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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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
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$6,000
6
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$6,000
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$6,000
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$6,000
27
28
29
30
 $7,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,500
4
5
6
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10
$7,150
11
12
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$8,000
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$8,000
25
26
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30
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$9,000
August 2027
SuMoTuWeThFrSaWeek
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2
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$9,000
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$9,000
15
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$9,000
22
23
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25
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28
$8,000
29
30
31
 $6,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,500
5
6
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$6,500
12
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$6,000
19
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$6,000
26
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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MOORD~

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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
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July 2027
SuMoTuWeThFrSaWeek
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$8,300
25
26
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30
31
$8,300
August 2027
SuMoTuWeThFrSaWeek
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2
3
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7
$8,800
8
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$8,800
15
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30
31
 
September 2027
SuMoTuWeThFrSa
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29
30
 
Clean Fee: 
$575 per week
Tax: State & Local: 
11.7

 

 

 

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KERR3

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Property Details
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 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSaWeek
1
2
3
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5
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7
$8,500
8
9
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14
$8,500
15
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$8,500
22
23
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28
$8,500
29
30
31
 $8,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
6
7
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12
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15
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19
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25
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27
28
29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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ARNOS~

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

Note: Exterrior Security Cameras Present On PropertyRead more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
6
Baths: 
3
Price Range:
$4,200 - $8,400
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
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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
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$6,300
12
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$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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CLE20

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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 - $8,100
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$5,500
13
14
15
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$5,500
20
21
22
23
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25
26
$8,100
27
28
29
30
 $8,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,500
4
5
6
7
8
9
10
$9,000
11
12
13
14
15
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$9,000
18
19
20
21
22
23
24
$9,500
25
26
27
28
29
30
31
$10,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,500
8
9
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11
12
13
14
$10,500
15
16
17
18
19
20
21
$10,500
22
23
24
25
26
27
28
$10,000
29
30
31
 $6,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,000
5
6
7
8
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10
11
$5,500
12
13
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18
$5,500
19
20
21
22
23
24
25
$5,500
26
27
28
29
30
 $4,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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MCGRD~

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Property Details
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 - $8,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$5,000
13
14
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$5,000
20
21
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25
26
$5,000
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
$8,000
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
$7,000
29
30
31
 $5,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
7
8
9
10
11
$5,000
12
13
14
15
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18
$5,000
19
20
21
22
23
24
25
$4,000
26
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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CHAMV~

Inquire
Property Details
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 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,990
6
7
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9
10
11
12
$7,990
13
14
15
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17
18
19
$7,990
20
21
22
23
24
25
26
$7,990
27
28
29
30
 $10,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$10,500
4
5
6
7
8
9
10
$10,500
11
12
13
14
15
16
17
$10,500
18
19
20
21
22
23
24
$10,500
25
26
27
28
29
30
31
$10,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,500
8
9
10
11
12
13
14
$10,500
15
16
17
18
19
20
21
$10,500
22
23
24
25
26
27
28
$10,500
29
30
31
 $7,990
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,990
5
6
7
8
9
10
11
$7,990
12
13
14
15
16
17
18
$7,990
19
20
21
22
23
24
25
$7,990
26
27
28
29
30
 $6,990
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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PE585~

Inquire
Property Details
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 - $7,450
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,810
6
7
8
9
10
11
12
$5,810
13
14
15
16
17
18
19
$5,810
20
21
22
23
24
25
26
$5,810
27
28
29
30
 $7,450
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,450
4
5
6
7
8
9
10
$7,450
11
12
13
14
15
16
17
$7,450
18
19
20
21
22
23
24
$7,450
25
26
27
28
29
30
31
$7,450
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,450
8
9
10
11
12
13
14
$7,450
15
16
17
18
19
20
21
$7,450
22
23
24
25
26
27
28
$6,890
29
30
31
 $6,350
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,350
5
6
7
8
9
10
11
$5,790
12
13
14
15
16
17
18
$5,240
19
20
21
22
23
24
25
$5,240
26
27
28
29
30
 $4,690
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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NORMD~

Inquire
Property Details
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 - $7,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,100
6
7
8
9
10
11
12
$4,300
13
14
15
16
17
18
19
$4,600
20
21
22
23
24
25
26
$6,100
27
28
29
30
 $7,540
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,540
4
5
6
7
8
9
10
$7,540
11
12
13
14
15
16
17
$7,950
18
19
20
21
22
23
24
$7,950
25
26
27
28
29
30
31
$8,950
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,950
8
9
10
11
12
13
14
$8,950
15
16
17
18
19
20
21
$8,950
22
23
24
25
26
27
28
$7,200
29
30
31
 $5,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,200
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
 $4,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

 

 

 

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DELOA~

Inquire
Property Details
Ramble House, Lovely, Spacious 3 Bedroom, 3 bath Vacation Home. Tucked on a Tranquil Street in Vineyard Haven, Multiple Living Spaces Indoor & Outdoor, Impeccably Maintained.

A tranquil oasis just outside Vineyard Haven and only one mile from the village center, this spacious and inviting three-bedroom, three-bath home is tucked away at the end of a...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$3,500 - $6,900
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $5,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,900
4
5
6
7
8
9
10
$5,900
11
12
13
14
15
16
17
$5,900
18
19
20
21
22
23
24
$5,900
25
26
27
28
29
30
31
$6,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,900
8
9
10
11
12
13
14
$6,900
15
16
17
18
19
20
21
$6,900
22
23
24
25
26
27
28
$6,900
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$4,000
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: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
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NORTO

Inquire
Property Details
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:
$5,500 - $6,750
June 2027
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
$5,500
27
28
29
30
 $6,750
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,750
4
5
6
7
8
9
10
$6,750
11
12
13
14
15
16
17
$6,750
18
19
20
21
22
23
24
$6,750
25
26
27
28
29
30
31
$6,750
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,750
8
9
10
11
12
13
14
$6,750
15
16
17
18
19
20
21
$6,750
22
23
24
25
26
27
28
$6,750
29
30
31
 $5,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$5,500
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: 
$550 per week
Tax: State & Local: 
11.7
Add Favorite
 
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STA24~

Inquire
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:
$5,900 - $6,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,900
6
7
8
9
10
11
12
$5,900
13
14
15
16
17
18
19
$5,900
20
21
22
23
24
25
26
$5,900
27
28
29
30
 $6,200
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,200
4
5
6
7
8
9
10
$6,200
11
12
13
14
15
16
17
$6,200
18
19
20
21
22
23
24
$6,200
25
26
27
28
29
30
31
$6,200
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,200
8
9
10
11
12
13
14
$6,200
15
16
17
18
19
20
21
$6,200
22
23
24
25
26
27
28
$6,200
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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FRISD~

Inquire
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:
$3,500 - $6,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$3,800
13
14
15
16
17
18
19
$3,900
20
21
22
23
24
25
26
$4,600
27
28
29
30
 $5,100
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,100
4
5
6
7
8
9
10
$6,000
11
12
13
14
15
16
17
$6,000
18
19
20
21
22
23
24
25
26
27
28
29
30
31
August 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
$5,000
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$3,800
12
13
14
15
16
17
18
$3,800
19
20
21
22
23
24
25
$3,800
26
27
28
29
30
 $3,800
Clean Fee: 
$390 per week
Tax: State & Local: 
11.7
Add Favorite
 
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GRILJ~

Inquire
Property Details
Lovely Custom Post & Beam Home, Tucked on Gorgeous Private Acreage, 1.5 Miles from the Center of Vineyard Haven.

Martha’s Vineyard Vacation Rental – Private Vineyard Haven Retreat

This lovely and spacious Martha’s Vineyard vacation rental offers all the comforts of home in a serene, private setting. Set on...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,700 - $6,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
27
28
29
30
 $4,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,800
4
5
6
7
8
9
10
$4,800
11
12
13
14
15
16
17
$4,800
18
19
20
21
22
23
24
$4,800
25
26
27
28
29
30
31
$5,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000
8
9
10
11
12
13
14
$6,000
15
16
17
18
19
20
21
$6,000
22
23
24
25
26
27
28
$5,200
29
30
31
 $3,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,500
5
6
7
8
9
10
11
$3,000
12
13
14
15
16
17
18
$3,000
19
20
21
22
23
24
25
$3,000
26
27
28
29
30
 $3,000
Clean Fee: 
$575
Tax: State & Local: 
11.7
Add Favorite
 
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STA50

Inquire
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:
$4,900 - $5,900
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
 $4,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,900
4
5
6
7
8
9
10
$4,900
11
12
13
14
15
16
17
$4,900
18
19
20
21
22
23
24
$4,900
25
26
27
28
29
30
31
$5,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,900
8
9
10
11
12
13
14
$5,900
15
16
17
18
19
20
21
$5,900
22
23
24
25
26
27
28
$4,900
29
30
31
 $4,900
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,900
5
6
7
8
9
10
11
$4,900
12
13
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

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