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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 Aquinnah







Picturesque Water View Home

"Gorgeous Atlantic Views!"

Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoo...Read the full description.

JUNE 2026
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
$4,500.
28
29
30
        $5,500.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$5,500.
5
6
7
8
9
10
11
$5,500.
12
13
14
15
16
17
18
$5,500.
19
20
21
22
23
24
25
$5,500.
26
27
28
29
30
31
  $6,000.
               
AUGUST 2026
S M T W T F S Cost
           
1
$6,000.
2
3
4
5
6
7
8
$6,000.
9
10
11
12
13
14
15
$6,000.
16
17
18
19
20
21
22
$5,500.
23
24
25
26
27
28
29
$5,500.
30
31
          $4,500.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$4,500.
6
7
8
9
10
11
12
$4,500.
13
14
15
16
17
18
19
Call
20
21
22
23
24
25
26
Call
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28
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30
      Call
               

Aquinnah Waterview Rental

"Fabulous waterviews from this privately located, 3 bedroom contemporary."

Uniquely designed, 3-bedroom, 2 full bath contemporary home, divided between three floors and set upon an acre of lush grounds with waterviews overlooking Vineyard Sound and the Elizabeth Islands. Privacy enhanced with large tracts of conservation land nearby and walking distance to Lobsterville Bea...Read the full description.

JUNE 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$2,800.
7
8
9
10
11
12
13
$2,800.
14
15
16
17
18
19
20
$2,800.
21
22
23
24
25
26
27
$2,800.
28
29
30
        $3,500.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$3,500.
5
6
7
8
9
10
11
$3,500.
12
13
14
15
16
17
18
$3,500.
19
20
21
22
23
24
25
$3,500.
26
27
28
29
30
31
  $3,800.
               
AUGUST 2026
S M T W T F S Cost
           
1
$3,800.
2
3
4
5
6
7
8
$3,800.
9
10
11
12
13
14
15
$3,800.
16
17
18
19
20
21
22
$3,800.
23
24
25
26
27
28
29
$3,800.
30
31
          $3,800.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$3,800.
6
7
8
9
10
11
12
$2,800.
13
14
15
16
17
18
19
$2,800.
20
21
22
23
24
25
26
$2,800.
27
28
29
30
      $2,800.
               

The Sea Owl House

"Sophistication Near the Sea"

Newly built custom post and beam home with bright open concept living, dining and kitchen. Bright and light filled home with high ceilings, wood floors, and soothing neutral tones make this the perfect place to gather with family and friends for a fun and relaxing vacation. Enjoy a peak of the wate...Read the full description.

JUNE 2026
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
        $12,000.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$12,000.
5
6
7
8
9
10
11
$10,000.
12
13
14
15
16
17
18
$10,000.
19
20
21
22
23
24
25
$10,000.
26
27
28
29
30
31
  $10,000.
               
AUGUST 2026
S M T W T F S Cost
           
1
$10,000.
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
$12,000.
30
31
          $12,000.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$12,000.
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
      Call
               

Charming Aquinnah Cottage

"Classic Vineyard cottage with access to Philbin and Lobsterville Beaches"

Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to town beaches. Philbin and Moshup Trail Beach passes bought separately. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze...Read the full description.

JUNE 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$2,500.
7
8
9
10
11
12
13
$2,500.
14
15
16
17
18
19
20
$2,500.
21
22
23
24
25
26
27
$2,500.
28
29
30
        $2,900.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$2,900.
5
6
7
8
9
10
11
$2,900.
12
13
14
15
16
17
18
$2,900.
19
20
21
22
23
24
25
$2,900.
26
27
28
29
30
31
  $3,200.
               
AUGUST 2026
S M T W T F S Cost
           
1
$3,200.
2
3
4
5
6
7
8
$3,300.
9
10
11
12
13
14
15
$3,400.
16
17
18
19
20
21
22
$3,000.
23
24
25
26
27
28
29
$3,000.
30
31
          $3,000.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$3,000.
6
7
8
9
10
11
12
$2,900.
13
14
15
16
17
18
19
$2,500.
20
21
22
23
24
25
26
$2,500.
27
28
29
30
      $2,500.