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 9 properties available
BR1 Queen, First FloorHall Bath with Shower, First FloorBR2 Queen, First FloorBR3 King En Suite with Shower, First FloorBR4 (3) Twins En Suite with Shower, Second FloorBR5 Queen En Suite with Shower, Lower LevelBR6 King En Suite with Shower Tub Combo, Lower Level
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 distinctive home boasts an impressive design throughout. The left side features the original residence, rich in classic details and ... Read More
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BR1 King En Suite with Shower Stall, Lower LevelBR2 Queen, Lower LevelHall Bath with Shower Stall, Lower LevelBR3 Queen, Lower LevelBR4 Double & (2) Twin Beds, Lower LevelHall Bath with Shower Tub Combo, Lower Level
Aquinnah
$4,500.00 - $7,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 9 sleeps
Aquinnah 2512
Situated at the Westernmost tip of the island, this 4 bedroom reverse contemporary beach home is perfect for your next getaway with family and friends... Read More
June 2025
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1 2 3 4 5 6 $5200 7
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BR1 King En Suite with Shower Stall and Tub, Half Floor above First FloorBR2 King En Suite with Shower, Lower LevelBR3 (2) Bunk beds En Suite with Shower Tub Combo, Lower LevelBR4 King En Suite with Shower, Lower LevelLaundry Facilities, Lower Level
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 2025
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1 2 3 4 5 6 $11000 7
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15 16 17 18 19 20 $16500 21
22 23 24 25 26 27 $19800 28
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    1 2 3 4 $19800 5
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BR1 Queen, Second FloorBR2 Queen & Twin Bed, Lower Level Hall bath with Shower StallBR3 Queen, Lower LevelBR4 Guesthouse Queen and BR5 Guesthouse QueenHall bath with Shower Tub Combo
Aquinnah
$6,700.00 - $7,000.00 / per week
Beds 5 beds
Baths 4 Full, 1 Half Bath
Sleeps 10 sleeps
Rating 4.3 (3)
Aquinnah Main and Guest House 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 2025
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1 2 3 4 5 6 $7000 7
8 9 10 11 12 13 $7000 14
15 16 17 18 19 20 $7000 21
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BR1 King En Suite with Separate Tub and Shower Stall, First FloorBR2 Queen En Suite with Shower Stall, Lower LevelBR3 (2) Twin Beds, Lower LevelBR4 Bunk Bed (Twin/Double), Lower LevelHall Bath with Shower Tub Combo, Lower Level
Aquinnah Pet Friendly
$35,000.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Aquinnah 2501
Two week minimum. This Martha's Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. New fo... Read More
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1 2 3 4 5 6 $35000 7
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    1 2 3 4 $35000 5
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BR1 Queen En Suite with Shower Stall, Second FloorBR2 Queen, Second FloorBR3 (2) Twins, Second FloorHall Bath with Shower Tub Combo, Second FloorPowder Room, First Floor
Aquinnah Pet Friendly
$6,250.00 - $6,500.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 6 sleeps
Aquinnah 2506
Check-in to this serene Aquinnah home and watch your worries drift away with the wind. Take full advantage of the cool Island breeze by opening one of... Read More
June 2025
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1 2 3 4 5 6 $6250 7
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BR1 King En Suite with Shower, First FloorBR2 Queen, Lower LevelBR3 (2) Doubles, Lower LevelHall bath with Shower Tub Combo, Lower LevelPowder Room, First Floor
Hot HOT 10
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 2025
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BR1 Queen, First FloorHall bath with Shower Tub Combo, First FloorBR2 Twin Daybed, Second FloorBR3 Queen, Second FloorHall bath with Shower Tub Combo, Second Floor
Aquinnah
$6,800.00 / 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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BR1 King En Suite with Shower Stall and Tub, Second FloorBR2 Queen, Second FloorBR3 (2) Twins, Second FloorBR4 Queen, First FloorHall bath, Second FloorHall bath with Shower, First Floor
Aquinnah Pet Friendly
$5,000.00 - $8,400.00 / 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
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24 25 26 27 28 29 $6000 30
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