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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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:
$4,900 - $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

Owner will rent off weekend dates, for arrival and departures. Inquire for details. 

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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:
$9,000 - $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
$9,000
26
27
28
29
30
31
 $9,000
August 2026
SuMoTuWeThFrSaWeek
 1
$9,000
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
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Wondeful Family Friendly Home in West Chop Area of Vineyard Haven
Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
6
Baths: 
3
Price Range:
$3,850 - $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
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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:
$5,400 - $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

Owner reduced rates for available weeks in June, July, August, September  - see calendar for adjusted rates

 

 

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Lovely Newly Renovated Waterfront Home on the Lagoon!

Tucked on Hines Point, a lovely neighborhood of lagoon front homes, this sweet 4 bedroom, 2 bath home has been completely updated and is only a 10-minute walk to Vineyard...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,800 - $8,950
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,100
7
8
9
10
11
12
13
$4,300
14
15
16
17
18
19
20
$4,600
21
22
23
24
25
26
27
$6,100
28
29
30
 $7,550
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,550
5
6
7
8
9
10
11
$7,550
12
13
14
15
16
17
18
$7,950
19
20
21
22
23
24
25
$7,950
26
27
28
29
30
31
 $8,950
August 2026
SuMoTuWeThFrSaWeek
 1
$8,950
2
3
4
5
6
7
8
$8,950
9
10
11
12
13
14
15
$8,950
16
17
18
19
20
21
22
$8,650
23
24
25
26
27
28
29
$6,650
30
31
 $5,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,200
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
 $4,500
Clean Fee: 
$385
Tax: State & Local: 
11.7

 

 

 

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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:
$5,000 - $8,650
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,500
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
$6,900
28
29
30
 $7,150
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,150
5
6
7
8
9
10
11
$5,600
12
13
14
15
16
17
18
$6,100
19
20
21
22
23
24
25
$6,100
26
27
28
29
30
31
 $8,650
August 2026
SuMoTuWeThFrSaWeek
 1
$8,650
2
3
4
5
6
7
8
$8,650
9
10
11
12
13
14
15
$8,650
16
17
18
19
20
21
22
$8,650
23
24
25
26
27
28
29
$6,900
30
31
 $5,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
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
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner reduced rates in July by $1500 per week - see calendar for adjusted rates

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Waterfront on the Shores of a Picturesque Tidal Inlet Lake Tashmoo, Shared Tennis Courts, Spectacular Views & Sunsets,

This lovely three-bedroom home is located on the shores of beautiful Lake Tashmoo (a tidal saltwater lake connecting to Vineyard Sound).  The modern open floor plan includes. kitchen, living, and...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$8,500 - $8,500
June 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
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23
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25
26
27
28
29
30
 
July 2026
SuMoTuWeThFrSa
 1
2
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5
6
7
8
9
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11
12
13
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23
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25
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
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
 $8,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,500
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: 
$375 per week
Tax: State & Local: 
11.7
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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
SuMoTuWeThFrSaWeek
 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
SuMoTuWeThFrSaWeek
 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
SuMoTuWeThFrSaWeek
 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
SuMoTuWeThFrSaWeek
 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.

 

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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 .

The essence of summer vacation living shines in this beautiful custom post-and-beam home, nestled in the private Makonikey community of Vineyard Haven, Martha’s Vineyard. Just a short quarter-mile walk to...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$7,300 - $8,500
June 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
26
27
28
29
30
 $7,300
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,300
5
6
7
8
9
10
11
$7,300
12
13
14
15
16
17
18
$7,300
19
20
21
22
23
24
25
$7,300
26
27
28
29
30
31
 $7,300
August 2026
SuMoTuWeThFrSaWeek
 1
$7,300
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
 
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: 
$575 per week
Tax: State & Local: 
11.7

Rates reduced for available weeks in July - see calendar for adjusted rates

 

 

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Outer Harbor Waterfront, Private Sandy Beach, Lush Gardens and Large Yard, Magnificent Water Views

Relax and enjoy the picturesque views of the outer harbor, with its plethora of boats going by each day, from the screened Gazebo, porch, and patio areas. The wide, sandy private beach...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$4,500 - $8,400
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,700
7
8
9
10
11
12
13
$5,100
14
15
16
17
18
19
20
$5,100
21
22
23
24
25
26
27
$8,100
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
$9,250
26
27
28
29
30
31
 $9,300
August 2026
SuMoTuWeThFrSaWeek
 1
$9,300
2
3
4
5
6
7
8
$9,350
9
10
11
12
13
14
15
$9,400
16
17
18
19
20
21
22
$9,400
23
24
25
26
27
28
29
$8,400
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
 $4,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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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

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,250 - $7,990
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,990
7
8
9
10
11
12
13
$7,990
14
15
16
17
18
19
20
$7,990
21
22
23
24
25
26
27
$7,990
28
29
30
 $9,650
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,650
5
6
7
8
9
10
11
$9,650
12
13
14
15
16
17
18
$9,650
19
20
21
22
23
24
25
$9,650
26
27
28
29
30
31
 $9,650
August 2026
SuMoTuWeThFrSaWeek
 1
$9,650
2
3
4
5
6
7
8
$9,650
9
10
11
12
13
14
15
$9,650
16
17
18
19
20
21
22
$9,650
23
24
25
26
27
28
29
$9,650
30
31
 $7,990
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,990
6
7
8
9
10
11
12
$7,990
13
14
15
16
17
18
19
$7,990
20
21
22
23
24
25
26
$6,990
27
28
29
30
 $6,990
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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Gorgeous Water views, set in private Mink Meadows Golf Course Community , Private Association Beach, Walk or drive to the Golf Course Club House

Beautiful home in Mink Meadows area of West Chop.  Guests will enjoy the gorgeous water views across Mink Meadows Pond to the North Shore. Swans, geese, and ducks reside in the...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $7,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$5,200
14
15
16
17
18
19
20
$5,200
21
22
23
24
25
26
27
$5,200
28
29
30
 $7,750
July 2026
SuMoTuWeThFrSaWeek
 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
 $7,900
August 2026
SuMoTuWeThFrSaWeek
 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
 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

 Transferrable ferry tickets available for 8/31 to 9/13,  and 9/13 to 9/27.   

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Lovely Vineyard Haven Home, Heated Pool, AC, Close Proximity to Towns and Beaches , Perfect Home for Extended Families.

Spacious Vacation Home with heated pool!  This lovely home is perfect for extended families featuring 5 bedrooms, 3 baths, multiple living spaces, and 5 TVs. The pool and deck are perfect...Read more

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

POOL HEATED TO 80 DEGREES JULY AND AUGUST WEEKS INCLUDED IN RENTAL RATE.

POOL HEATED TO 80 DEGREES JUNE AND SEPTEMBER WEEKS ADDITIONAL $275 PER WEEK

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5 minute walk to town center.

Enjoy a view of Vineyard Haven harbor from this 1898 Captain's home. Walk to town, tennis, dining, library, etc... The Captain Henry Stevenson house has been renovated to include a...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$5,900 - $7,400
June 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
26
27
28
29
30
 $7,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,400
5
6
7
8
9
10
11
$7,400
12
13
14
15
16
17
18
$7,400
19
20
21
22
23
24
25
$7,400
26
27
28
29
30
31
 $7,400
August 2026
SuMoTuWeThFrSaWeek
 1
$7,400
2
3
4
5
6
7
8
$7,400
9
10
11
12
13
14
15
$7,400
16
17
18
19
20
21
22
$6,900
23
24
25
26
27
28
29
$6,900
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: 
$350 per week
Tax: State & Local: 
11.7
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Perfect Beach Front Cottage. Expansive Water Views, Gorgeous Sunsets, Pristine Modern Interior

Privately nestled atop a dune with breathtaking views and just steps from a private swimming beach. This immaculate 2 bedroom, 1 bath beachfront cottage offers a tastefully furnished interior with sun-filled rooms...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$4,040 - $7,090
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,530
7
8
9
10
11
12
13
$5,530
14
15
16
17
18
19
20
$5,530
21
22
23
24
25
26
27
$5,530
28
29
30
 $7,090
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,090
5
6
7
8
9
10
11
$7,090
12
13
14
15
16
17
18
$7,090
19
20
21
22
23
24
25
$7,090
26
27
28
29
30
31
 $7,090
August 2026
SuMoTuWeThFrSaWeek
 1
$7,090
2
3
4
5
6
7
8
$7,090
9
10
11
12
13
14
15
$7,090
16
17
18
19
20
21
22
$7,090
23
24
25
26
27
28
29
$6,560
30
31
 $6,040
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,040
6
7
8
9
10
11
12
$5,510
13
14
15
16
17
18
19
$4,990
20
21
22
23
24
25
26
$4,990
27
28
29
30
 $4,460
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

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