Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis
Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more
Mink Meadows Family Compound, Private Heated Pool, Walk or Drive to Private Association Beach, Beautifully Landscaped Yard, Deck and Patio, Golf 1 Mile from House
Spacious 4 Bedroom, 3.5 bath family compound with 28 x 14 heated pool, multiple indoor/outdoor living spaces situated in Mink Meadows Association.
Mink Meadows Public Golf Course is just a short drive...Read more
Location:
Vineyard Haven
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$4,400 - $8,500
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$4,400
7
8
9
10
11
12
13
$4,400
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
$7,800
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$7,800
5
6
7
8
9
10
11
$7,800
12
13
14
15
16
17
18
$7,800
19
20
21
22
23
24
25
$7,800
26
27
28
29
30
31
$8,500
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$8,500
2
3
4
5
6
7
8
$8,500
9
10
11
12
13
14
15
$8,500
16
17
18
19
20
21
22
$8,500
23
24
25
26
27
28
29
$8,500
30
31
$6,500
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
$6,500
Clean Fee:
$550 per week
Tax: State & Local:
11.7
Pool heated to 81 degrees in July & August included in rental rate.
Pool heated to 81 degrees June & September additional $250 per week. Requests for higher temperature, please contact your agent for details.
Pool heated to 81 degrees May & October additional $350 per week. Requests for higher temperature, please contact your agent for details.
Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths
Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more
Outer Harbor Waterfront, West Chop Area, Private Sandy Beach, Lush Gardens and Large Yard, Magnificent Water Views
NOTE: New upgrades for 2026 Rental Season: Mini Split AC units in the Living Area, Kitchen, and Bedrooms, New Sofa in the Living Area, Newly Painted, All new Windows throughout the House....Read more
Sophisticated New Contemporary Home, Walk to Lambert's Cove Beach, Multiple Indoor Outdoor Living Spaces, Privately Tucked in Longview Area of West Tisbury
Discover a captivating modern retreat in the heart of West Tisbury on Martha’s Vineyard. Newly built and thoughtfully designed, this striking home blends clean architectural lines with contemporary comfort, offering...Read more
Location:
West Tisbury
Sleeps:
7
Bedrooms:
3
Baths:
3
Price Range:
$4,000 - $8,500
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$7,000
28
29
30
$8,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$8,500
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$8,500
19
20
21
22
23
24
25
$8,500
26
27
28
29
30
31
$8,500
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$8,500
2
3
4
5
6
7
8
$10,500
9
10
11
12
13
14
15
$12,500
16
17
18
19
20
21
22
$12,500
23
24
25
26
27
28
29
$10,500
30
31
$10,500
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$10,500
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
$7,000
Clean Fee:
$600 per week
Tax: State & Local:
11.7
Ferry tickets available for purchase, 7/5-7/12, 7/12-7/19, 7/19-7/26, & 7/26-8/2 - please inquire (mv)
Lovely Custom Contemporary Home, Tucked in the Community of Bayes Hill, 4 Bedrooms, 4 Bath, Landscaped, Deck, Patio Dining Area
Designed with a sophisticated contemporary aesthetic, this chic vacation retreat showcases an open floor plan, expansive windows, and beautifully curated interiors. Offering four bedrooms and 3.5 baths, the home is...Read more
Location:
Oak Bluffs
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$7,000 - $8,050
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$7,500
7
8
9
10
11
12
13
$7,500
14
15
16
17
18
19
20
$7,500
21
22
23
24
25
26
27
$7,500
28
29
30
$7,750
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$7,750
5
6
7
8
9
10
11
$7,750
12
13
14
15
16
17
18
$7,750
19
20
21
22
23
24
25
$7,750
26
27
28
29
30
31
$8,050
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$8,050
2
3
4
5
6
7
8
$8,050
9
10
11
12
13
14
15
$8,050
16
17
18
19
20
21
22
$8,050
23
24
25
26
27
28
29
$8,050
30
31
$8,050
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$8,050
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
$7,500
Clean Fee:
$500 per week
Tax: State & Local:
11.7
Auto Ferry Ticket available for Purchase 7/19 - 7/26. Please inquire! (mv)
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
$8,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
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.
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
Location:
Oak Bluffs
Sleeps:
10
Bedrooms:
5
Baths:
3
Price Range:
$8,000 - $8,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$8,000
7
8
9
10
11
12
13
14
15
16
17
18
19
20
$9,000
21
22
23
24
25
26
27
$10,000
28
29
30
$12,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$12,000
5
6
7
8
9
10
11
$12,000
12
13
14
15
16
17
18
$13,000
19
20
21
22
23
24
25
$14,000
26
27
28
29
30
31
$14,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$14,000
2
3
4
5
6
7
8
$19,000
9
10
11
12
13
14
15
$19,000
16
17
18
19
20
21
22
$19,000
23
24
25
26
27
28
29
$12,000
30
31
$9,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$9,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
27
28
29
30
Clean Fee:
$550
Tax: State & Local:
11.7
Ferry tickets available for purchase, 7/26 - 8/2 Please inquire (mv)
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, 7/18-7/25 - please inquire
Note: Owner maintains security camera on front of house
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 - $8,000
June 2026
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
27
$12,000
28
29
30
$15,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$15,000
5
6
7
8
9
10
11
$15,000
12
13
14
15
16
17
18
$15,000
19
20
21
22
23
24
25
$15,000
26
27
28
29
30
31
$15,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$15,000
2
3
4
5
6
7
8
$15,000
9
10
11
12
13
14
15
$15,000
16
17
18
19
20
21
22
$15,000
23
24
25
26
27
28
29
$11,000
30
31
$8,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$8,000
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:
$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!
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
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
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
Location:
Vineyard Haven
Sleeps:
8
Bedrooms:
5
Baths:
4
Price Range:
$4,370 - $7,900
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$5,500
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
$7,900
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$7,900
5
6
7
8
9
10
11
$7,900
12
13
14
15
16
17
18
$7,900
19
20
21
22
23
24
25
$7,900
26
27
28
29
30
31
$7,900
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$7,900
2
3
4
5
6
7
8
$7,900
9
10
11
12
13
14
15
$7,900
16
17
18
19
20
21
22
$7,900
23
24
25
26
27
28
29
$7,900
30
31
$4,370
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$4,370
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
$4,500
Clean Fee:
$500 per week
Tax: State & Local:
11.7
Ferry Tickets Available for Purchase, 7/19 - 26. Inquire for Details (mv)
Lovely 6 Bedroom Home in Heart of Katama, Multiple Living Spaces, Perfect for Extended Families, 8/10ths mile to South Beach
Ideally situated in the heart of the Katama area of Edgartown, 8/10 of a mile from South Beach, this lovely expanded Cape-style home is perfectly designed for extended families and friends....Read more
Location:
Katama
Sleeps:
11
Bedrooms:
6
Baths:
3
Price Range:
$4,150 - $7,850
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$4,450
7
8
9
10
11
12
13
$4,450
14
15
16
17
18
19
20
$4,450
21
22
23
24
25
26
27
$6,000
28
29
30
$10,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$10,000
5
6
7
8
9
10
11
$10,000
12
13
14
15
16
17
18
$12,500
19
20
21
22
23
24
25
$12,500
26
27
28
29
30
31
$12,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$12,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$12,000
16
17
18
19
20
21
22
$12,000
23
24
25
26
27
28
29
$12,500
30
31
$7,850
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$7,850
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
$6,500
Clean Fee:
$550 per week
Tax: State & Local:
11.7
Ferry ticket available for purchase 7/12 - 7/19 - Please Inquire (mv)
