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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In-Town, Water View, Waterfront

Enjoy expansive harbor views and passing tall-masted schooners from the breezy wrap-around porch of this delightful five-bedroom classic Vineyard home over the harbor. Stroll to the village center, tennis, fine...Read more

Location: 
Vineyard Haven
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$10 - $6,000
June 2025
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
29
30
 $6,000
July 2025
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$6,000
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 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,000
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$6,000
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$6,000
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$6,000
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30
$6,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
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2
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$4,000
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$4,000
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$4,000
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27
$4,000
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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STA24

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Property Details
Lovely All Newly Furnished Home, Walk to Vineyard Haven Village Center

Perfectly located for those who love to walk! Vineyard Haven Yacht Club, Main St with its lovely shops, and the Vineyard Haven library are all within a 10-minute walk from...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $6,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$4,400
15
16
17
18
19
20
21
$4,400
22
23
24
25
26
27
28
$4,400
29
30
 $5,400
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,400
6
7
8
9
10
11
12
$5,600
13
14
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18
19
$5,600
20
21
22
23
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26
$5,600
27
28
29
30
31
 $5,700
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,700
3
4
5
6
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8
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$5,900
10
11
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$6,000
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18
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23
$6,000
24
25
26
27
28
29
30
$5,900
31
 $5,400
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$5,400
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$5,400
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15
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17
18
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21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

 

 

 

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STA50

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Property Details
Adorable 2 Bedroom, 1 Bath Cottage, Large Private Back Yard, Deck, Walk to Vineyard Haven Center

Adorable light-filled cottage, with modern furnishings, this lovely 2 bedroom home is situated on a large lot on a quiet street just on the outskirts of Vineyard Haven Center.  The home has a...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$10 - $5,900
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
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10
11
12
13
14
15
16
17
18
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21
22
23
24
25
26
27
28
29
30
 $4,900
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,900
6
7
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$4,900
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19
$4,900
20
21
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$4,900
27
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30
31
 $5,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,900
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$5,900
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$5,900
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$5,900
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26
27
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29
30
$4,900
31
 $4,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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5
6
$4,900
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8
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$4,900
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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JOHNE

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Property Details
Lovely Tashmoo Cove Condo, Heated Association Pool, Association Tennis Courts, Deck with Patio Dining. 2 Miles to Town Center

Nestled in the lovely private community of homes and condos,  this charming 2 bedroom, 2.5 bath unit is just a five-minute walk to the association pool and tennis courts,  Located  two miles from...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$10 - $5,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,250
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9
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14
$4,250
15
16
17
18
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20
21
$4,250
22
23
24
25
26
27
28
$4,250
29
30
 $5,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
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10
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12
$5,500
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14
15
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$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
31
 $5,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,500
3
4
5
6
7
8
9
$5,800
10
11
12
13
14
15
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$5,800
17
18
19
20
21
22
23
$5,800
24
25
26
27
28
29
30
$5,800
31
 $4,250
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,250
7
8
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10
11
12
13
$4,250
14
15
16
17
18
19
20
$4,250
21
22
23
24
25
26
27
$4,250
28
29
30
 $4,250
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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ARNOP

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Property Details
West Chop Area, Central Air

Country Cottage Retreat. This completely renovated gem is located just at the head of the West Chop area in Vineyard Haven. The interior layout features four bedrooms, 2.5 baths, a...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $5,600
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
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14
$3,500
15
16
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18
19
20
21
$3,500
22
23
24
25
26
27
28
$4,000
29
30
 $5,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,600
6
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$5,600
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$5,600
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$5,600
27
28
29
30
31
 $5,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,600
3
4
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$5,600
10
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$5,600
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18
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21
22
23
$5,600
24
25
26
27
28
29
30
$5,600
31
 $4,250
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,250
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$3,500
28
29
30
 $3,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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BORAR

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Property Details
Lovely, Recently Update West Chop Area Home, Spacious Deck, Opening Living Spaces, 15 Minute Walk to Town

This lovely, spacious, airy home was recently renovated, an open-concept home filled with natural light and located on a private road. Your next “home away from home” is perfectly located minutes from all...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $5,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$3,500
22
23
24
25
26
27
28
$3,800
29
30
 $4,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,800
6
7
8
9
10
11
12
$4,800
13
14
15
16
17
18
19
$4,800
20
21
22
23
24
25
26
$4,800
27
28
29
30
31
 $5,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,500
3
4
5
6
7
8
9
$5,500
10
11
12
13
14
15
16
$5,800
17
18
19
20
21
22
23
$4,800
24
25
26
27
28
29
30
$4,400
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$3,500
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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HARTM

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Property Details
Charming & Cozy 2 Bedroom, 2 Bath Home, West Chop area of Vineyard Haven, Located on a Quiet Street & Close to Town & Beach

Ideally located in the West Chop woods area of Vineyard Haven, just 1 mile to town center and the business district, and a 10 to 15-minute drive to various public...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$10 - $5,150
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,850
8
9
10
11
12
13
14
$3,850
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $4,650
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,650
6
7
8
9
10
11
12
$4,850
13
14
15
16
17
18
19
$4,850
20
21
22
23
24
25
26
$4,850
27
28
29
30
31
 $4,850
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,850
3
4
5
6
7
8
9
$5,150
10
11
12
13
14
15
16
$5,150
17
18
19
20
21
22
23
$5,150
24
25
26
27
28
29
30
$5,150
31
 $3,300
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,300
7
8
9
10
11
12
13
$3,200
14
15
16
17
18
19
20
$3,200
21
22
23
24
25
26
27
$3,200
28
29
30
 $2,700
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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FRISD

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Property Details
Adorable, Chic In -Town Home, Coastal Décor, Central AC, Large Bluestone Patio plus a Farmers Porch for Summer Outdoor Enjoyment

Charming is the description for this newly furnished in-town summer cottage-style home. The house boasts multiple outdoor living spaces, including a large, secluded bluestone patio with an outdoor living room, a patio dining and grill...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $5,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$3,500
22
23
24
25
26
27
28
$4,000
29
30
 $4,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,800
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
31
 $5,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,000
3
4
5
6
7
8
9
$5,000
10
11
12
13
14
15
16
$5,000
17
18
19
20
21
22
23
$5,000
24
25
26
27
28
29
30
$4,800
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$3,500
28
29
30
 $3,500
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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SAVAJ

(0)Inquire/Share
Property Details
Tashmoo Cove Townhouse, Association Pool, Association Tennis Courts.

MVVR Exclusive: Beautifully appointed with a mix of Asian and Tibetan antique furniture, furnishings from Napa Valley, Sundance, and Pottery Barn, and original artwork, this highly desirable townhouse provides a luxurious...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$10 - $4,600
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,420
8
9
10
11
12
13
14
$3,220
15
16
17
18
19
20
21
$3,220
22
23
24
25
26
27
28
$3,500
29
30
 $4,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,200
6
7
8
9
10
11
12
$4,200
13
14
15
16
17
18
19
$4,200
20
21
22
23
24
25
26
$4,200
27
28
29
30
31
 $4,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,600
3
4
5
6
7
8
9
$4,700
10
11
12
13
14
15
16
$4,700
17
18
19
20
21
22
23
$4,700
24
25
26
27
28
29
30
$3,900
31
 $3,100
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,100
7
8
9
10
11
12
13
$3,100
14
15
16
17
18
19
20
$2,700
21
22
23
24
25
26
27
$2,200
28
29
30
 $2,200
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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HALLL

(0)Inquire/Share
Property Details
Makonikey, Water View, Walk to Private Association Beach, Large Yard Area.

Located in Makonikey,  a private enclave of homes on the North Shore.

Beautifully maintained four-bedroom vacation home with water views. Just a short walk or drive to private Makonikey association beach,  This...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $4,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,800
8
9
10
11
12
13
14
$3,800
15
16
17
18
19
20
21
$3,800
22
23
24
25
26
27
28
$4,400
29
30
 $4,500
July 2025
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
31
 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,500
3
4
5
6
7
8
9
$4,500
10
11
12
13
14
15
16
$4,500
17
18
19
20
21
22
23
$4,500
24
25
26
27
28
29
30
$4,500
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$3,800
14
15
16
17
18
19
20
$3,800
21
22
23
24
25
26
27
$3,800
28
29
30
 $3,500
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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THEOK

(0)Inquire/Share
Property Details
Lovely Cape Home, Newly Updated, Private Back Deck with Outdoor Dining & Grill, 3 Bedrooms w/AC and TV, 1.5 baths

Nestled on a serene lane in the outskirts of Vineyard Haven, this newly updated Cape Style residence exudes chic charm. Step inside to discover an inviting open layout on the...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$10 - $4,400
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,500
29
30
 $3,700
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,700
6
7
8
9
10
11
12
$3,700
13
14
15
16
17
18
19
$3,700
20
21
22
23
24
25
26
$3,700
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
12
13
14
15
16
$4,400
17
18
19
20
21
22
23
$4,400
24
25
26
27
28
29
30
$4,000
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$3,000
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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WILLD

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Property Details
The Sweetest In-town Cottage! 2 Minute Walk to Main St

This adorable cottage-style home features 2 bedrooms, and 2 baths and is tucked in on a tiny side street off of Main St. Walk to all that the village center...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$10 - $4,200
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$3,500
22
23
24
25
26
27
28
$3,500
29
30
 $3,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,800
6
7
8
9
10
11
12
$3,800
13
14
15
16
17
18
19
$3,800
20
21
22
23
24
25
26
$3,800
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
12
13
14
15
16
$4,000
17
18
19
20
21
22
23
$4,200
24
25
26
27
28
29
30
$4,200
31
 $3,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$3,000
28
29
30
 $2,250
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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KRAFM

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Property Details
Pristine Bungalow, Peekaboo Water View of Lagoon, Private Path to the Lagoon Waterfront from the Yard, 2 Kayaks Provided

THOREAU'S SPIRIT LIVES - An original 1920's summer bungalow lovingly restored to perfection. Two plus acres of quiet comfort, surrounded by farmland and woods. Walk down the long lawn past...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $3,700
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$1,900
8
9
10
11
12
13
14
$2,300
15
16
17
18
19
20
21
$2,300
22
23
24
25
26
27
28
$2,950
29
30
 $2,950
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,950
6
7
8
9
10
11
12
$2,950
13
14
15
16
17
18
19
$2,950
20
21
22
23
24
25
26
$3,200
27
28
29
30
31
 $3,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,200
3
4
5
6
7
8
9
$3,200
10
11
12
13
14
15
16
$3,200
17
18
19
20
21
22
23
$3,700
24
25
26
27
28
29
30
$2,950
31
 $2,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,000
7
8
9
10
11
12
13
$2,000
14
15
16
17
18
19
20
$2,000
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ROBER

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Property Details
Cozy, newly updated Vineyard Haven Cottage, 2 Bedrooms, 1 Bath, Sleeps 4. Spacious Deck with Dining Area & Grill

Nestled on the outskirts of Vineyard Haven, this charming cottage is ideal for small families or two couples seeking a serene retreat. Just a leisurely 15-minute stroll from Main St,...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$10 - $3,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,700
8
9
10
11
12
13
14
$2,700
15
16
17
18
19
20
21
$2,700
22
23
24
25
26
27
28
$3,000
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 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
31
 $3,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,500
3
4
5
6
7
8
9
$3,500
10
11
12
13
14
15
16
$3,500
17
18
19
20
21
22
23
$3,500
24
25
26
27
28
29
30
$3,500
31
 $3,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
7
8
9
10
11
12
13
$2,500
14
15
16
17
18
19
20
$2,500
21
22
23
24
25
26
27
$2,500
28
29
30
 $2,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MILLR

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Property Details
Tashmoo Cove Condominium, Association Pool, Tennis and Beach, Central Air

Set in Tashmoo Woods, an enclave of private homes and condominium units with association amenities,- pool and tennis courts just a short walk from the unit. This unit has a private deck with...Read more

Location: 
Vineyard Haven
Sleeps: 
5
Bedrooms: 
2
Baths: 
3
Price Range:
$10 - $3,000
June 2025
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
$2,770
29
30
 $2,770
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,770
6
7
8
9
10
11
12
$2,770
13
14
15
16
17
18
19
$2,770
20
21
22
23
24
25
26
$2,770
27
28
29
30
31
 $2,770
August 2025
SuMoTuWeThFrSaWeek
 1
2
$2,770
3
4
5
6
7
8
9
$3,000
10
11
12
13
14
15
16
$3,000
17
18
19
20
21
22
23
$3,000
24
25
26
27
28
29
30
$3,000
31
 $3,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$3,000
28
29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Owner requires 2 week minimum stay August and September weeks

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