
28
29
30
  $5,000.
               
JULY 2023
S M T W T F S Cost
           
1
$7,500.
2
3
4
5
6
7
8
$7,500.
9
10
11
12
13
14
15
$7,500.
16
17
18
19
20
21
22
$7,500.
23
24
25
26
27
28
29
$7,500.
30
31
          $7,500.
AUGUST 2023
S M T W T F S Cost
   
1
2
3
4
5
$8,500.
6
7
8
9
10
11
12
$8,500.
13
14
15
16
17
18
19
$8,500.
20
21
22
23
24
25
26
$8,500.
27
28
29
30
31
    $8,500.
               
SEPTEMBER 2023
S M T W T F S Cost
         
1
2
$5,000.
3
4
5
6
7
8
9
$5,000.
10
11
12
13
14
15
16
$5,000.
17
18
19
20
21
22
23
$5,000.
24
25
26
27
28
29
30
$5,000.
               

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 2023
S M T W T F S Cost
       
1
2
3
$3,000.
4
5
6
7
8
9
10
$3,000.
11
12
13
14
15
16
17
$3,000.
18
19
20
21
22
23
24
$3,000.
25
26
27
28
29
30
  $3,425.
               
JULY 2023
S M T W T F S Cost
           
1
$3,425.
2
3
4
5
6
7
8
$3,425.
9
10
11
12
13
14
15
$3,425.
16
17
18
19
20
21
22
$3,425.
23
24
25
26
27
28
29
$3,425.
30
31
          $3,625.
AUGUST 2023
S M T W T F S Cost
   
1
2
3
4
5
$3,625.
6
7
8
9
10
11
12
$3,625.
13
14
15
16
17
18
19
$3,625.
20
21
22
23
24
25
26
$3,625.
27
28
29
30
31
    $3,625.
               
SEPTEMBER 2023
S M T W T F S Cost
         
1
2
$3,625.
3
4
5
6
7
8
9
$3,325.
10
11
12
13
14
15
16
$3,325.
17
18
19
20
21
22
23
$2,825.
24
25
26
27
28
29
30
$2,825.
               

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 2023
S M T W T F S Cost
       
1
2
3
Call
4
5
6
7
8
9
10
Call
11
12
13
14
15
16
17
Call
18
19
20
21
22
23
24
Call
25
26
27
28
29
30
  Call
               
JULY 2023
S M T W T F S Cost
           
1
$5,500.
2
3
4
5
6
7
8
$5,500.
9
10
11
12
13
14
15
$5,500.
16
17
18
19
20
21
22
$5,500.
23
24
25
26
27
28
29
$5,500.
30
31
          $6,000.
AUGUST 2023
S M T W T F S Cost
   
1
2
3
4
5
$6,000.
6
7
8
9
10
11
12
$6,000.
13
14
15
16
17
18
19
$6,000.
20
21
22
23
24
25
26
$6,000.
27
28
29
30
31
    $6,000.
               
SEPTEMBER 2023
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
               

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 2023
S M T W T F S Cost
       
1
2
3
Call
4
5
6
7
8
9
10
Call
11
12
13
14
15
16
17
Call
18
19
20
21
22
23
24
Call
25
26
27
28
29
30
  Call
               
JULY 2023
S M T W T F S Cost
           
1
Call
2
3
4
5
6
7
8
Call
9
10
11
12
13
14
15
Call
16
17
18
19
20
21
22
Call
23
24
25
26
27
28
29
Call
30
31
          Call
AUGUST 2023
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
    $10,000.
               
SEPTEMBER 2023
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
Call
17
18
19
20
21
22
23
Call
24
25
26
27
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 2023
S M T W T F S Cost
       
1
2
3
$5,000.
4
5
6
7
8
9
10
$5,000.
11
12
13
14
15
16
17
$5,000.
18
19
20
21
22
23
24
$5,000.
25
26
27
28
29
30
  $5,500.
               
JULY 2023
S M T W T F S Cost
           
1
$5,500.
2
3
4
5
6
7
8
$5,500.
9
10
11
12
13
14
15
$5,500.
16
17
18
19
20
21
22
$5,500.
23
24
25
26
27
28
29
$5,500.
30
31
          $6,000.
AUGUST 2023
S M T W T F S Cost
   
1
2
3
4
5
$6,000.
6
7
8
9
10
11
12
$6,000.
13
14
15
16
17
18
19
$6,000.
20
21
22
23
24
25
26
$6,000.
27
28
29
30
31
    $6,000.
               
SEPTEMBER 2023
S M T W T F S Cost
         
1
2
$6,000.
3
4
5
6
7
8
9
$5,000.
10
11
12
13
14
15
16
$5,000.
17
18
19
20
21
22
23
$5,000.
24
25
26
27
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 2023
S M T W T F S Cost
       
1
2
3
Call
4
5
6
7
8
9
10
Call
11
12
13
14
15
16
17
Call
18
19
20
21
22
23
24
$15,000.
25
26
27
28
29
30
  $16,000.
               
JULY 2023
S M T W T F S Cost
           
1
$16,000.
2
3
4
5
6
7
8
$16,000.
9
10
11
12
13
14
15
$16,000.
16
17
18
19
20
21
22
$16,000.
23
24
25
26
27
28
29
$16,000.
30
31
          $16,000.
AUGUST 2023
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.
               
SEPTEMBER 2023
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
$14,000.
17
18
19
20
21
22
23
Call
24
25
26
27
28
29
30
Call
               

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 2023
S M T W T F S Cost
       
1
2
3
Call
4
5
6
7
8
9
10
Call
11
12
13
14
15
16
17
Call
18
19
20
21
22
23
24
Call
25
26
27
28
29
30
  $8,000.
               
JULY 2023
S M T W T F S Cost
           
1
$8,000.
2
3
4
5
6
7
8
$8,000..
9
10
11
12
13
14
15
$8,000.
16
17
18
19
20
21
22
$8,000.
23
24
25
26
27
28
29
$8,000..
30
31
          $9,000.
AUGUST 2023
S M T W T F S Cost
   
1
2
3
4
5
$9,000.
6
7
8
9
10
11
12
$9,000.
13
14
15
16
17
18
19
$9,000.
20
21
22
23
24
25
26
$9,900.
27
28
29
30
31
    $9,900.
               
SEPTEMBER 2023
S M T W T F S Cost
         
1
2
$9,000.
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
               

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 2023
S M T W T F S Cost
       
1
2
3
$3,000.
4
5
6
7
8
9
10
$3,000.
11
12
13
14
15
16
17
$3,000.
18
19
20
21
22
23
24
$3,000.
25
26
27
28
29
30
  $3,000.
               
JULY 2023
S M T W T F S Cost
           
1
$3,000.
2
3
4
5
6
7
8
$4,000.
9
10
11
12
13
14
15
$4,000.
16
17
18
19
20
21
22
$4,000.
23
24
25
26
27
28
29
$4,000.
30
31
          $4,200.
AUGUST 2023
S M T W T F S Cost
   
1
2
3
4
5
$4,200.
6
7
8
9
10
11
12
$4,200.
13
14
15
16
17
18
19
$4,200.
20
21
22
23
24
25
26
$4,200.
27
28
29
30
31
    $4,200.
               
SEPTEMBER 2023
S M T W T F S Cost
         
1
2
$4,200.
3
4
5
6
7
8
9
$3,500.
10
11
12
13
14
15
16
$2,800.
17
18
19
20
21
22
23
$2,800.
24
25
26
27
28
29
30
$2,800.
               

Panoramic Chilmark Waterviews With Private Association Beach!


"Unbeatable South Shore Views, Pond Access, Zack's Cliffs Beach Pass, Lucy Vincent And Squibnocket!"

Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all...Read the full description.

JUNE 2023
S M T W T F S Cost
       
1
2
3
$7,500.
4
5
6
7
8
9
10
$7,500.
11
12
13
14
15
16
17
$7,500.
18
19
20
21
22
23
24
$7,500.
25
26
27
28
29
30
  $9,000.
               
JULY 2023
S M T W T F S Cost
           
1
$9,000.
2
3
4
5
6
7
8
$11,000.
9
10
11
12
13
14
15
$11,000.
16
17
18
19
20
21
22
$11,000.
23
24
25
26
27
28
29
$11,000.
30
31
          $12,000.
AUGUST 2023
S M T W T F S Cost
   
1
2
3
4
5
$12,000.
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
    $12,000.
               
SEPTEMBER 2023
S M T W T F S Cost
         
1
2
$12,000.
3
4
5
6
7
8
9
$10,000.
10
11
12
13
14
15
16
$7,500.
17
18
19
20
21
22
23
$7,500.
24
25
26
27
28
29
30
$7,500.
               

Chilmark House and Guest House With Atlantic Ocean Views!


"Gracious Vineyard Home with Sweeping Views of Keith Farm land and Atlantic Ocean."

This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four bedrooms, and guest house, with t...Read the full description.

JUNE 2023
S M T W T F S Cost
       
1
2
3
$7,000.
4
5
6
7
8
9
10
$7,000.
11
12
13
14
15
16
17
$7,000.
18
19
20
21
22
23
24
$7,000.
25
26
27
28
29
30
  $9,500.
               
JULY 2023
S M T W T F S Cost
           
1
$9,500.
2
3
4
5
6
7
8
$9,500.
9
10
11
12
13
14
15
$9,500.
16
17
18
19
20
21
22
$9,500.
23
24
25
26
27
28
29
$9,500.
30
31
          $10,000.
AUGUST 2023
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
$9,500.
20
21
22
23
24
25
26
$9,000.
27
28
29
30
31
    $9,000.
               
SEPTEMBER 2023
S M T W T F S Cost
         
1
2
$9,000.
3
4
5
6
7
8
9
$8,000.
10
11
12
13
14
15
16
$8,000.
17
18
19
20
21
22
23
$8,000.
24
25
26
27
28
29
30
$8,000.
               

Exceptional Menemsha Views


"Classic Vineyard charm and stellar sunsets."

This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

JUNE 2023
S M T W T F S Cost
       
1
2
3
CALL
4
5
6
7
8
9
10
CALL
11
12
13
14
15
16
17
CALL
18
19
20
21
22
23
24
CALL
25
26
27
28
29
30
  CALL
               
JULY 2023
S M T W T F S Cost
           
1
CALL
2
3
4
5
6
7
8
$3700.
9
10
11
12
13
14
15
$3700.
16
17
18
19
20
21
22
$3700.
23
24
25
26
27
28
29
$3700.
30
31
          $4500.