Vineyard Haven Vacation Rentals

Vineyard Haven, Martha’s Vineyard’s primary port town, is the perfect place for vacation rental guests who want to be close the action. While staying in a Vineyard Haven vacation rental, you have direct access to the waterfront and Vineyard Haven’s many fun events, world-famous restaurants, and classic bars. Vacations in Vineyard Haven are full of excitement and fun on the water, and going out in Vineyard Haven after a day at the beach gives you the classic Martha’s Vineyard experience.

 

 

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Luxurious Home, Privately Situated in the West Chop Area of Vineyard Haven, Heated Pool, North Shore Waterviews, Multiple Indoor/Outdoor LIving Spaces. 6 Bedrooms, 5.5 Baths Sleeps 13.

Exceptional Rental Offering: Stunning 6-Bedroom, 5.5-Bath Home in West Chop, Vineyard Haven

Experience the epitome of summer luxury living in this exquisite 6-bedroom, 5.5-bath home nestled in the desirable West...Read more

Location: 
Vineyard Haven
Sleeps: 
13
Bedrooms: 
6
Baths: 
5
Price Range:
$14,000 - $35,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
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4
5
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10
11
12
13
14
15
16
17
18
19
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22
23
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25
26
27
28
29
30
 $25,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$25,000
5
6
7
8
9
10
11
$25,000
12
13
14
15
16
17
18
$30,000
19
20
21
22
23
24
25
$30,000
26
27
28
29
30
31
 $35,000
August 2026
SuMoTuWeThFrSaWeek
 1
$35,000
2
3
4
5
6
7
8
$35,000
9
10
11
12
13
14
15
$35,000
16
17
18
19
20
21
22
$35,000
23
24
25
26
27
28
29
$35,000
30
31
 $25,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$25,000
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
$16,000
27
28
29
30
 $14,000
Clean Fee: 
$2000 per week
Tax: State & Local: 
11.7
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HODGE

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Property Details
Stunning Waterfront Home on the Lagoon, Complete Renovation and Professionally Decorated. Private Beach Area and Dock, Perfect Retreat for Extended Families, Walk to Town. Swim, Sun, Kayak or Bring your own boat.

Exquisite waterfront family compound sleeps 12, with 270-degree water view of the Lagoon,  85' of sandy beach on the lagoon, and a private dock for boaters. Private dock (12' draft) with mooring and private sandy...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
6
Baths: 
4
Price Range:
$8,500 - $25,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$14,000
7
8
9
10
11
12
13
$14,000
14
15
16
17
18
19
20
$14,000
21
22
23
24
25
26
27
$14,000
28
29
30
 $19,250
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$19,250
5
6
7
8
9
10
11
$19,250
12
13
14
15
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17
18
$19,250
19
20
21
22
23
24
25
$22,500
26
27
28
29
30
31
 $25,000
August 2026
SuMoTuWeThFrSaWeek
 1
$25,000
2
3
4
5
6
7
8
$25,000
9
10
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12
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14
15
$25,000
16
17
18
19
20
21
22
$25,000
23
24
25
26
27
28
29
$22,000
30
31
 $14,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
$14,000
6
7
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9
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$12,000
13
14
15
16
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18
19
$11,000
20
21
22
23
24
25
26
$11,000
27
28
29
30
 $11,000
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

 

Private Dock plus Mooring that draws 12 feet. If you plan to bring a boat please speak with the agent for details as must be approved by owner!

 

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MONLC

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Property Details

Gorgeous estate home on large acreage, gorgeous water views with the ferry passing to and from the Vineyard, heated pool with patio surround, and an outdoor kitchen and patio dining...Read more

Location: 
Vineyard Haven
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$7,000 - $20,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$10,000
7
8
9
10
11
12
13
$10,000
14
15
16
17
18
19
20
$10,000
21
22
23
24
25
26
27
$16,500
28
29
30
 $16,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$16,750
5
6
7
8
9
10
11
$16,750
12
13
14
15
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17
18
$16,750
19
20
21
22
23
24
25
$18,500
26
27
28
29
30
31
 $20,500
August 2026
SuMoTuWeThFrSaWeek
 1
$20,500
2
3
4
5
6
7
8
$20,500
9
10
11
12
13
14
15
$20,500
16
17
18
19
20
21
22
$18,500
23
24
25
26
27
28
29
$16,000
30
31
 $10,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
$10,000
6
7
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9
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12
$8,000
13
14
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19
$8,000
20
21
22
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$8,000
27
28
29
30
 $7,000
Clean Fee: 
$900 per week
Tax: State & Local: 
11.7

Pool Heated to 82 included in rental rate July & August weeks. 

 

June & September weeks heated to 81 degrees additional $300 propane surcharge per week.

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COS67

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Property Details
Beautiful 3 Bedroom, 3.5 bath Home, Bluestone Patio with Outdoor Dining & Grill , Lovely Landscaped Yard. Situated on Quiet Street, Walk to Town
Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
3
Price Range:
$7,000 - $20,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,500
7
8
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10
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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
 $9,990
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,990
5
6
7
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9
10
11
$9,990
12
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$9,990
19
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21
22
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24
25
$9,990
26
27
28
29
30
31
 $9,990
August 2026
SuMoTuWeThFrSaWeek
 1
$9,990
2
3
4
5
6
7
8
$20,000
9
10
11
12
13
14
15
$20,000
16
17
18
19
20
21
22
$20,000
23
24
25
26
27
28
29
$20,000
30
31
 $9,990
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,990
6
7
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9
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11
12
$7,000
13
14
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19
$7,000
20
21
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26
$7,000
27
28
29
30
 $7,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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THOHP

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Property Details
Exquisite New Contemporary Waterfront Home, Multiple Indoor& Outdoor Living Spaces with Waterviews.

This stunning luxury waterfront home, nestled on the Lagoon, offers breathtaking water views from every corner of the newly built residence. Enjoy the seamless transition between indoor and outdoor living...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
4
Price Range:
$12,500 - $20,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$12,500
7
8
9
10
11
12
13
$14,000
14
15
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17
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19
20
$14,000
21
22
23
24
25
26
27
$14,000
28
29
30
 $16,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$16,000
5
6
7
8
9
10
11
$18,000
12
13
14
15
16
17
18
$18,000
19
20
21
22
23
24
25
$18,000
26
27
28
29
30
31
 $18,000
August 2026
SuMoTuWeThFrSaWeek
 1
$18,000
2
3
4
5
6
7
8
$20,000
9
10
11
12
13
14
15
$20,000
16
17
18
19
20
21
22
$20,000
23
24
25
26
27
28
29
$18,000
30
31
 $18,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$18,000
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$16,000
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner requires two week minimum booking during months July & August

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TAVAM

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Property Details
Outstanding, Newly Updated Vacation Retreat, Heated Saltwater Pool. Multiple Living Spaces, All New Kitchen, Gorgeous Yard, Set in Quiet, Lovely Commmunity of Homes, Stonegate

Impeccable Vacation Getaway with Updated Amenities and a Heated Saltwater Pool

Nestled within the serene community of Stonegate, this exceptional retreat offers a rejuvenating escape. Conveniently located just a brief...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $16,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$11,000
7
8
9
10
11
12
13
$11,000
14
15
16
17
18
19
20
$11,000
21
22
23
24
25
26
27
$11,000
28
29
30
 $13,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$13,000
5
6
7
8
9
10
11
$13,000
12
13
14
15
16
17
18
$13,000
19
20
21
22
23
24
25
$13,000
26
27
28
29
30
31
 $16,000
August 2026
SuMoTuWeThFrSaWeek
 1
$16,000
2
3
4
5
6
7
8
$16,000
9
10
11
12
13
14
15
$16,000
16
17
18
19
20
21
22
$16,000
23
24
25
26
27
28
29
$16,000
30
31
 $11,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,000
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$8,000
20
21
22
23
24
25
26
$8,000
27
28
29
30
 $8,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Pool heated to 82 July & August included in rental rate.  

Spa area in the pool is heated to the same temperature as the pool and is not available Spa jets are also not available for renter use. 

 

Pool heated to 82 June & September when weeks are available additional $300 per week propane surcharge.

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WIL14

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Property Details

Classic updated 7 bedrooms, 5 bath West Chop Home. Nestled on a large landscaped lot on Hatch Rd in Vineyard Haven this spacious home offers the best in vacation home...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
7
Baths: 
5
Price Range:
$5,500 - $15,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$10,000
7
8
9
10
11
12
13
$10,000
14
15
16
17
18
19
20
$10,000
21
22
23
24
25
26
27
$13,000
28
29
30
 $15,000
July 2026
SuMoTuWeThFrSaWeek
 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
SuMoTuWeThFrSaWeek
 1
$15,000
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
 $8,400
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,400
6
7
8
9
10
11
12
$11,000
13
14
15
16
17
18
19
$11,000
20
21
22
23
24
25
26
$11,000
27
28
29
30
 $10,000
Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7
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BAYLM

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Property Details
Spectacular Waterfront Views in exclusive Makonikey area, Ocean Views and Breathtaking Sunsets, Private Beach, Private Location

This serene waterfront retreat offers sweeping water views in an exceptionally private setting, yet is just a 10-minute drive from town, with access to fine dining, shopping, galleries, and entertainment....Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$70 - $12,500
June 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
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28
29
30
 
July 2026
SuMoTuWeThFrSa
 1
2
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9
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25
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$12,500
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
$12,500
30
31
 
September 2026
SuMoTuWeThFrSa
 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: 
$550 per week
Tax: State & Local: 
11.7
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SHAJO

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Property Details

Step into this exquisite Victorian-style residence, meticulously renovated to preserve its original allure while offering a sanctuary away from the bustle of everyday life. Nestled in the picturesque town of...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,000 - $12,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$7,000
28
29
30
 $9,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,000
5
6
7
8
9
10
11
$9,000
12
13
14
15
16
17
18
$9,000
19
20
21
22
23
24
25
$12,000
26
27
28
29
30
31
 $12,000
August 2026
SuMoTuWeThFrSaWeek
 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
$10,000
30
31
 $6,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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SAGID

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Property Details
Newly refurbished Tri Level, Gorgeous Water Views of North Shore in Exclusive Makonikey Area

Stunning Hilltop Post & Beam Vacation Home with a relaxed coastal ambiance and picturesque distant water vistas! Nestled off Lambert’s Cove Rd in Vineyard Haven, this exquisite property resides within...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $11,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,800
7
8
9
10
11
12
13
$5,800
14
15
16
17
18
19
20
$6,800
21
22
23
24
25
26
27
$8,990
28
29
30
 $11,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
5
6
7
8
9
10
11
$11,000
12
13
14
15
16
17
18
$11,000
19
20
21
22
23
24
25
$12,000
26
27
28
29
30
31
 $12,000
August 2026
SuMoTuWeThFrSaWeek
 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
$10,000
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
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
$6,500
27
28
29
30
 $5,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

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CLE20

(0)Inquire/Share
Property Details
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

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$4,500 - $10,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,700
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
$8,100
28
29
30
 $8,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
6
7
8
9
10
11
$9,000
12
13
14
15
16
17
18
$9,000
19
20
21
22
23
24
25
$9,500
26
27
28
29
30
31
 $10,000
August 2026
SuMoTuWeThFrSaWeek
 1
$10,000
2
3
4
5
6
7
8
$10,500
9
10
11
12
13
14
15
$10,500
16
17
18
19
20
21
22
$10,500
23
24
25
26
27
28
29
$10,000
30
31
 $6,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
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
$5,500
27
28
29
30
 $4,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BELJA

(0)Inquire/Share
Property Details
Captain Swain House, Elegant Main & Guest House, 5 Bedrooms, 4.5 Baths, Multiple Indoor/Outdoor Living Spaces, 5 Minute Walk to Town, Expansive Landscaped Yard

In-Town Vacation Retreat in the William Street Historic District
Just a five-minute walk to the heart of town, this spacious and beautifully updated home blends modern comfort with timeless...Read more

Location: 
Vineyard Haven
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$5,000 - $10,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,500
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
$6,000
28
29
30
 $8,500
July 2026
SuMoTuWeThFrSaWeek
 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
SuMoTuWeThFrSaWeek
 1
$8,500
2
3
4
5
6
7
8
$10,000
9
10
11
12
13
14
15
$10,000
16
17
18
19
20
21
22
$10,000
23
24
25
26
27
28
29
$10,000
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
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
 $6,000
Clean Fee: 
$875 per week
Tax: State & Local: 
11.7
Add Favorite
kerr413-01-exterior.jpg
 
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KERR4

(0)Inquire/Share
Property Details
Sophisticated & Charming Waterfront Cottage, Large Waterfront Deck, Dock, Tennis Court, Spectacular Views

Stunning cottage style home where the wate front is literally at your doorstep. Lake Tashmoo is a large saltwater inlet great for swimming, sailing, and boating with access to the ocean.  Relax on the...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$9,500 - $9,500
June 2026
SuMoTuWeThFrSa
 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 2026
SuMoTuWeThFrSaWeek
 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
$9,500
26
27
28
29
30
31
 $9,500
August 2026
SuMoTuWeThFrSaWeek
 1
$9,500
2
3
4
5
6
7
8
$9,500
9
10
11
12
13
14
15
$9,500
16
17
18
19
20
21
22
$9,500
23
24
25
26
27
28
29
$9,500
30
31
 $9,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,500
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: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ARNOS

(0)Inquire/Share
Property Details
Wonderful Family Friendly Home in West Chop Area of Vineyard Haven
Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
6
Baths: 
3
Price Range:
$4,900 - $9,450
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$7,000
28
29
30
 $8,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,400
5
6
7
8
9
10
11
$8,400
12
13
14
15
16
17
18
$8,400
19
20
21
22
23
24
25
$8,400
26
27
28
29
30
31
 $8,550
August 2026
SuMoTuWeThFrSaWeek
 1
$8,550
2
3
4
5
6
7
8
$9,450
9
10
11
12
13
14
15
$9,450
16
17
18
19
20
21
22
$9,450
23
24
25
26
27
28
29
$9,450
30
31
 $7,650
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,650
6
7
8
9
10
11
12
$6,300
13
14
15
16
17
18
19
$6,300
20
21
22
23
24
25
26
$6,300
27
28
29
30
 $6,300
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
Add Favorite
 
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FREE2

(0)Inquire/Share
Property Details
Lovely Historic William St Home, Located just one block from Main St. 4 bedrooms, 4 baths

Beautifully renovated Greek Revival home (the Berkshire House) on historic William Street in Vineyard Haven.

This finely crafted home offers vacationing guests spacious living on three levels. The main level...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,900 - $9,200
June 2026
SuMoTuWeThFrSaWeek
 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
 $9,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,200
5
6
7
8
9
10
11
$9,200
12
13
14
15
16
17
18
$9,200
19
20
21
22
23
24
25
$9,200
26
27
28
29
30
31
 $9,200
August 2026
SuMoTuWeThFrSaWeek
 1
$9,200
2
3
4
5
6
7
8
$9,200
9
10
11
12
13
14
15
$9,200
16
17
18
19
20
21
22
$9,200
23
24
25
26
27
28
29
$9,200
30
31
 $6,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,900
6
7
8
9
10
11
12
$6,900
13
14
15
16
17
18
19
$6,900
20
21
22
23
24
25
26
$5,900
27
28
29
30
 $5,900
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

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