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.
  • Locations
  • Dates
  • Price
  • Bedrooms / Sleeps
  • Proximity to Water
  • Exterior Amenities
  • Interior Amenities
  • Area Amenities
 
Advanced Options
Locations
Locations
+ multiple towns
Click on an area of the map in order to see it in more detail.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Dates
Dates
Nights in Your Stay
If you have flexible arrival and/or departure dates, put the first possible arrival date and last possible departure date in the date fields above. We'll search for your number of nights in between
By Week (compare up to 4 weeks)
Pick your season
Tell Us More About Your Trip (optional)
Number of Weeks
Starting On What Day?
Search and compare up to 4 weeks in one season
Only 4 weeks may be selected at one time.
By Entire Months
Number of months
Pick the starting month
  • January
    2018
  • February
    2018
  • March
    2018
  • April
    2018
  • May
    2018
  • June
    2018
  • July
    2018
  • August
    2018
  • September
    2018
  • October
    2018
  • November
    2018
  • December
    2018
  • January
    2019
  • February
    2019
  • March
    2019
  • April
    2019
  • May
    2019
  • June
    2019
  • July
    2019
Price
Price
Any
Bedrooms / Sleeps
Bedrooms / Sleeps
Bedrooms
Sleeps
+
Proximity to Water
Proximity to Water
  •  (½ mi. or less)
    * ½ mi. or less
     (½ mi. or less)
Exterior
Exterior
Interior
Interior
Area amenities
Area amenities
 

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.

9 Vacation Properties in Aquinnah
Sleeps

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
Distance to beach: 5-10 minute walk to Lobsterville Beach
4 reviews read reviews
Description
Location: 4 Skye Lane, Aquinnah, Martha's Vineyard. Situated at the end of a private road, this five-bedroom, custom-built post and beam home has views of Vineyard Sound and Elizabeth Islands. It offe... read more
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, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
6 years, 9 months
Property ID 19630 listed by: Lee
Summer:
$6,000 - $7,500/wk
Off Season:
$5,000 - $5,500/wk

Aquinnah vacation rentals that sleep 9

Aquinnah
ID 11672
4 BR
3 baths
Sleeps 9
Hillside home overlooking Vineyard Sound
Distance to beach: .5 mile to Lobsterville Beach and Menemsha Pond
7 reviews read reviews
Description
Set on a hill overlooking Vineyard Sound and Menemsha Pond, this lovely contemporary yet traditional home offers privacy, water views and a short walk to to 2 beaches. Lobsterville Beach on Vineyard ... read more
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, DVD or VCR, fireplace, wireless or wired internet, pet-friendly, handicap accessibility
Time active on this website
7 years, 2 months
Property ID 11672 listed by: Jim Wallen
Summer:
$4,000 - $7,000/wk
Off Season:
$2,000 - $5,000/wk

Aquinnah vacation rentals that sleep 8

Aquinnah, Martha's Vineyard
ID 2945
4 BR
2 ½ baths
Sleeps 8
Up-Island Charm with an Ocean View
Distance to beach: 1.25 miles to Philbin Beach and Lobsterville Beach
Description
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 ... read more
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
17 years, 6 months
Property ID 2945 listed by: Patrick
Summer:
$4,000 - $4,100/wk
Off Season:
$550 - $650/night
$3,200 - $4,000/wk
Aquinnah
ID 25630
4 BR
3 baths
Sleeps 8
Waterviews,Walk to Beach Birding Fish Bike Avail 2018
Distance to beach: Vineyard Sound/Lobsterville Bch 1/4 mile
Description
Great water views, short walk to beaches and fishing off Dogfish Bar are yours with our contemporary house in Aquinnah on Martha's Vineyard. Enjoy a 180 degree panoramic view of Vineyard Sound, the El... read more
Key amenities
view of salt water, walk to a salt water beach, screened porch, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, cable TV, DVD or VCR, wireless or wired internet, pet-friendly
Time active on this website
2 years, 4 months
Property ID 25630 listed by: Bob
Summer:
$1,680 - $3,600/wk
Off Season:
$220 - $320/night
$1,400 - $2,310/wk

Aquinnah vacation rentals that sleep 7

Aquinnah
ID 27277
3 BR
2 ½ baths
Sleeps 7
Aquinnah Panoramic Waterviews
Distance to beach: 1/2 Mi to Lobsterville Beach, Philbin Beach
Description
Great water view property in Aquinnah - this immaculate contemporary has that unique combination of a beautifully designed and constructed, year-round home, AND an outstanding view of the Sound and El... read more
Key amenities
view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
11 months
Property ID 27277 listed by: Keri at Karen M. Overtoom Real Estate
Summer:
$3,500 - $4,000/wk
Off Season:
$3,000 - $3,500/wk

Aquinnah vacation rentals that sleep 6

Aquinnah
ID 18144
3 BR
2 baths
Sleeps 6
Sunny, Cozy 3 Bedroom Home with Ocean Views
Distance to beach: 1/2 m. to Lobsterville; < 2 miles to Philbin Be
8 reviews read reviews
Description
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... read more
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
8 years
Property ID 18144 listed by: Leslie Ekings
Summer:
$2,200 - $2,700/wk
Off Season:
$1,800 - $2,200/wk
Aquinnah
ID 17641
3 BR
1 bath
Sleeps 6
Walk to Beautiful Island Beach from This Secluded Retreat
Distance to beach: 5 minute walk to Moshup's Beach and the Cliffs
Description
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... read more
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
7 years, 2 months
Property ID 17641 listed by: Paige
Summer:
$2,400/wk
Off Season:
$500/night
$2,000 - $2,200/wk
Aquinnah
ID 29382
3 BR
2 baths
Sleeps 6
Quiet, Secluded with Panoramic Views
Distance to beach: Philbin Beach 1 mile
OWNER SPECIAL:
Ferry Tickets available! Please email owner for details.
Description
Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Bea... read more
Key amenities
view of salt water, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, wireless or wired internet, pet-friendly
Time active on this website
Less than a month
Property ID 29382 listed by: Victoria
Summer:
$600 - $715/night
$4,200 - $5,000/wk
Off Season:
$350 - $450/night
$2,450 - $3,500/wk
Aquinnah
ID 3557
3 BR
3 baths
Sleeps 6
Pancake Hollow: 3 BR/3BT w/Central AC on 7 Serene Acres
Distance to beach: Philbin and Lobsterville beaches within 2 miles
14 reviews read reviews
Description
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... read more
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
16 years, 5 months
Property ID 3557 listed by: Jestina Held
Summer:
$1,200 - $2,350/wk
$8,500/mo
Off Season:
$850 - $1,400/wk
$2,900/mo