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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!"

This spacious ten room, architectural award winning design home is perched high on a hill with panoramic views of the Vineyard Sound and the Elizabeth Islands. There are five bedrooms, four and one half baths, a large deck for entertaining and watching the breathtaking sunsets, and three outdoor pat...Read the full description.

JUNE 2024
S M T W T F S Cost
           
1
$12,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$12,000
16
17
18
19
20
21
22
$12,000
23
24
25
26
27
28
29
$14,000
30
            $14,000
JULY 2024
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
31
      Call
               
AUGUST 2024
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
31
Call
               
SEPTEMBER 2024
S M T W T F S Cost
1
2
3
4
5
6
7
$14,000
8
9
10
11
12
13
14
$14,000
15
16
17
18
19
20
21
$12,000
22
23
24
25
26
27
28
$12,000
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 2024
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
$8,000.
30
            $8,000.
JULY 2024
S M T W T F S Cost
 
1
2
3
4
5
6
$8,000.
7
8
9
10
11
12
13
$8,000.
14
15
16
17
18
19
20
$8,000.
21
22
23
24
25
26
27
$8,000.
28
29
30
31
      $9,000.
               
AUGUST 2024
S M T W T F S Cost
       
1
2
3
$9,000.
4
5
6
7
8
9
10
$9,000.
11
12
13
14
15
16
17
$9,000.
18
19
20
21
22
23
24
$9,900.
25
26
27
28
29
30
31
$9,900.
               
SEPTEMBER 2024
S M T W T F S Cost
1
2
3
4
5
6
7
$9,000.
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
               

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 2024
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
$9,000.
30
            $11,000.
JULY 2024
S M T W T F S Cost
 
1
2
3
4
5
6
$11,000.
7
8
9
10
11
12
13
$11,000.
14
15
16
17
18
19
20
$11,000.
21
22
23
24
25
26
27
$11,000.
28
29
30
31
      $12,000.
               
AUGUST 2024
S M T W T F S Cost
       
1
2
3
$12,000.
4
5
6
7
8
9
10
$12,000.
11
12
13
14
15
16
17
$12,000.
18
19
20
21
22
23
24
$12,000.
25
26
27
28
29
30
31
$12,000.
               
SEPTEMBER 2024
S M T W T F S Cost
1
2
3
4
5
6
7
$12,000.
8
9
10
11
12
13
14
$10,000.
15
16
17
18
19
20
21
$7,500.
22
23
24
25
26
27
28
$7,500.
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 2024
S M T W T F S Cost
           
1
$7,000.
2
3
4
5
6
7
8
$7,000.
9
10
11
12
13
14
15
$7,000.
16
17
18
19
20
21
22
$7,000.
23
24
25
26
27
28
29
$9,500.
30
            $9,500.
JULY 2024
S M T W T F S Cost
 
1
2
3
4
5
6
$9,500.
7
8
9
10
11
12
13
$9,500.
14
15
16
17
18
19
20
$9,500.
21
22
23
24
25
26
27
$9,500.
28
29
30
31
      $10,000.
               
AUGUST 2024
S M T W T F S Cost
       
1
2
3
$10,000.
4
5
6
7
8
9
10
$10,000.
11
12
13
14
15
16
17
$9,500.
18
19
20
21
22
23
24
$9,000.
25
26
27
28
29
30
31
$9,000.
               
SEPTEMBER 2024
S M T W T F S Cost
1
2
3
4
5
6
7
$9,000.
8
9
10
11
12
13
14
$8,000.
15
16
17
18
19
20
21
$8,000.
22
23
24
25
26
27
28
$8,000.
29
30
          $8,000.
               

Farm House in Menemsha with North Shore Views!


"Sweeping Views from this Menemsha Farm House!"

Style, warmth, and comfort define this delightful farm house in Menemsha with a water view to the Vineyard Sound. The property is spacious and private. Features include a newly constructed private pool. The house comes with a key to a beach in Aquinnah on Moshup trail and a shared key to Quansoo...Read the full description.

JUNE 2024
S M T W T F S Cost
           
1
$8,400.
2
3
4
5
6
7
8
$8,400.
9
10
11
12
13
14
15
$8,400.
16
17
18
19
20
21
22
$8,400.
23
24
25
26
27
28
29
$10,000.
30
            $10,000.
JULY 2024
S M T W T F S Cost
 
1
2
3
4
5
6
$10,000.
7
8
9
10
11
12
13
$10,000.
14
15
16
17
18
19
20
$10,000.
21
22
23
24
25
26
27
$10,000.
28
29
30
31
      $11,000.
               
AUGUST 2024
S M T W T F S Cost
       
1
2
3
$11,000.
4
5
6
7
8
9
10
$11,900.
11
12
13
14
15
16
17
$11,900.
18
19
20
21
22
23
24
$11,900.
25
26
27
28
29
30
31
$11,900.
               
SEPTEMBER 2024
S M T W T F S Cost
1
2
3
4
5
6
7
$8,500.
8
9
10
11
12
13
14
$8,500.
15
16
17
18
19
20
21
$8,500.
22
23
24
25
26
27
28
$8,500.
29
30
          $8,500.
               

Private Menemsha Rental Close To Harbor, Town And Beach!


"Great Location, Mile to Menemsha Beach And Watch The Sunset!"

Located on Flanders Lane, this house sits up the hill and looks toward Menemsha. There is a window a/c unit in the upstairs bedroom and another one in a downstairs bedroom. Two of the bedrooms on the lower level have ensuite half bathrooms. The large primary bedroom on the second floor has an ensui...Read the full description.

JUNE 2024
S M T W T F S Cost
           
1
$3,000.
2
3
4
5
6
7
8
$3,000.
9
10
11
12
13
14
15
$3,000.
16
17
18
19
20
21
22
$3,000.
23
24
25
26
27
28
29
$3,000.
30
            $3,800.
JULY 2024
S M T W T F S Cost
 
1
2
3
4
5
6
$3,800.
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
31
      $3,500.
               
AUGUST 2024
S M T W T F S Cost
       
1
2
3
$3,500.
4
5
6
7
8
9
10
$3,800.
11
12
13
14
15
16
17
$3,800.
18
19
20
21
22
23
24
$3,800.
25
26
27
28
29
30
31
$3,800.
               
SEPTEMBER 2024
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
          $3,000.
               

Contemporary Waterfront in Squibnocket!


"Features Waterfront Panoramic Views, Well Equipped Kitchen, 5 Ensuite Bedrooms, & 6 Person Jacuzzi!"

Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches,and high speed internet wifi.

JUNE 2024
S M T W T F S Cost
           
1
$35,000.
2
3
4
5
6
7
8
$35,000.
9
10
11
12
13
14
15
$35,000.
16
17
18
19
20
21
22
$35,000.
23
24
25
26
27
28
29
$35,000.
30
            $40,000.
JULY 2024
S M T W T F S Cost
 
1
2
3
4
5
6
$40,000.
7
8
9
10
11
12
13
$40,000.
14
15
16
17
18
19
20
$40,000.
21
22
23
24
25
26
27
$40,000.
28
29
30
31
      $45,000.
               
AUGUST 2024
S M T W T F S Cost
       
1
2
3
$45,000.
4
5
6
7
8
9
10
$45,000.
11
12
13
14
15
16
17
$45,000.
18
19
20
21
22
23
24
$45,000.
25
26
27
28
29
30
31
$45,000.
               
SEPTEMBER 2024
S M T W T F S Cost
1
2
3
4
5
6
7
$45,000
8
9
10
11
12
13
14
$30,000
15
16
17
18
19
20
21
$30,000
22
23
24
25
26
27
28
$30,000
29
30
          $30,000
               

Idyllic Chilmark Home with Spa Pool!!


"NEWLY DISCOUNTED PRICING FOR SUMMER 2024!"

At the quieter end of the Island, this one-level, 4 bedroom, sun-splashed home holds court atop a hill in Chilmark. Near Menemsha, the charming fishing village that will steal your heart, this gem is one mile from world-class Lucy Vincent Beach and surrounded by a network of wooded hiking trails. En...Read the full description.

JUNE 2024
S M T W T F S Cost
           
1
$4,875.
2
3
4
5
6
7
8
$4,875.
9
10
11
12
13
14
15
$4,875.
16
17
18
19
20
21
22
$4,875.
23
24
25
26
27
28
29
$4,875.
30
            $7,800.
JULY 2024
S M T W T F S Cost
 
1
2
3
4
5
6
$7,800.
7
8
9
10
11
12
13
$6,825.
14
15
16
17
18
19
20
$8,000.
21
22
23
24
25
26
27
$8,000.
28
29
30
31
      $13,500.
               
AUGUST 2024
S M T W T F S Cost
       
1
2
3
$7,875.
4
5
6
7
8
9
10
$7,875.
11
12
13
14
15
16
17
$13,500.
18
19
20
21
22
23
24
$13,500.
25
26
27
28
29
30
31
$13,500.
               
SEPTEMBER 2024
S M T W T F S Cost
1
2
3
4
5
6
7
$8,300.
8
9
10
11
12
13
14
$7,650.
15
16
17
18
19
20
21
$5,600.
22
23
24
25
26
27
28
$5,600.
29
30
          $5,600.
               

Sophisticated Country Charmer with Central Air


"Chilmark Summer Rental Across From Great Rock Bight Beach!"

A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine floori...Read the full description.

JUNE 2024
S M T W T F S Cost
           
1
$2,800.
2
3
4
5
6
7
8
$2,800.
9
10
11
12
13
14
15
$2,800.
16
17
18
19
20
21
22
$3,300.
23
24
25
26
27
28
29
$3,300..
30
            $3,300.
JULY 2024
S M T W T F S Cost
 
1
2
3
4
5
6
$3,300.
7
8
9
10
11
12
13
$3,300.
14
15
16
17
18
19
20
$3,700.
21
22
23
24
25
26
27
$3,700.
28
29
30
31
      $3,700.
               
AUGUST 2024
S M T W T F S Cost
       
1
2
3
$3,700.
4
5
6
7
8
9
10
$3,700.
11
12
13
14
15
16
17
$3,700.
18
19
20
21
22
23
24
$3,700.
25
26
27
28
29
30
31
$3,700.
               
SEPTEMBER 2024
S M T W T F S Cost
1
2
3
4
5
6
7
$3,300.
8
9
10
11
12
13
14
$3,300.
15
16
17
18
19
20
21
$3,300.
22
23
24
25
26
27
28
$2,800.
29
30
          CALL
               

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 2024
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
            $2,625.
JULY 2024
S M T W T F S Cost
 
1
2
3
4
5
6
$2,625.
7
8
9
10
11
12
13
$2,625.
14
15
16
17
18
19
20
$2,625.
21
22
23
24
25
26
27
$2,625.
28
29
30
31
      $2,625.
               
AUGUST 2024
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
31
$2,625.
               
SEPTEMBER 2024
S M T W T F S Cost
1
2
3
4
5
6
7
$2,100.
8
9
10
11
12
13
14
$2,100.
15
16
17
18
19
20
21
$2,100.
22
23
24
25
26
27
28
$2,100.
29
30
          $2,100.
               

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 2024
S M T W T F S Cost
           
1
$4,000.
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
            $4,500.
JULY 2024
S M T W T F S Cost
 
1
2
3
4
5
6
$4,500.
7
8
9
10
11
12
13
$4,500.
14
15
16
17
18
19
20
$4,500.
21
22
23
24
25
26
27
$5,500.
28
29
30
31
      $6,000.
               
AUGUST 2024
S M T W T F S Cost
       
1
2
3
$6,000.
4
5
6
7
8
9
10
$6,000.
11
12
13
14
15
16
17
$6,000.
18
19
20
21
22
23
24
$6,000.
25
26
27
28
29
30
31
$6,000.
               
SEPTEMBER 2024
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
          $4,000.
               

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 2024
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JULY 2024
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