Your browser's security settings have disabled Javascript, which is required to use this web site effectively.
Please alter your security settings. Click here to see how.

Aquinnah Vacation Rentals

info & map

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 hill.”

The Aquinnah >... more info and map.

Power Search

  

In a hurry? Use our Power SearchPower Search by date, price, amenities, and sift through 18 listings in seconds! to find in seconds what you want, when you want it, and within your budget!

  
By Property ID:

 

18 Vacation Properties in Aquinnah    sleeping 12, 11, 10, 9, 8, 6, 4, 3

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:
$4,000 - $5,200/wk,
$20,000 - $23,000/mo,

Off Season:
$3,000 - $4,500/wk,
$10,000 - $16,000/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, VCR or DVD, fireplace, high speed internet, pet-friendly

Time active on this website: 9 years, 5 months

Property ID# 3840, Listed by: Mark Harding

12 5 3
Owner Special: PRICE REDUCED ON AVAILABLE WEEKS THIS SUMMER! FLEX WEEKS IN AUGUST! NO FERRY HASSLES!
Aquinnah vacation rentals that sleep 11  

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$7,500 - $8,500/wk,

Off Season:
$3,900 - $6,500/wk,

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

Spectacular sunsets and views of the Vineyard Sound

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

Distance to beach: 1/2 Mile to Lobsterville Beach

Key amenities: view of salt water, deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet

Time active on this website: 7 months

Property ID# 20757, Listed by: Lighthouse Properties

11 6 3.5
Aquinnah vacation rentals that sleep 10  

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$10,000 - $11,000/wk,

Off Season:
$8,000 - $11,000/wk,

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

Lovely Up-Island Home with Swimming Pool

Set atop a hill overlooking Menemsha, Quitsa, and Squibnocket Ponds and the Atlantic Ocean beyond, rests this stunning home. A masterful combination of up-island elegance, fine craftsmanship, and expe....

Distance to beach: 2 miles to Philbin Beach, 1 mile to Lobsterville

Key amenities: view of salt water, screened porch, deck/porch/patio, pool, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet, handicap accessibility

Time active on this website: 8 years, 2 months

Property ID# 6042, Listed by: Pam Foster

10 5 4.5
Owner Special: Contact owner for discount on select weeks in June!

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$6,000 - $7,000/wk,
$22,000 - $24,000/mo,

Off Season:
$6,000/wk,
$20,000/mo,

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

Aquinnah Post and Beam with Waterviews: Short Walk to Beach

Situated at the end of a private road this five bedroom custom built post and beam has views of the Vineyard Sound and Elizabeth Islands. It offers many special places to sit and relax both inside and....

Distance to beach: 5 minute walk to Lobsterville Beach: white sand, g

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

Time active on this website: 1 year, 4 months

Property ID# 19630, Listed by: Lee

10 5 3

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$8,000 - $9,000/wk,

Off Season:
$6,000 - $8,000/wk,

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

Spectacular Up-Island Home with Ocean Views

This beautiful residence is situated on a private road with 4 acres of land and sweeping views of the Atlantic Ocean from most rooms. Enjoy beautiful sunsets from the decks and lovely views of the Ga....

Distance to beach: less than 1/2 mile to Philbin Beach

Key amenities: view of salt water, walk to a salt water beach, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, fireplace, high speed internet

Time active on this website: 1 month

Property ID# 21508, Listed by: Anne

10 5 6.5

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$3,000 - $3,800/wk,

Off Season:
$400 - $500/night,
$2,000 - $3,000/wk,

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

Get Away From It All In This Up-Island Waterview Home!

Come and enjoy the preservation of up-island in one of the most desirable locations on the Vineyard in this new 3-bedroom home with expansive water views of Vineyard Sound and the Elizabeth Islands. T....

Distance to beach: Dogfish Bar-3/10 mile, Lobsterville Beach 1/2mile,

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, VCR or DVD, fireplace, high speed internet, pet-friendly

Time active on this website: 3 years, 9 months

Property ID# 15748, Listed by: Joe

10 3 2.5
Owner Special: long weekend special!! 3 nights 4 days $1,000 !!
Aquinnah vacation rentals that sleep 9  

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$4,000 - $6,000/wk,

Off Season:
$2,000 - $5,500/wk,

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

New hillside home overlooking Vineyard Sound

Set on a hill overlooking Vineyard Sound and Menemsha Pond, this lovely new contemporary yet traditional home offers privacy, water views and a short walk to to 2 beaches. Lobsterville Beach on Vineya....

Distance to beach: .5 mile to Lobsterville Beach and Menemsha Pond

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

Time active on this website: 5 years, 6 months

Property ID# 11672, Listed by: Jim Wallen

9 4 3
Aquinnah vacation rentals that sleep 8  

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$3,300 - $3,900/wk,

Off Season:
$450 - $500/night,
$2,500 - $3,300/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 ....

Distance to beach: 1.25 miles to Philbin 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, VCR or DVD, fireplace, high speed internet, pet-friendly

Time active on this website: 11 years, 11 months

Property ID# 2945, Listed by: Patrick

8 4 2.5
Owner Special: Two weeks in August are still available for Summer 2012. Reserve your Vineyard vacation now.

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$3,750 - $4,000/wk,
$14,000/mo,

Off Season:
$4,000/wk,

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

No Man's View

Enjoy sweeping ocean views from this cozy, wooden home nestled on a private way just a short drive or bike to Lobsterville and Philbin Beaches. There is a large deck with a hot tub and four bedrooms ....

Distance to beach: 1 mile to Sound and ocean beaches

Key amenities: water view, deck/porch/patio, outdoor shower, hot tub, central A/C, washer&dryer, dishwasher, linens included, cable TV, VCR or DVD, high speed internet, pet-friendly

Time active on this website: 3 months

Property ID# 21135, Listed by: Kathy & Jim

8 4 2

Aquinnah, Gay Head

Aquinnah, Gay Head Martha's Vineyard vacation rental

Summer:
$2,500 - $3,500/wk,
$14,000/mo,

Off Season:
$300 - $400/night,
$2,000 - $3,500/wk,
$8,000 - $12,000/mo,

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, VCR or DVD, fireplace, pet-friendly

Time active on this website: 3 years, 9 months

Property ID# 7861, Listed by: Karen

8 3 2

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$2,100 - $2,700/wk,
$7,000 - $8,000/mo,

Off Season:
$1,000 - $2,150/wk,
$4,000 - $5,000/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, VCR or DVD, high speed internet, pet-friendly, handicap accessibility

Time active on this website: 2 years, 4 months

Property ID# 18144, Listed by: Leslie Ekings

8 3 2
Aquinnah vacation rentals that sleep 6  

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$1,000 - $2,300/wk,
$8,100 - $8,900/mo,

Off Season:
$500 - $1,200/wk,
$1,800 - $3,950/mo,

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

Pancake Hollow

This lovely home, secluded on 7 acreas, 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 ....

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, VCR or DVD, fireplace, high speed internet, handicap accessibility

Time active on this website: 10 years

Property ID# 3557, Listed by: Jestina Held

6 3 3

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$2,000/wk,

Off Season:
$2,000/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, cable TV, VCR or DVD, fireplace, high speed internet, pet-friendly

Time active on this website: 1 year, 6 months

Property ID# 17641, Listed by: Paige

6 3 1

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$1,600 - $1,800/wk,

Off Season:
$1,600/wk,

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

Charming three bedroom Aquinnah Cottage

This charming three bedroom cottage is in a convenient location, equidistant to all wonderful activities that Aquinnah has to offer! Enjoy the rolling surf and sugar sand dunes at Philbin Beach or pu....

Distance to beach: 3 Miles to Philbin Beach

Key amenities: deck/porch/patio, outdoor shower, dishwasher, cable TV, VCR or DVD

Time active on this website: 7 months

Property ID# 20750, Listed by: Lighthouse Properties

6 3 2

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$2,500 - $3,900/wk,

Off Season:
$2,000 - $2,500/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, VCR or DVD, high speed internet

Time active on this website: 4 months

Property ID# 21097, Listed by: Susan

6 3 2

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$4,000/wk,

Off Season:
$1,800 - $4,000/wk,

Summer Island Style

A beach cottage set in the dunes amidst waving sea grasses with the scent of roses in the air. This architect-designed 4 bedroom home offers wide panoramic waterviews of the sparkling northshore with ....

Distance to beach: 1/2mile to Lobsterville Beach

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

Time active on this website: 3 years, 6 months

Property ID# 16048, Listed by: Conroy & Company

6 3 2
Aquinnah vacation rentals that sleep 4  

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$1,800 - $2,250/wk,

Off Season:
$1,800/wk,

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

Spectacular Ocean View - Walk to Beach and Cliffs

Spectacular ocean views greet you from both the front and the rear of this property. This tastefully decorated 2 bedroom private end unit condominium is within walking distance to one the most beautif....

Distance to beach: Walk to Moshup Beach ( Land Bank 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, VCR or DVD, high speed internet

Time active on this website: 4 years, 4 months

Property ID# 11989, Listed by: Roger

4 2 2
Owner Special: Special rate for 2 weeks in August -- $2100 per week.
Aquinnah vacation rentals that sleep 3  

Aquinnah

Aquinnah Martha's Vineyard vacation rental

Summer:
$1,800 - $2,000/wk,

Off Season:
$1,400 - $1,800/wk,

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

Walk to Beach - Water Views

Generously sized, one bedroom house overlooking Lobsterville Beach in scenic Gay Head (Aquinnah). Spectacular water views up Vineyard Sound to the far away lights of Cape Cod. Simple modern furnis....

Distance to beach: 1/4 mile, 10 minute walk to Lobsterville Beach

Key amenities: view of salt water, walk to a salt water beach, screened porch, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, high speed internet, handicap accessibility

Time active on this website: 1 year, 1 month

Property ID# 20089, Listed by: Kathleen

3 1 1