Aquinnah

Aquinnah is the westernmost and furthest up-island town on the island offering some of the most private escapes. Nothing is more magical than the Aquinnah shoreline, the Gay Head lighthouse and colorful clay cliffs. While it's a 30-minute drive to any of the down-inland towns there is plenty to do in and around Aquinnah. There are small shops on the cliffs, stunning beaches and lots of walking trails for nature lovers to enjoy. The Outermost Inn set above the cliffs on Lighthouse Road, is a must stop for a superb dining experience in an amazing setting. Orange Peel Bakery on State Road offers fresh baked bread and other treats and the popular build-your-own pizza nights. Menemsha Village is just on the other side of Menemsha Pond and Chilmark center, where you can dine at the Chilmark Tavern or grab groceries at the Chilmark Store, is about 8 minutes away. If you're looking for a location where you can truly un-plug, Aquinnah may be the spot, reach out and we can help you find your next summer getaway.


Properties Available 8 properties available
This Martha's Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. Four bedroom custom home which overlooks the Vineyard Sound, offering breathtaking panoramic views to the Elizabeth Islands. With state of the art decor and interior furnishings, guests will enjoy environmentally sensitive,
Aquinnah Pet Friendly
$35,000.00 / per week
Beds 4 beds
Baths 4 Full, 1 Half Bath
Sleeps 8 sleeps
Aquinnah 2501
This Martha's Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. Four bedroom custom home... Read More
June 2027
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    1 2 3 4 $35000 5
6 7 8 9 10 11 $35000 12
13 14 15 16 17 18 $35000 19
20 21 22 23 24 25 $35000 26
27 28 29 30      
July 2027
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        1 2 $35000 3
4 5 6 7 8 9 $35000 10
11 12 13 14 15 16 $35000 17
18 19 20 21 22 23 $35000 24
25 26 27 28 29 30 $35000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $35000 7
8 9 10 11 12 13 $35000 14
15 16 17 18 19 20 $35000 21
22 23 24 25 26 27 $35000 28
29 30 31        
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A contemporary three-bedroom home, offering distant water views and access to the beautiful Aquinnah beaches! This house includes three bedrooms, two on the lower level which open to outside, as well as an additional bedroom on the second floor with dual ensuite bathrooms and a sitting area with television. If you are looking for more space look at
Hot HOT 21
Aquinnah
$3,000.00 - $4,800.00 / per week
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps 7 sleeps
Aquinnah 2507
A contemporary three-bedroom home, offering distant water views and access to the beautiful Aquinnah beaches! This house includes three bedrooms, two ... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $3500 5
6 7 8 9 10 11 $4300 12
13 14 15 16 17 18 $4300 19
20 21 22 23 24 25 $4300 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $4300 3
4 5 6 7 8 9 $4300 10
11 12 13 14 15 16 $4300 17
18 19 20 21 22 23 $4800 24
25 26 27 28 29 30 $4800 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $4800 7
8 9 10 11 12 13 $4800 14
15 16 17 18 19 20 $4600 21
22 23 24 25 26 27 $3500 28
29 30 31        
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This lovely three bedroom home in Aquinnah, with breathtaking water views is a fabulous summer rental for those that love the rural up island setting of Martha's Vineyard. The owners have an Aquinnah parking pass available for each tenant, this pass allows parking at Lobsterville Beach, Menemsha Pond and West Basin. This home offers a truly specia
Hot HOT 17
Aquinnah Pet Friendly
$3,000.00 - $4,800.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 4 (1)
Aquinnah 2521
This lovely three bedroom home in Aquinnah, with breathtaking water views is a fabulous summer rental for those that love the rural up island setting ... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $3500 5
6 7 8 9 10 11 $4300 12
13 14 15 16 17 18 $4300 19
20 21 22 23 24 25 $4300 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $4300 3
4 5 6 7 8 9 $4300 10
11 12 13 14 15 16 $4300 17
18 19 20 21 22 23 $4800 24
25 26 27 28 29 30 $4800 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 $4600 21
22 23 24 25 26 27 $3500 28
29 30 31        
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This 4 bedroom Aquinnah home perched on a hilltop offers sweeping views of Vineyard Sound and is the prefect up-island getaway. The Main Level has open Kitchen, Living and Dining Spaces, an office and the first of the four bedrooms. Upstairs is the primary en suite and the other 2 bedrooms share a hall bath. Enjoy the cool summer breeze from the up
Aquinnah Pet Friendly
$5,500.00 - $8,500.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Aquinnah 2505
This 4 bedroom Aquinnah home perched on a hilltop offers sweeping views of Vineyard Sound and is the prefect up-island getaway. The Main Level has ope... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $6000 5
6 7 8 9 10 11 $8000 12
13 14 15 16 17 18 $8000 19
20 21 22 23 24 25 $8000 26
27 28 29 30      
July 2027
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        1 2 $8000 3
4 5 6 7 8 9 $8000 10
11 12 13 14 15 16 $8000 17
18 19 20 21 22 23 24
25 26 27 28 29 30 $8500 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $8500 7
8 9 10 11 12 13 $8500 14
15 16 17 18 19 20 $8500 21
22 23 24 25 26 27 $7000 28
29 30 31        
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This fully modernized 19th century farmhouse is situated on six acres in Aquinnah, and set on one of the highest points on the island. Multiple nature paths surround this unique property. One bedroom on the main floor with the other bedrooms located on the second level. Peaks of water views from almost every room. Rambling stonewalls, wisteria-cove
Aquinnah
$7,300.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 5 sleeps
Aquinnah 2515
This fully modernized 19th century farmhouse is situated on six acres in Aquinnah, and set on one of the highest points on the island. Multiple nature... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $7300 5
6 7 8 9 10 11 $7300 12
13 14 15 16 17 18 $7300 19
20 21 22 23 24 25 $7300 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $7300 3
4 5 6 7 8 9 $7300 10
11 12 13 14 15 16 $7300 17
18 19 20 21 22 23 $7300 24
25 26 27 28 29 30 $7300 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $7300 7
8 9 10 11 12 13 $7300 14
15 16 17 18 19 20 $7300 21
22 23 24 25 26 27 $7300 28
29 30 31        
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Unparalleled views overlooking Moshup beach, this stunning home has some of the most spectacular views available on the Vineyard. High end amenities throughout, with exquisite detail in every sense. The bedding, linens, and decor are all top of the line. Each bedroom is en suite, and each level has a family room with smart tv's. The multi level wra
Aquinnah
$11,000.00 - $22,000.00 / per week
Beds 4 beds
Baths 4 Full, 1 Half Bath
Sleeps 10 sleeps
Aquinnah 2502
Unparalleled views overlooking Moshup beach, this stunning home has some of the most spectacular views available on the Vineyard. High end amenities t... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $11000 5
6 7 8 9 10 11 $11000 12
13 14 15 16 17 18 $16500 19
20 21 22 23 24 25 $19800 26
27 28 29 30      
July 2027
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        1 2 $19800 3
4 5 6 7 8 9 $19800 10
11 12 13 14 15 16 $22000 17
18 19 20 21 22 23 $22000 24
25 26 27 28 29 30 $22000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $22000 7
8 9 10 11 12 13 $22000 14
15 16 17 18 19 20 $22000 21
22 23 24 25 26 27 $21057 28
29 30 31        
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A contemporary five-bedroom home with main and guest house, offering distant water views and access to the beautiful Aquinnah beaches! Main House includes three bedrooms, two on the lower level which open to outside, as well as an additional bedroom on the second floor with dual ensuite bathrooms and a sitting area with television. The Guest House,
Hot HOT 34
Aquinnah
$5,900.00 - $7,250.00 / per week
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps 10 sleeps
Rating 4.2 (4)
Aquinnah 2503
A contemporary five-bedroom home with main and guest house, offering distant water views and access to the beautiful Aquinnah beaches! Main House incl... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $5900 5
6 7 8 9 10 11 $5900 12
13 14 15 16 17 18 $5900 19
20 21 22 23 24 25 $6900 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $6900 3
4 5 6 7 8 9 $6900 10
11 12 13 14 15 16 $6900 17
18 19 20 21 22 23 $6900 24
25 26 27 28 29 30 $7250 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $7250 7
8 9 10 11 12 13 $7250 14
15 16 17 18 19 20 $7250 21
22 23 24 25 26 27 $5900 28
29 30 31        
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This spacious and uniquely designed home blends classic Vineyard character with modern luxury. The main level showcases timeless wood details and charm, seamlessly complemented by updated bathrooms, a thoughtfully renovated kitchen and three bedrooms one of which is an en suite while the other two share a hall bath and powder room. The warm and wel
Aquinnah
$5,000.00 - $11,500.00 / per week
Beds 6 beds
Baths 5 Full, 1 Half Bath
Sleeps 13 sleeps
Rating 5 (1)
Aquinnah 2504
This spacious and uniquely designed home blends classic Vineyard character with modern luxury. The main level showcases timeless wood details and char... Read More
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 $9000 5
6 7 8 9 10 11 $9000 12
13 14 15 16 17 18 $9000 19
20 21 22 23 24 25 $9000 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 $11500 3
4 5 6 7 8 9 $11000 10
11 12 13 14 15 16 $11000 17
18 19 20 21 22 23 $11000 24
25 26 27 28 29 30 $11000 31
August 2027
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $11000 7
8 9 10 11 12 13 $11000 14
15 16 17 18 19 20 $11000 21
22 23 24 25 26 27 $11000 28
29 30 31        
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