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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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
SuMoTuWeThFrSaWeek
 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
SuMoTuWeThFrSaWeek
 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
SuMoTuWeThFrSaWeek
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
SuMoTuWeThFrSaWeek
 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! 

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COS67

Inquire
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:
$6,000 - $24,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
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
 $7,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,500
4
5
6
7
8
9
10
$7,500
11
12
13
14
15
16
17
$7,500
18
19
20
21
22
23
24
$7,500
25
26
27
28
29
30
31
$7,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,000
8
9
10
11
12
13
14
$24,500
15
16
17
18
19
20
21
$24,500
22
23
24
25
26
27
28
$8,500
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
7
8
9
10
11
$6,500
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$6,500
26
27
28
29
30
 $6,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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HODGE~

Inquire
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: 
5
Price Range:
$8,500 - $22,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$14,250
6
7
8
9
10
11
12
$14,250
13
14
15
16
17
18
19
$14,250
20
21
22
23
24
25
26
$14,250
27
28
29
30
 $20,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$20,250
4
5
6
7
8
9
10
$20,250
11
12
13
14
15
16
17
$20,250
18
19
20
21
22
23
24
$22,500
25
26
27
28
29
30
31
$25,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$25,500
8
9
10
11
12
13
14
$25,500
15
16
17
18
19
20
21
$25,500
22
23
24
25
26
27
28
$22,000
29
30
31
 $14,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$14,000
5
6
7
8
9
10
11
$12,000
12
13
14
15
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17
18
$11,000
19
20
21
22
23
24
25
$11,000
26
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 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$16,500
27
28
29
30
 $16,750
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$16,750
4
5
6
7
8
9
10
$16,750
11
12
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14
15
16
17
$16,750
18
19
20
21
22
23
24
$18,500
25
26
27
28
29
30
31
$20,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$20,500
8
9
10
11
12
13
14
$20,500
15
16
17
18
19
20
21
$18,500
22
23
24
25
26
27
28
$16,000
29
30
31
 $10,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,000
5
6
7
8
9
10
11
$10,000
12
13
14
15
16
17
18
$10,000
19
20
21
22
23
24
25
$10,000
26
27
28
29
30
 $10,000
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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THOHP

Inquire
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:
$18,000 - $18,000
June 2027
SuMoTuWeThFrSa
 1
2
3
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5
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26
27
28
29
30
 
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
$18,000
11
12
13
14
15
16
17
$18,000
18
19
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24
25
26
27
28
29
30
31
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$20,000
8
9
10
11
12
13
14
$20,000
15
16
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18
19
20
21
$20,000
22
23
24
25
26
27
28
$18,000
29
30
31
 
September 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
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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~

Inquire
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 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,000
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
 $13,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$13,000
4
5
6
7
8
9
10
$13,000
11
12
13
14
15
16
17
$13,000
18
19
20
21
22
23
24
$13,000
25
26
27
28
29
30
31
$16,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$16,000
8
9
10
11
12
13
14
$16,000
15
16
17
18
19
20
21
$16,000
22
23
24
25
26
27
28
$14,000
29
30
31
 $11,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
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
 $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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CLARA~

Inquire
Property Details
Exclusive Makonikey Area Home, Private Landscaped Yard, Large Deck Area, 4 bedrooms & 4 Baths. Short Drive to Towns and Multiple Beaches

Family and friends are sure to enjoy this pristinely maintained and spacious home situated in a private and quiet location. Beautiful yard and deck area with outdoor seating and a patio dining area that...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$4,000 - $13,000
June 2027
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
26
27
28
29
30
 $5,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,000
4
5
6
7
8
9
10
$5,000
11
12
13
14
15
16
17
$5,500
18
19
20
21
22
23
24
$6,500
25
26
27
28
29
30
31
$7,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,000
8
9
10
11
12
13
14
$13,000
15
16
17
18
19
20
21
$10,000
22
23
24
25
26
27
28
$6,000
29
30
31
 $6,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,000
5
6
7
8
9
10
11
$5,500
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
 $4,000
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Sheets & Towels are not provided. Rental guests need to bring sheets & towels, or they can be rented and delivered per the instructions from the linen rental company. www.marthaslinenrental.com

 

 

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SHAJO~

Inquire
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:
$5,500 - $13,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $9,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,500
4
5
6
7
8
9
10
$9,500
11
12
13
14
15
16
17
$9,500
18
19
20
21
22
23
24
$9,500
25
26
27
28
29
30
31
$13,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,000
8
9
10
11
12
13
14
$13,000
15
16
17
18
19
20
21
$13,000
22
23
24
25
26
27
28
$12,000
29
30
31
 $8,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,000
5
6
7
8
9
10
11
$8,000
12
13
14
15
16
17
18
$5,500
19
20
21
22
23
24
25
$5,500
26
27
28
29
30
 $5,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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BAYLM

Inquire
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:
$12,000 - $12,000
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
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July 2027
SuMoTuWeThFrSa
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31
August 2027
SuMoTuWeThFrSaWeek
1
2
3
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7
$12,000
8
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$12,000
15
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21
$12,000
22
23
24
25
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28
29
30
31
 
September 2027
SuMoTuWeThFrSa
 1
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25
26
27
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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SAGID~

Inquire
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 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,800
6
7
8
9
10
11
12
$5,800
13
14
15
16
17
18
19
20
21
22
23
24
25
26
$6,800
27
28
29
30
 $11,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,000
4
5
6
7
8
9
10
$11,000
11
12
13
14
15
16
17
$11,000
18
19
20
21
22
23
24
$12,000
25
26
27
28
29
30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,000
8
9
10
11
12
13
14
$12,000
15
16
17
18
19
20
21
$12,000
22
23
24
25
26
27
28
$10,000
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
7
8
9
10
11
$6,500
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$6,500
26
27
28
29
30
 $5,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

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kerr413-01-exterior.jpg
 
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KERR4

Inquire
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:
$9,900 - $10,000
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
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8
9
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July 2027
SuMoTuWeThFrSaWeek
 1
2
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4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
$9,900
25
26
27
28
29
30
31
$9,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,900
8
9
10
11
12
13
14
$10,000
15
16
17
18
19
20
21
$9,900
22
23
24
25
26
27
28
$9,900
29
30
31
 $9,900
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,900
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: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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FREE2~

Inquire
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 - $9,250
June 2027
SuMoTuWeThFrSaWeek
 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
 $9,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,250
4
5
6
7
8
9
10
$9,250
11
12
13
14
15
16
17
$9,250
18
19
20
21
22
23
24
$9,250
25
26
27
28
29
30
31
$9,250
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,250
8
9
10
11
12
13
14
$9,250
15
16
17
18
19
20
21
$9,250
22
23
24
25
26
27
28
$9,250
29
30
31
 
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
$6,900
12
13
14
15
16
17
18
$6,900
19
20
21
22
23
24
25
$5,900
26
27
28
29
30
 $5,900
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

 

Add Favorite
 
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MONVH~

Inquire
Property Details
Quintessential Vineyard Haven Home, Beautifully Furnished, Surrounded by Large Mature Landscaped Yard, Porch Seating, Multiple Living Spaces Within

Classic Vineyard home set on a quiet street of similar homes. Modern interior with multiple living spaces include a large family room centered around the media area with a sectional sofa...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$6,000 - $9,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
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
 $7,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,500
4
5
6
7
8
9
10
$7,150
11
12
13
14
15
16
17
$8,000
18
19
20
21
22
23
24
$8,000
25
26
27
28
29
30
31
$9,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,000
8
9
10
11
12
13
14
$9,000
15
16
17
18
19
20
21
$9,000
22
23
24
25
26
27
28
$8,000
29
30
31
 $6,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,500
5
6
7
8
9
10
11
$6,500
12
13
14
15
16
17
18
$6,000
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MOORD~

Inquire
Property Details
Charming Post & Beam Home, Tucked on a Private Lot in the Desirable Makonikey Community of Homes, Walk to Private Association Beach, Multiple Indoor/Outdoor Living Spaces .

Note: New for 2026. 

Two of the baths seen in current photos are being gutted and all newly updated. Walk-in glass showers in both, a soaking tub in one, and all new fixtures, sinks, toilets,...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$8,800 - $8,800
June 2027
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 2027
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
$8,300
25
26
27
28
29
30
31
$8,300
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,800
8
9
10
11
12
13
14
$8,800
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2027
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: 
$575 per week
Tax: State & Local: 
11.7

 

 

 

Add Favorite
 
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ARNOS~

Inquire
Property Details
Wonderful Family Friendly Home in West Chop Area of Vineyard Haven

Note: Exterior Security Cameras Present On PropertyRead more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
6
Baths: 
3
Price Range:
$4,200 - $8,100
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,700
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
$7,000
27
28
29
30
 $8,400
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,400
4
5
6
7
8
9
10
$8,400
11
12
13
14
15
16
17
$8,400
18
19
20
21
22
23
24
$8,400
25
26
27
28
29
30
31
$8,400
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,450
8
9
10
11
12
13
14
$9,450
15
16
17
18
19
20
21
$9,450
22
23
24
25
26
27
28
$9,450
29
30
31
 $8,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,100
5
6
7
8
9
10
11
$6,300
12
13
14
15
16
17
18
$6,300
19
20
21
22
23
24
25
$6,300
26
27
28
29
30
 $6,300
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

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