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Aquinnah Vacation Rentals

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.

The native Wampanoag tribe is credited with providing this area with much history. One of the few Indian townships in Massachusetts, Aquinnah means “land beneath the ... more info and map.

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10 Vacation Properties in Aquinnah    sleeping 12, 11, 10, 8, 6, 5

Location Price Description (click blue title for more...) Sleeps BRs Baths
Aquinnah vacation rentals that sleep 12  

Aquinnah / Gay Head

Aquinnah / Gay Head Martha's Vineyard vacation rental

Summer:
$3,500 - $5,000/night,
$4,500 - $5,000/wk,

Off Season:
$350 - $600/night,
$3,500 - $5,000/wk,
$13,000/mo,

See a full calendar with detailed availability and pricing for this Aquinnah vacation rental.

Cooper's Spring

Tucked away in a grove of mature sassafras and beetlebung trees, this private oak post and beam home is situated on a high hill overlooking the Gay Head lighthouse with sweeping vistas of the Atlantic....

Distance to beach: 1/4 mile to Maushop Beach;1/2 mile to Philbin Bch

Key amenities: view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, jacuzzi, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly

Time active on this website: 10 years, 9 months

Property ID# 3840, Listed by: Mark Harding

12 5 3
Owner Special: JULY DATES AVAILABLE, PLEASE CALL FOR REDUCED RATES AND SCHEDULE!!
Aquinnah vacation rentals that sleep 11  

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$4,000 - $8,500/wk,
$21,500 - $27,500/mo,

Off Season:
$700 - $800/night,
$4,000 - $6,500/wk,

See a full calendar with detailed availability and pricing for this Aquinnah vacation rental.

Aquinnah Dream Location, Stunning Water Views & Central AC

This home is a beautifully decorated and appointed private residence with many comforts and conveniences and is one of the premier vacation rentals on Martha's Vineyard. Spectacular sunsets & ethereal....

Distance to beach: 7/10 mile Philbin Beach

Key amenities: view of salt water, walk to a salt water beach, screened porch, deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet

Time active on this website: 1 year, 2 months

Property ID# 23078, Listed by: Pat

11 6 4.5
Aquinnah vacation rentals that sleep 10  

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$5,000 - $6,500/wk,
$18,000 - $24,000/mo,

Off Season:
$4,000 - $5,000/wk,
$15,000 - $17,000/mo,

See a full calendar with detailed availability and pricing for this Aquinnah vacation rental.

Aquinnah Skye Post & Beam, Water View, Short Walk to Beach

LAST MINUTE $500 OFF ALL UNSOLD WEEKS. SEE NEW RATES BELOW. PLEASE SCROLL DOWN. Location: 4 Skye Lane, Aquinnah, Martha's Vineyard. Situated at the end of a private road this five bedroom custom buil....

Distance to beach: 5-minute walk to Lobsterville Beach

Key amenities: view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet

Time active on this website: 3 years, 4 months

Guest Reviews: 1

Property ID# 19630, Listed by: Lee

10 5 3
Owner Special: $500 reduction. July 11-18. Was $5500 now only $5000. Plus cleaning. Beautiful home. Come enjoy.
Aquinnah vacation rentals that sleep 8  

Aquinnah, Martha's Vineyard

Aquinnah, Martha's Vineyard Martha's Vineyard vacation rental

Summer:
$3,000 - $3,900/wk,

Off Season:
$450 - $500/night,
$2,500 - $3,900/wk,

See a full calendar with detailed availability and pricing for this Aquinnah vacation rental.

Up-Island Charm with an Ocean View

Down a private country road, this bright and breezy post & beam home sits on a 3-acre rolling wooded parcel. With southern views of the Atlantic Ocean, it's just a short drive or bike to Philbin and ....

Distance to beach: 1.25 miles to Philbin Beach and Lobsterville Beach

Key amenities: view of salt water, screened porch, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly

Time active on this website: 14 years

Property ID# 2945, Listed by: Patrick

8 4 2.5
Owner Special: July 8-19 still available! Reduced to $3000 per week (a $900 discount). Call 312-909-4496 to book.

Aquinnah, Gay Head-on lighthouse rd

Aquinnah, Gay Head-on lighthouse rd Martha's Vineyard vacation rental

Summer:
$3,500/wk,

Off Season:
$300/night,
$600 - $3,500/wk,

See a full calendar with detailed availability and pricing for this Aquinnah vacation rental.

Wonderful Up-Island House with Panoramic Water Views

This wonderful house, perched near the top of the hill on Lighthouse Road in Aquinnah/Gay Head, is available for most weeks in the summer and September. Its location and a large wrap-around deck prov....

Distance to beach: 1 mile to Philbin Beach, 1 mile to Lobsterville

Key amenities: view of salt water, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, pet-friendly

Time active on this website: 4 years, 11 months

Guest Reviews: 3

Property ID# 7861, Listed by: Karen

8 3 2

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$2,000 - $2,700/wk,
$10,000/mo,

Off Season:
$1,800 - $2,100/wk,
$6,000/mo,

See a full calendar with detailed availability and pricing for this Aquinnah vacation rental.

Sunny, Cozy 3 Bedroom Home with Ocean Views

This is a charming, contemporary home located on one secluded, well-landscaped acre of yard, ready for your family's vacation needs. Inside you will find 3 levels of open, sunny living space featuring....

Distance to beach: Less than 2 miles to Philbin Beach

Key amenities: view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, pet-friendly, handicap accessibility

Time active on this website: 4 years, 6 months

Guest Reviews: 5

Property ID# 18144, Listed by: Leslie Ekings

8 3 2
Aquinnah vacation rentals that sleep 6  

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$1,200 - $2,350/wk,

Off Season:
$800 - $2,350/wk,
$2,200 - $4,000/mo,

See a full calendar with detailed availability and pricing for this Aquinnah vacation rental.

Pancake Hollow: 3 BR/3BT w/Central AC on 7 Serene Acres

This lovely home, secluded on 7 acres, features cathedral ceilings, a screened porch ideal for morning reading, and a large deck. The three bedrooms are zoned for privacy, with one on each end o....

Distance to beach: Philbin and Lobsterville beaches within 2 miles

Key amenities: screened porch, deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, handicap accessibility

Time active on this website: 12 years, 11 months

Guest Reviews: 9

Property ID# 3557, Listed by: Jestina Held

6 3 3

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$2,100 - $2,300/wk,

Off Season:
$400 - $600/night,
$1,300 - $2,300/wk,

See a full calendar with detailed availability and pricing for this Aquinnah vacation rental.

Walk to Beautiful Island Beach from This Secluded Retreat

This comfortable, secluded vacation home offers you the chance to enjoy island living at its best. Walk to one of the Island's most beautiful beaches at a moment's notice. Grill a delicious dinner o....

Distance to beach: 5 minute walk to Moshup's Beach and the Cliffs

Key amenities: view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly

Time active on this website: 3 years, 8 months

Property ID# 17641, Listed by: Paige

6 3 1

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$3,300 - $4,100/wk,

Off Season:
$2,500 - $3,000/wk,

See a full calendar with detailed availability and pricing for this Aquinnah vacation rental.

Secluded & romantic with spectacular views, 2009 renovation

Wake up on one of the highest elevations in Aquinnah (marked as Molasha Hill in mid 1800’s coastal surveys), and watch the sun rise over the panoramic Atlantic view which extends from Squibnocket Poin....

Distance to beach: Philbin Beach (1 mi), Lobsterville Beach (1 mi)

Key amenities: view of salt water, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet

Time active on this website: 2 years, 5 months

Guest Reviews: 3

Property ID# 21097, Listed by: Susan

6 3 2
Aquinnah vacation rentals that sleep 5  

Aquinnah Beach Front

Aquinnah Beach Front Martha's Vineyard vacation rental

Summer:
$500 - $840/night,
$5,250 - $5,900/wk,
$18,000 - $19,500/mo,

Off Season:
$1,500 - $5,900/wk,

See a full calendar with detailed availability and pricing for this Aquinnah vacation rental.

Spectacular Beach Front Property

One-of-a-kind waterfront location!! Celebrities and Honeymooners have often selected to stay here. 12 1/2 acres of privacy includes your own beach, sunsets over the water, premier fishing, and a f....

Distance to beach: House is directly on the Dogfish Bar beach.

Key amenities: on a salt water beach, hot tub, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, handicap accessibility

Time active on this website: 4 years, 5 months

Guest Reviews: 2

Property ID# 3401, Listed by: Deborah

5 3 2