Owner offering 15% off all remaining weeks open 2026! Victorian East Chop Cottage all Newly updated, 4 Bedrooms, 3.5 Baths, Main House and Detached Guest Suite
Nestled in the highly sought-after East Chop neighborhood of Oak Bluffs, this charming Victorian cottage offers the perfect blend of classic Vineyard character and modern comfort. Ideally located within walking...Read more
Location:
Oak Bluffs
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$3,800 - $15,170
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$6,800
6
7
8
9
10
11
12
$6,800
13
14
15
16
17
18
19
$6,800
20
21
22
23
24
25
26
$6,800
27
28
29
30
$6,800
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$6,800
4
5
6
7
8
9
10
$11,050
11
12
13
14
15
16
17
$11,050
18
19
20
21
22
23
24
$11,050
25
26
27
28
29
30
31
$11,050
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$15,170
8
9
10
11
12
13
14
$15,170
15
16
17
18
19
20
21
$15,170
22
23
24
25
26
27
28
$15,170
29
30
31
$5,950
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$5,950
5
6
7
8
9
10
11
$5,950
12
13
14
15
16
17
18
$5,950
19
20
21
22
23
24
25
$5,950
26
27
28
29
30
$5,950
Clean Fee:
$500 per week
Tax: State & Local:
11.7
Owners are also open to weekday arrival and departure to accommodate the need for auto ferry ticket reservations.
Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.
Visitors will enjoy this delightful & comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs.
Relax in the breeze with your morning coffee on the front...Read more
Edgartown Retreat-Impeccably Maintained, Heated Pool -14 x 32', Screened Porch, Bluestone Patio, Exqusite Grounds and Gardens, Multiple Interior and Exterior Living Spaces
Nestled amidst picturesque grounds and gardens, this enchanting vacation getaway boasts an array of indoor and outdoor spaces seamlessly interconnected. The focal points of summer relaxation include a 14 x...Read more
Location:
Edgartown
Sleeps:
8
Bedrooms:
4
Baths:
2
Price Range:
$8,000 - $15,000
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
$12,000
27
28
29
30
$15,000
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$15,000
4
5
6
7
8
9
10
$15,000
11
12
13
14
15
16
17
$15,000
18
19
20
21
22
23
24
$15,000
25
26
27
28
29
30
31
$15,000
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$15,000
8
9
10
11
12
13
14
$15,000
15
16
17
18
19
20
21
$15,000
22
23
24
25
26
27
28
$11,000
29
30
31
$8,000
September 2027
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
19
20
21
22
23
24
25
26
27
28
29
30
Clean Fee:
$400 per week
Tax: State & Local:
11.7
Pool Heated to 81 degrees included in rental rate July & August weeks.
Pool Heat shoulder season weeks additional propane surcharge, please inquire!
Summer Compound in a majestic location. Vintage vacation home perfect for large family gatherings. Enjoy sweeping ocean views from the large comfortably furnished veranda. A large screened porch offers seating...Read more
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths
This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more
Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,
Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more
Location:
Oak Bluffs
Sleeps:
6
Bedrooms:
3
Baths:
2
Price Range:
$3,500 - $7,500
June 2027
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
$4,000
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$4,000
4
5
6
7
8
9
10
$5,000
11
12
13
14
15
16
17
$4,500
18
19
20
21
22
23
24
$4,500
25
26
27
28
29
30
31
$5,000
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$7,500
8
9
10
11
12
13
14
$7,500
15
16
17
18
19
20
21
$7,500
22
23
24
25
26
27
28
$7,500
29
30
31
$4,500
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$4,500
5
6
7
8
9
10
11
$4,500
12
13
14
15
16
17
18
$3,500
19
20
21
22
23
24
25
$3,500
26
27
28
29
30
$3,500
Clean Fee:
$350 ($275 for interim cleaning on multiple week rentals)
Charming Newly Updated Menemsha Cottage, 2 + Bedroom Cottage Sleeps 5, AC, Screened Porch & Deck, Walk to Menemsha Village & Beach
Dreaming of Vacationing in an idyllic Menemsha Cottage? This adorable newly updated 1950s cottage nestled in the village area provides easy access to numerous exclusive Chilmark beaches with town permits and Menemsha Beach...Read more
Location:
Chilmark
Sleeps:
5
Bedrooms:
3
Baths:
1
Price Range:
$3,200 - $3,200
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
Clean Fee:
$325 per week
Tax: State & Local:
11.7
Owner will rent off weekend arrival and departure dates, weeks open in 2026, to accommodate the need for Auto ferry reservations. Inquire!
LIGHT FILLED CONTEMPORARY HOME, AC, DECK AND SUN PORCH, SLEEPS 8
Set on a quiet circular street (Teaberry Lane), on the outskirts of Edgartown. Bike paths at the end of the street connect to town and miles of touring trails. This...Read more
Lovely Home in Island Grove Area of Edgartown Conveniently Located between South Beach and Edgartown Village. Association Tennis Courts and Pickleball Available to Renters
This recently updated home is tucked in the Island Grove area of Edgartown and is a perfect retreat for families & friends to gather. Located in a desirable neighborhood with access...Read more
