Adorable Oak Bluffs Cottage Just Over a Mile to the Village Center and Town Beaches, Porch, Deck, 4 Bedrooms, 2 Baths
Nestled on a quiet street, this recently updated residence boasts delightful indoor and outdoor living areas. The entrance porch offers cozy seating with wicker chairs and a small dining table that...Read more
Lovely contemporary home in one of the island's premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches....Read more
SPACIOUS LIGHTFILLED 3 BEDROOM, 3 BATH HOME, PRIVATE DECK WITH PATIO DINING, 7 MINUTE DRIVE TO THE CENTER OF OAK BLUFFS AND INKWELL BEACH
Experience the best of Island living—peaceful residential surroundings, the vibrant shops and attractions of the three Down Island towns (Oak Bluffs, Edgartown, and Vineyard Haven), and quick access to public...Read more
SWEET 3-BEDROOM, 3-BATH CHILMARK COTTAGE, SPACIOUS SCREENED PORCH AND DECK AREAS, OUTDOOR SHOWER; PRIVATE LOCATION ON 4 ACRES, 10 MINUTES TO LUCY VINCENT AND LONG POINT BEACHES
Charming updated summer home features a dining room that seats six, well-stocked kitchen, living room, plus screen porch with ceiling fan, dining table and chairs for 8, and reading/lounging nooks, leading...Read more
Location:
Chilmark
Sleeps:
6
Bedrooms:
3
Baths:
3
Price Range:
$3,300 - $4,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$3,300
7
8
9
10
11
12
13
$3,300
14
15
16
17
18
19
20
$3,300
21
22
23
24
25
26
27
$3,900
28
29
30
$3,900
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$3,900
5
6
7
8
9
10
11
$3,900
12
13
14
15
16
17
18
$3,900
19
20
21
22
23
24
25
$3,900
26
27
28
29
30
31
$4,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$4,000
2
3
4
5
6
7
8
$4,000
9
10
11
12
13
14
15
$4,000
16
17
18
19
20
21
22
$4,000
23
24
25
26
27
28
29
$4,000
30
31
$4,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$3,300
20
21
22
23
24
25
26
$3,300
27
28
29
30
$3,300
Clean Fee:
$400 per week, $150 interim cleaning on multiple week rentals
Country Charm, Screened Porch, Large Yard, Bike Paths
Large families enjoy this wonderful summer home. Conveniently located close to West Tisbury town center. Great summer spaces for relaxing and enjoying barbeques, lawn games, lunch on the screened porch,...Read more
Location:
West Tisbury
Sleeps:
10
Bedrooms:
5
Baths:
3
Price Range:
$3,600 - $4,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$3,600
7
8
9
10
11
12
13
$3,600
14
15
16
17
18
19
20
$3,600
21
22
23
24
25
26
27
$3,800
28
29
30
$4,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$4,000
5
6
7
8
9
10
11
$4,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
31
$4,800
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$4,800
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
$4,800
23
24
25
26
27
28
29
30
31
$3,900
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$3,900
6
7
8
9
10
11
12
$3,900
13
14
15
16
17
18
19
$3,900
20
21
22
23
24
25
26
$3,900
27
28
29
30
$3,900
Clean Fee:
$500 per week
Tax: State & Local:
11.7
Ferry Ticket available 7/12 - 7/19 - please inquire
North Slope Hilltop House. Private yard, Screeened Porch and Patio, 8 minute drive to Lucy Vincent Beach or Menemsha Village
Delightful, 3 bedroom, 2 bath home with AC. Private Chilmark hilltop location! This sweet home features an open kitchen, living, and dining area, and a screened porch for your summer...Read more
New cape style home, glistening with attention to detail! Not all homes have to be large to feature quality, luxury decor. This is a custom-built cape, where the owners have...Read more
Classic Lovely Vineyard Cottage, Approximately 1.5 Miles to Oak Bluffs Center and Beaches. Mature Landscaped Yard, Spacious Deck
The Perfect Cozy Cottage, is pristinely maintained and situated in a quiet neighborhood just on the outskirts of Oak Bluffs. This spacious 2 bedroom, 2 bath home sleeps 4. The...Read more
Location:
Oak Bluffs
Sleeps:
4
Bedrooms:
2
Baths:
2
Price Range:
$2,700 - $4,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$2,700
7
8
9
10
11
12
13
$2,700
14
15
16
17
18
19
20
$2,700
21
22
23
24
25
26
27
$2,700
28
29
30
$3,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$3,500
5
6
7
8
9
10
11
$3,500
12
13
14
15
16
17
18
$3,500
19
20
21
22
23
24
25
$3,500
26
27
28
29
30
31
$4,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$4,000
2
3
4
5
6
7
8
$4,000
9
10
11
12
13
14
15
$4,000
16
17
18
19
20
21
22
$4,000
23
24
25
26
27
28
29
$4,000
30
31
$3,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$2,700
13
14
15
16
17
18
19
$2,700
20
21
22
23
24
25
26
$2,700
27
28
29
30
Clean Fee:
$300, additional may apply multiple week rentals
Tax: State & Local:
11.7
Owner will rent off weekend dates, with a 7-night minimum, to accommodate the need for auto ticket reservations.
Lovely, Recently Updated West Chop Area Home, Spacious Deck, Open Living Spaces, 15 Minute Walk to Town
This lovely, spacious, airy home was recently renovated, an open-concept home filled with natural light and located on a private road. Your next “home away from home” is perfectly located minutes from all...Read more
Location:
Vineyard Haven
Sleeps:
6
Bedrooms:
3
Baths:
2
Price Range:
$3,500 - $4,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$3,800
28
29
30
$4,300
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$4,300
5
6
7
8
9
10
11
$4,300
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
31
$5,500
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$5,500
2
3
4
5
6
7
8
$4,500
9
10
11
12
13
14
15
$5,800
16
17
18
19
20
21
22
$4,800
23
24
25
26
27
28
29
$4,000
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
$3,500
Clean Fee:
$450 per week
Tax: State & Local:
11.7
Rates reduced for available weeks in July & August - see calendar for adjusted rates
Lovely Cape Home, Newly Updated, Private Back Deck with Outdoor Dining & Grill, 3 Bedrooms w/AC and TV, 1.5 baths
Nestled on a serene lane in the outskirts of Vineyard Haven, this newly updated & charming Cape Style residence exudes chic charm. Step inside to discover an inviting open layout...Read more
Meetinghouse Middle Condo, Association Pool, Central Air
Set in quiet Meeting House Village on the outskirts of Edgartown, this lovely condominium unit features a spacious open main living level with glass sliders leading out to the deck with a...Read more
The Sweetest In-town Cottage! 2 Minute Walk to Main St
This adorable cottage-style home features 2 bedrooms, and 2 baths and is tucked in on a tiny side street off of Main St. Walk to all that the village center...Read more
Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association Tennis Courts, AC, Wi-fi, Bike Paths Nearby
MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home tucked away on the shores of Sengekontacket Lagoon in a community of homes - featuring gorgeous views, mini-split AC units in main living areas,...Read more
Location:
Oak Bluffs
Sleeps:
6
Bedrooms:
4
Baths:
2
Price Range:
$3,600 - $3,700
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$3,600
7
8
9
10
11
12
13
$3,600
14
15
16
17
18
19
20
$3,600
21
22
23
24
25
26
27
28
29
30
$3,700
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$3,700
5
6
7
8
9
10
11
$4,100
12
13
14
15
16
17
18
$3,700
19
20
21
22
23
24
25
$3,700
26
27
28
29
30
31
$3,700
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$3,700
2
3
4
5
6
7
8
$4,100
9
10
11
12
13
14
15
$4,100
16
17
18
19
20
21
22
$4,100
23
24
25
26
27
28
29
$3,910
30
31
$3,660
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$3,660
6
7
8
9
10
11
12
$3,660
13
14
15
16
17
18
19
$3,660
20
21
22
23
24
25
26
$2,460
27
28
29
30
$2,460
Clean Fee:
$475 per week
Tax: State & Local:
11.7
Owner just reduced rates for available weeks in July - see calendar for adjusted rates
Owner will rent weekday to weekday the middle two weeks of July with a 7 night minimum to accommodate the need for auto ferry tickets if none available the weekend dates.
Newly updated vacation retreat, 3 minute walk to association pool, 10 min drive to Lamberts Cove Beach or South Shore Beach
This lovely West Tisbury contemporary cape features multiple living spaces both indoors and out for your vacation enjoyment. Just a 3-minute walk from the house to the association pool! This home...Read more
