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 7 properties available
This spacious and uniquely designed home blends classic Vineyard character with modern luxury. The original portion of the house showcases timeless wood details and charm, seamlessly complemented by updated bathrooms, a thoughtfully renovated kitchen and two en suite bedrooms, both on the main level. Beyond the living room, the newer wing offers a
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 original portion of the house showcases timeless wo... Read More
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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 2026
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This Martha's Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. New 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 sensiti
Aquinnah Pet Friendly
Beds 4 beds
Baths 3 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. New four bedroom custom ... Read More
June 2026
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  1 2 3 4 5 $35000 6
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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. Spectacular water views from almost every room. Rambling stonewalls, wisteria-c
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
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            $7300 1
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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
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 2026
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  1 2 3 4 5 $3500 6
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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
$13,200.00 - $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 2026
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  1 2 3 4 5 $11000 6
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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,
Aquinnah
$6,900.00 - $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
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12 13 14 15 16 17 $6900 18
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