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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 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$4,500.
8
9
10
11
12
13
14
$4,500.
15
16
17
18
19
20
21
$4,500.
22
23
24
25
26
27
28
$4,500.
29
30
          $5,500.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$5,500.
6
7
8
9
10
11
12
$5,500.
13
14
15
16
17
18
19
$5,500.
20
21
22
23
24
25
26
$5,000.
27
28
29
30
31
    $6,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$6,000.
3
4
5
6
7
8
9
$6,000.
10
11
12
13
14
15
16
$6,000.
17
18
19
20
21
22
23
$5,500.
24
25
26
27
28
29
30
$5,500.
31
            $4,500.
SEPTEMBER 2025
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
Call
21
22
23
24
25
26
27
Call
28
29
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 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$2,800.
8
9
10
11
12
13
14
$2,800.
15
16
17
18
19
20
21
$2,800.
22
23
24
25
26
27
28
$2,800.
29
30
          $3,500.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$3,500.
6
7
8
9
10
11
12
$3,500.
13
14
15
16
17
18
19
$3,500.
20
21
22
23
24
25
26
$3,500.
27
28
29
30
31
    $3,800.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$3,800.
3
4
5
6
7
8
9
$3,800.
10
11
12
13
14
15
16
$3,800.
17
18
19
20
21
22
23
$3,800.
24
25
26
27
28
29
30
$3,800.
31
            $3,800.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$3,800.
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
        $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 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
          $12,000.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$12,000.
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.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$10,000.
3
4
5
6
7
8
9
$12,000.
10
11
12
13
14
15
16
$12,000.
17
18
19
20
21
22
23
$12,000.
24
25
26
27
28
29
30
$12,000.
31
            $12,000.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$12,000.
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
               

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 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$2,500.
8
9
10
11
12
13
14
$2,500.
15
16
17
18
19
20
21
$2,500.
22
23
24
25
26
27
28
$2,500.
29
30
          $2,900.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$2,900.
6
7
8
9
10
11
12
$2,900.
13
14
15
16
17
18
19
$2,900.
20
21
22
23
24
25
26
$2,900.
27
28
29
30
31
    $3,200.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$3,200.
3
4
5
6
7
8
9
$3,300.
10
11
12
13
14
15
16
$3,400.
17
18
19
20
21
22
23
$3,000.
24
25
26
27
28
29
30
$3,000.
31
            $3,000.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$3,000.
7
8
9
10
11
12
13
$2,900.
14
15
16
17
18
19
20
$2,500.
21
22
23
24
25
26
27
$2,500.
28
29
30
        $2,500.
               

Breathtaking Waterfront Property


"Mesmerizing Views of Menemsha Pond and Ocean"

Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of y...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
$25,000.
6
7
8
9
10
11
12
$25,000.
13
14
15
16
17
18
19
$25,000.
20
21
22
23
24
25
26
$25,000.
27
28
29
30
31
    $25,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$25,000.
3
4
5
6
7
8
9
$25,000.
10
11
12
13
14
15
16
$25,000.
17
18
19
20
21
22
23
$25,000.
24
25
26
27
28
29
30
$25,000.
31
            $25,000.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$25,000.
7
8
9
10
11
12
13
$20,000.
14
15
16
17
18
19
20
$16,000.
21
22
23
24
25
26
27
$16,000.
28
29
30
        $16,000.
               

Private Waterview Home


"Enjoy Philibin Beach, Peaceful Surroundings From This Stunning 5 Bedroom Water View Home"

This beautifully designed and built home is privately sited on 12.23 acres overlooking a pastoral setting with amazing ocean views and bordered by stone walls. The spacious entry hall steps into a formal living and dining room with oversized windows that take in the amazing North Shore ocean views, ...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
N/A
3
4
5
6
7
8
9
$18,000
10
11
12
13
14
15
16
$18,000
17
18
19
20
21
22
23
$18,000
24
25
26
27
28
29
30
$18,000
31
            $18,000
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
               

Aquinnah Cottage Retreat


"Perfect Aquinnah Retreat Close to Philibin Beach"

Peaceful and private, recently updated cottage nestled on over 2 acres of land in Aquinnah. The house is bright and airy with all the amenities you need to feel at home on the Vineyard. The space Sleeping arrangements include a queen bed in the large second floor bedroom, and a comfortable full si...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
2500
8
9
10
11
12
13
14
2500
15
16
17
18
19
20
21
2500
22
23
24
25
26
27
28
2500
29
30
          2500
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
2800
6
7
8
9
10
11
12
2800
13
14
15
16
17
18
19
2800
20
21
22
23
24
25
26
2800
27
28
29
30
31
    2800
               
AUGUST 2025
S M T W T F S Cost
         
1
2
2800
3
4
5
6
7
8
9
2800
10
11
12
13
14
15
16
2800
17
18
19
20
21
22
23
2800
24
25
26
27
28
29
30
2800
31
            2800
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
2500
7
8
9
10
11
12
13
2500
14
15
16
17
18
19
20
2500
21
22
23
24
25
26
27
2500
28
29
30
        2500