Menemsha Waterfront, Magnificent Views and Private Location, WiFi
This quintessential Chilmark cottage/home has been impeccably maintained, The dining and living areas with spectacular views across Menemsha Channel to Aquinnah open to a wrap-around deck. Enjoy spectacular water views...Read more
Location:
Chilmark
Sleeps:
6
Bedrooms:
3
Baths:
2
Price Range:
$4,000 - $8,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$8,000
28
29
30
$8,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$8,000
5
6
7
8
9
10
11
$8,000
12
13
14
15
16
17
18
$8,000
19
20
21
22
23
24
25
$8,000
26
27
28
29
30
31
$8,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$8,000
2
3
4
5
6
7
8
$8,000
9
10
11
12
13
14
15
$8,000
16
17
18
19
20
21
22
$8,000
23
24
25
26
27
28
29
$8,000
30
31
$6,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
$4,000
Clean Fee:
$375 per week, owner will provide sheets, towels, beach towels, additional $225 per rental period
Tax: State & Local:
11.7
Owner will provide, sheets, towels & beach towels for an additional $225 per rented period.
Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bedrooms, 15 Minute Walk to Oak Bluffs Center and Inkwell Beach
All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, all just a...Read more
The Boathouse, East Chop Location, Gorgeous Water and Sunset Views, Architect Designed Gem
Designed by a renowned island architect and custom-crafted, The Boathouse underwent construction and total renovation in 2016 and is now a terrific year-round home. The exterior of the house maintains...Read more
Gracious Village Area 5 Bedroom Home, Light Filled Interior, Mulitple Living Spaces, Large Landscaped Yard, Located on Quiet Side St, 5 min Walk to Main St.
Stunning Edgartown Village Home! This meticulously maintained and newly updated property offers multiple living areas, 5 bedrooms, and 3.5 baths, surrounded by a lushly landscaped yard. Just a 5-minute walk...Read more
Summer Wind in the Heart of Oak Bluffs, Water views. 2 minute Walk to Inkwell Beach & 5 minute walk to town, All Newly Remodeled 5 Bedroom, 3 Bath Home With Deluxe Amenities
Set in the heart of Oak Bluffs center, this newly renovated home features water views, walk to Inkwell Beach and Pay Beach and walk to the town center all within...Read more
Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC
This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more
Location:
Oak Bluffs
Sleeps:
6
Bedrooms:
3
Baths:
2
Price Range:
$3,500 - $8,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
$6,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$6,500
5
6
7
8
9
10
11
$7,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
31
$7,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$7,000
2
3
4
5
6
7
8
$8,000
9
10
11
12
13
14
15
$8,000
16
17
18
19
20
21
22
$8,000
23
24
25
26
27
28
29
$8,000
30
31
$3,500
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
Clean Fee:
$400 per week
Tax: State & Local:
11.7
Ferry Tickets Available 6/27-7/4, 7/4-7/11, 7/11-7/18, 7/18-7/25 - please inquire
Note: Owner maintains security camera on front of house
East Chop Classic Waterfront Home, Private Dock, Mooring Available, Spectacular Sunsets
Experience the epitome of summer living at East Chop Oak Bluffs in this delightful waterfront retreat. Nestled amidst the serenity of the beachfront, this cozy home boasts a private dock...Read more
WATER VIEW, IN TOWN - 2 MINUTE WALK TO MAIN ST, WIFI, A/C
In-Town Luxury Home. This state-of-the-art home features a large living room with a dining area and a gourmet kitchen with Viking and Sub Zero appliances. Each of the 4 bedrooms...Read more
Perfect Retreat for Large Families, 1.5 miles to Oak Bluffs Town Center & Beach, Bike Path at end of Street
Spacious and perfect for extended families, featuring multiple attractively furnished living areas, and sleeps 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with...Read more
Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas
Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more
Beautiful Oak Bluffs home just blocks from the Center of Town, Ocean Park and Inkwell Beach.
Note: the kitchen is being completely remodeled for summer 2024 and will have all new high-end appliances, Subzero, Thermador, and new cabinets, and counters.
Gorgeous Water views, set in private Mink Meadows Golf Course Community , Private Association Beach, Walk or drive to the Golf Course Club House
Beautiful home in Mink Meadows area of West Chop. Guests will enjoy the gorgeous water views across Mink Meadows Pond to the North Shore. Swans, geese, and ducks reside in the...Read more
Water view Upper Makonikey Home, Distinctive Design by Royal Barry Wills, Two Private Association Beaches, Central A/C
Classic Royal Barry Wills-designed cedar-shingled Vineyard home, beautifully sited on five private landscaped acres in the exclusive enclave of homes known as Makonikey. Lovely distant water views of Vineyard Sound and...Read more
Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully Landscaped
Outstanding vacation home, centrally located to all three down-island town centers and multiple public beaches. This lovely home in a serene setting overlooks the picturesque Little Duarte Pond in the Iron Hill...Read more
The Retreat at Towanticut Where Coastal Elegance Meets Island Serenity, 3 Bedrooms, 2 Baths, Landscaped Yard, Deck Dining Area
Welcome to The Retreat at Towanticut— a chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just a 15-minute stroll to Circuit Avenue...Read more
