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Aquinnah, formerly called Gay Head, is the western most area of Martha's Vineyard. Aquinnah, West Tisbury, and Chilmark are often referred to as "up-island." This region is rural and unspoiled, with stone walls, farms, and vineyards.

12 Vacation Properties in Aquinnah
Sleeps

Aquinnah vacation rentals that sleep 12

Aquin-Jan
ID 38843
5 BR
3 ½ baths
Sleeps 12
Luxurious New Post & Beam Waterview in Aquinnah
Luxurious New Post & Beam Waterview in Aquinnah
Distance to beach: 0.9 mi to Gay Head Cliffs and Beach and 1 mi Lobsterville Beach
OWNER SPECIAL:
Lots of availability for 2025! STUNNING HOME!!!First FULL SEASON!
Summer:
$12,000 - $15,000/wk
Off Season:
$12,000 - $15,000/wk
2

Aquinnah vacation rentals that sleep 10

Aquinnah
ID 19630
5 BR
3 baths
Sleeps 10
Aquinnah Skye Ln: Walk to Beach, WaterView, Central A/C WiFi
Aquinnah Skye Ln: Walk to Beach, WaterView, Central A/C WiFi
Distance to beach: 5-10 minute walk to Lobsterville Beach
7 reviews read reviews
Summer:
$8,000 - $8,500/wk
Off Season:
$7,000 - $8,000/wk
6
Aquinnah
ID 33889
4 BR
2 baths
Sleeps 10
''Aquinnah Paradise'' Right on the Water. Great Views!
''Aquinnah Paradise'' Right on the Water. Great Views!
Distance to beach: 2 minute walk to semi-private beach,
4 reviews read reviews
Summer:
$7,000/wk
Off Season:
$500/night
$7,000/wk
3
Aquinnah
ID 38232
4 BR
3 baths
Sleeps 10
Aquinnah Home with Meadow and Light House Views
Aquinnah Home with Meadow and Light House Views
Distance to beach: 1 mile Gay Head Public (Moshup Beach) and 1.3 mile Philbin Beach
2 reviews read reviews
OWNER SPECIAL:
JUST REDUCED! Prices dropped $1K October availability! Perfect for the Derby! Pet friendly!
Summer:
$500 - $750/night
$3,500 - $5,000/wk
Off Season:
$430 - $660/night
$3,000 - $4,500/wk
3

Aquinnah vacation rentals that sleep 9

Aquinnah
ID 31967
5 BR
2 baths
Sleeps 9
Panoramic Water Views, Quiet Private Up-island Location
Panoramic Water Views, Quiet Private Up-island Location
Distance to beach: 4/10 mi to Lobsterville Beach and 4/10 mi to Menemsha Pond - Red Beach
Summer:
$5,000 - $5,500/wk
Off Season:
$4,200/wk
3
Aquinnah
ID 11672
4 BR
3 baths
Sleeps 9
Hillside home overlooking Vineyard Sound
Hillside home overlooking Vineyard Sound
Distance to beach: .5 mile to Lobsterville Beach and Menemsha Pond
7 reviews read reviews
Summer:
$7,500 - $8,000/wk
Off Season:
$5,000 - $7,000/wk
$20,000/mo
3

Aquinnah vacation rentals that sleep 8

Aquinnah
ID 34177
4 BR
2 ½ baths
Sleeps 8
Water-view Aquinnah Home on 13 acres
Water-view Aquinnah Home on 13 acres
Distance to beach: 1.0 mi to Gay Head Cliffs and Beach
1 review read review
Summer:
$4,200 - $5,656/wk
Off Season:
$4,200 - $5,656/wk
Tashtego's Tree House
ID 34490
3 BR
2 ½ baths
Sleeps 8
Tashtego's Tree House
Tashtego's Tree House
Distance to beach: 1.5 mile to Gay Head Public (Moshup Beach) and 2 mile to Philbin Beach
6 reviews read reviews
Summer:
$3,300 - $3,400/wk
Off Season:
$3,300/wk
Aquinnah
ID 35479
3 BR
2 ½ baths
Sleeps 8
Aquinnah Summer Home
Aquinnah Summer Home
Distance to beach: 1.5 miles Lobsterville Beach and 1.2 miles Philbin Beach
Summer:
$3,000 - $5,000/wk
$16,000 - $18,000/mo
Off Season:
$3,000 - $4,500/wk
$10,000 - $14,000/mo
6

Aquinnah vacation rentals that sleep 6

Aquinnah
ID 35223
3 BR
3 baths
Sleeps 6
Beautiful Aquinnah Home, Walk to Beach, Partial Ocean View
Beautiful Aquinnah Home, Walk to Beach, Partial Ocean View
Distance to beach: 1/10 or less mile to private town beach Philbin Beach and 1 mile with our permit to lobsterville, red beach Lobsterville Beach
5 reviews read reviews
Summer:
$4,650/wk
Off Season:
$3,400 - $4,650/wk
5
Aquinnah
ID 36841
3 BR
2 baths
Sleeps 6
Quiet, Secluded with Panoramic Views
Quiet, Secluded with Panoramic Views
Distance to beach: 1 mile Philbin Beach
Summer:
$4,500 - $6,000/wk
Off Season:
$4,500 - $6,000/wk
2

Aquinnah vacation rentals that sleep 5

Aquinnah
ID 35941
3 BR
2 baths
Sleeps 5
Charming Aquinnah Cottage
Charming Aquinnah Cottage
Distance to beach: 1.6 mi to Gay Head Cliffs and Beach and 1.7 mi to Lobsterville Beach
Summer:
$2,500 - $3,400/wk
Off Season:
$2,500 - $3,000/wk