Luxurious Compound in The Preserve, Heated Pool with Stone Patio Surround, Outdoor Living & Dining Areas,5 Bedrooms, 5 Baths, Multple Lounge Areas, Spectacular Landscaped Grounds
Thoughtfully designed with exceptional architectural detail and beautifully curated interiors, this vacation home offers an extraordinary retreat for discerning guests. Multiple inviting lounge spaces span two levels, with additional gathering...Read more
Location:
Oak Bluffs
Sleeps:
10
Bedrooms:
5
Baths:
5
Price Range:
$17,500 - $32,000
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$24,500
6
7
8
9
10
11
12
$24,500
13
14
15
16
17
18
19
$24,500
20
21
22
23
24
25
26
$24,500
27
28
29
30
$28,500
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$28,500
4
5
6
7
8
9
10
$30,500
11
12
13
14
15
16
17
$30,500
18
19
20
21
22
23
24
$30,500
25
26
27
28
29
30
31
$30,500
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$32,000
8
9
10
11
12
13
14
$32,000
15
16
17
18
19
20
21
$32,000
22
23
24
25
26
27
28
$30,500
29
30
31
$24,500
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$24,500
5
6
7
8
9
10
11
$24,500
12
13
14
15
16
17
18
$24,500
19
20
21
22
23
24
25
$24,500
26
27
28
29
30
$17,500
Clean Fee:
$950 per week ($350 interim cleaning required on multiple weeks rentals)
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 - $12,500
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
$11,500
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$11,500
4
5
6
7
8
9
10
$11,500
11
12
13
14
15
16
17
$12,500
18
19
20
21
22
23
24
$12,500
25
26
27
28
29
30
31
$12,500
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$17,000
8
9
10
11
12
13
14
$17,000
15
16
17
18
19
20
21
$17,000
22
23
24
25
26
27
28
$12,500
29
30
31
$10,000
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$10,000
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
$6,000
Clean Fee:
$500 per week
Tax: State & Local:
14.45
Owners are also open to weekday arrival and departure to accommodate the need for auto ferry ticket reservations.
Historic 5 Bedroom Home, Newly Updated, Tucked in Historic Center of West Tisbury
Historic Charm in the Heart of Beautiful West Tisbury. This thoughtfully renovated home blends classic character with modern comfort, featuring a beautifully updated kitchen, three stylish baths, and five inviting...Read more
Location:
West Tisbury
Sleeps:
10
Bedrooms:
5
Baths:
3
Price Range:
$3,000 - $11,000
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
$7,750
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$7,750
4
5
6
7
8
9
10
$7,750
11
12
13
14
15
16
17
$7,750
18
19
20
21
22
23
24
$7,750
25
26
27
28
29
30
31
$7,750
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$11,000
8
9
10
11
12
13
14
$11,000
15
16
17
18
19
20
21
$11,000
22
23
24
25
26
27
28
$7,750
29
30
31
$5,500
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$5,500
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
$3,500
Clean Fee:
$500 per week
Tax: State & Local:
11.7
Owners are also open to weekday arrivals and departures to meet the need for auto ferry tickets. Please inquire to discuss!
Charming Saltbox Edgartown Home, Newly Updated , Island Grove Area, 4 Bedroom, 2 bath, Sleeps 7.
Thoughtfully updated contemporary Saltbox-style retreat, tucked away in the desirable Island Grove area of Edgartown. Surrounded by a spacious yard/lawn area & mature plantings, this inviting vacation home offers the perfect blend...Read more
Location:
Edgartown
Sleeps:
7
Bedrooms:
4
Baths:
2
Price Range:
$3,200 - $6,000
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$3,600
6
7
8
9
10
11
12
$3,600
13
14
15
16
17
18
19
$3,600
20
21
22
23
24
25
26
$4,200
27
28
29
30
$5,500
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$5,500
4
5
6
7
8
9
10
$5,800
11
12
13
14
15
16
17
$5,800
18
19
20
21
22
23
24
$6,000
25
26
27
28
29
30
31
$6,000
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$7,700
8
9
10
11
12
13
14
$7,700
15
16
17
18
19
20
21
$7,700
22
23
24
25
26
27
28
$6,900
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
$3,700
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:
$500 per week
Tax: State & Local:
11.7
Owner open to weekday arrival and departure July weeks to accommodate the need for auto ferry tickets.
Stunning New Custom Home, Heated Pool, 20' x 36', 5 Bedrooms, 5 Bath, West Chop Area of Vineyard Haven
Welcome to this exceptional contemporary executive retreat, nestled within a newly developed enclave in the highly sought-after West Chop area of Vineyard Haven. Thoughtfully custom-built and offering nearly 4,200 square...Read more
Location:
Vineyard Haven
Sleeps:
10
Bedrooms:
5
Baths:
5
Price Range:
$18,000 - $30,000
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$18,000
6
7
8
9
10
11
12
$18,000
13
14
15
16
17
18
19
$18,000
20
21
22
23
24
25
26
$20,000
27
28
29
30
$20,000
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$20,000
4
5
6
7
8
9
10
$20,000
11
12
13
14
15
16
17
$25,000
18
19
20
21
22
23
24
$25,000
25
26
27
28
29
30
31
$25,000
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$30,000
8
9
10
11
12
13
14
$30,000
15
16
17
18
19
20
21
$30,000
22
23
24
25
26
27
28
$25,000
29
30
31
$25,000
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$25,000
5
6
7
8
9
10
11
$20,000
12
13
14
15
16
17
18
$20,000
19
20
21
22
23
24
25
$20,000
26
27
28
29
30
$18,000
Clean Fee:
$1000 ($600 interim clean on multiple week rentals)
Tax: State & Local:
11.7
Pool Heated to 82 Degrees, included in Rental Rate July & August.
Pool Heated to 82. Degrees, June, September, Additional Charge $250 per week. May & October weeks additional cost, please inquire!
Beautiful Vineyard Contemporary Farmhouse featuring multiple living spaces, five bedrooms,3 Baths, seamless indoor and outdoor gathering areas. Spacious deck dining & lounge area, wraparound porch, peaceful island setting.
Nestled in the desirable Dodger's Hole community on the outskirts of Edgartown, this beautifully furnished Contemporary Farmhouse offers the perfect Martha's Vineyard retreat for extended families and groups of friends....Read more
Location:
Edgartown
Sleeps:
10
Bedrooms:
5
Baths:
3
Price Range:
$4,500 - $5,000
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:
$750 per week
Tax: State & Local:
11.7
Owner is also open to renting Fri to Fri Dates or other 7 night stays July weeks open to accommodate the need for auto ferry tickets.
Quintessential In-town Vineyard Haven Home, Recently Updated, Walk to all the Village has to offer. Owen Park on the Harbor just Across the Street, Private Yard and Patio, 5 Bedrooms, 4 Baths
Welcome to the Edmond Crowell House, ideally located in the Historic District of Upper Main Street in Vineyard Haven. This is the perfect vacation retreat for those who appreciate the...Read more
Lovely Oak Bluffs Escape, 3 Bedrooms in Main House, 2 Bedrooms over Garage, 3.5 Baths Multiple Living Spaces, Walk to Oak Bluffs Center, 1 Mile
Nestled on a tranquil cul-de-sac in the heart of Oak Bluffs, this meticulously renovated Modern Colonial offers a special Martha's Vineyard experience. Thoughtfully reimagined in 2025, the property encompasses a...Read more
New Gorgeous Contemporary Colonial Home, 4 bedrooms, 4.5 Baths, Sleeps 8, Spacious Yard Area, Deck Dining & Patio Area
Please note exterior photos to follow within 2 weeks. Tucked away on a half-acre at the end of a quiet lane just outside Edgartown, this exquisite coastal contemporary Colonial offers a...Read more
Picture Perfect Newly Updated Edgartown home. Heated Saltwater Pool, Gorgeous Large Yard
Note: Pool is 14 x 30', 3.5 feet to 6 feet deep. Owner offering a 10% discount off the rental rate for the weeks of 7/11, 7/18, 8/23 - 2026,...Read more
Location:
Edgartown
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$13,000 - $15,500
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
$13,500
20
21
22
23
24
25
26
$13,500
27
28
29
30
$13,500
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$13,500
4
5
6
7
8
9
10
$14,000
11
12
13
14
15
16
17
$14,000
18
19
20
21
22
23
24
$14,000
25
26
27
28
29
30
31
$14,500
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$14,500
8
9
10
11
12
13
14
$15,500
15
16
17
18
19
20
21
$15,500
22
23
24
25
26
27
28
$15,500
29
30
31
$15,000
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$15,000
5
6
7
8
9
10
11
$14,000
12
13
14
15
16
17
18
$13,000
19
20
21
22
23
24
25
$13,000
26
27
28
29
30
Clean Fee:
$650 per week
Tax: State & Local:
11.7
Pool Heated to 82 degrees July & August weeks included in the rental rate
Pool Heated to 82 degrees, June & September weeks, additional $300 propane surcharge
Gorgeous Waterfront Home, Stunning Views, Spacious Vacation Home, Perfect for Extended Family & Friends
Note: Exterior photos were taken in the winter. The deck will be set up for summer relaxing and dining, not seen in the current photos. New Sofas for 2026 in the office...Read more
