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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 - $9,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
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
$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
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17
$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
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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
14
15
16
17
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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NORMD

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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 - $8,950
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
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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
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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: 
$385
Tax: State & Local: 
11.7

 

 

 

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NAKAJ

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Property Details
Waterfront & View on Edgartown Great Pond, Association Private Beach and Tennis, Central A/C

Waterfront Retreat on Edgartown Great Pond with Private Beach Access & Tennis

MVVR EXCLUSIVE:
Set in a peaceful waterfront location within the desirable Boldwater area, this beautiful contemporary 4-bedroom,...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,200 - $8,900
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,200
6
7
8
9
10
11
12
$3,600
13
14
15
16
17
18
19
$3,600
20
21
22
23
24
25
26
$4,200
27
28
29
30
 $5,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,800
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
$8,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,900
8
9
10
11
12
13
14
$8,900
15
16
17
18
19
20
21
$8,900
22
23
24
25
26
27
28
$8,900
29
30
31
 $3,700
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,700
5
6
7
8
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10
11
$3,250
12
13
14
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16
17
18
$3,250
19
20
21
22
23
24
25
$3,250
26
27
28
29
30
 $3,250
Clean Fee: 
$625 per week
Tax: State & Local: 
11.7

 

 

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KINOL

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Property Details
Elegant Retreat Long Point Beach Area, West Tisbury, Expansive Landscaped Yard, Wrap Around Porch and Deck

Long Point Beach Area beautifully appointed home set on 1.4 acres with manicured lawns, perennial beds, and flowering trees.  Guests are sure to enjoy the expansive wrap-around porch and shaded...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $8,800
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,300
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
27
28
29
30
 
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
$6,300
11
12
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14
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16
17
$6,300
18
19
20
21
22
23
24
$6,300
25
26
27
28
29
30
31
$7,300
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,200
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
$8,800
29
30
31
 $7,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,100
5
6
7
8
9
10
11
$5,000
12
13
14
15
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17
18
$5,000
19
20
21
22
23
24
25
$3,800
26
27
28
29
30
 $3,800
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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ARCAE

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Property Details
Meticulously Maintained Classic Summer Home! Ideally located in the Heart of Katama, Beach in one Direction and Edgartown Village Center in the opposite direction

Location Location in the heart of Katama equidistant between Edgartown Village and South Beach. This beautiful home is tucked on beautifully landscaped acreage. The reverse contemporary design boasts private upper...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
5
Baths: 
2
Price Range:
$4,400 - $8,800
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,700
13
14
15
16
17
18
19
$8,200
20
21
22
23
24
25
26
$8,800
27
28
29
30
 $8,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,800
4
5
6
7
8
9
10
$8,800
11
12
13
14
15
16
17
$8,800
18
19
20
21
22
23
24
$8,800
25
26
27
28
29
30
31
$8,800
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
$8,800
22
23
24
25
26
27
28
$8,800
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
7
8
9
10
11
$5,500
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
 $4,700
Clean Fee: 
$675 per week
Tax: State & Local: 
11.7

Two-week minimum stay required during July and August!  

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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:
$8,300 - $8,800
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
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July 2027
SuMoTuWeThFrSaWeek
 1
2
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4
5
6
7
8
9
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12
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17
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19
20
21
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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
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25
26
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28
29
30
31
 
September 2027
SuMoTuWeThFrSa
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2
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27
28
29
30
 
Clean Fee: 
$575 per week
Tax: State & Local: 
11.7

 

 

 

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PRIAN

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Property Details
Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$8,300 - $8,750
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
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25
26
27
28
29
30
 $8,300
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,300
4
5
6
7
8
9
10
$8,500
11
12
13
14
15
16
17
$8,500
18
19
20
21
22
23
24
$8,750
25
26
27
28
29
30
31
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,900
8
9
10
11
12
13
14
$9,900
15
16
17
18
19
20
21
22
23
24
25
26
27
28
$8,750
29
30
31
 
September 2027
SuMoTuWeThFrSa
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2
3
4
5
6
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8
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25
26
27
28
29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
14.45
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MONVH

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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:
$5,500 - $8,650
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
$6,900
27
28
29
30
 $7,150
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,150
4
5
6
7
8
9
10
$7,150
11
12
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$7,150
18
19
20
21
22
23
24
$7,150
25
26
27
28
29
30
31
$8,650
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,650
8
9
10
11
12
13
14
$8,650
15
16
17
18
19
20
21
$8,650
22
23
24
25
26
27
28
$6,900
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
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17
18
$5,500
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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WHARG

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Property Details
Lovely Home in a quiet Neighborhood. Walk to Town Center and Inkwell Beach, Large Private Deck, Room AC

Spacious sun-filled contemporary home located on a quiet private street, a 10-minute walk to town center, Inkwell Beach, and the harborfront.

The first level features a spacious kitchen with stainless steel...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$7,200 - $8,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,200
6
7
8
9
10
11
12
$7,200
13
14
15
16
17
18
19
$7,200
20
21
22
23
24
25
26
$7,200
27
28
29
30
 $7,200
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,200
4
5
6
7
8
9
10
$7,500
11
12
13
14
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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
$8,500
8
9
10
11
12
13
14
$8,500
15
16
17
18
19
20
21
$8,500
22
23
24
25
26
27
28
$8,500
29
30
31
 $8,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
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: 
$375 per week
Tax: State & Local: 
14.45
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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
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$8,500
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$8,500
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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
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$8,500
5
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25
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27
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29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
Add Favorite
 
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TESTL

Inquire
Property Details
Beautiful Long View Country House, Walk to Lambert's Cove Beach, Central A/C

Extended families will enjoy this lovely 5 bedroom, 3 bath home featuring expanded living space with a first-floor living room and second-floor family/tv room.  Spacious modern kitchen with prep island...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$8,500 - $8,500
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSaWeek
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$8,500
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$8,500
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$8,500
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$8,500
29
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31
 
September 2027
SuMoTuWeThFrSa
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29
30
 
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MONEE

Inquire
Property Details
Outstanding Edgartown Vacation Home, Spacious Coastal Decor Interior, Large Deck, Screened Porch, Just 1.5 miles to the Village Center

Chic Contemporary Farmhouse, just a short distance to Edgartown Village Center, features a quiet and private setting with all-new beach-inspired decor throughout.

The home has an open first-floor layout with the kitchen,...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$3,000 - $8,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
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$5,000
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$5,000
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26
$6,000
27
28
29
30
 $7,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,800
4
5
6
7
8
9
10
$7,800
11
12
13
14
15
16
17
$7,800
18
19
20
21
22
23
24
$7,800
25
26
27
28
29
30
31
$7,800
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,500
8
9
10
11
12
13
14
$8,500
15
16
17
18
19
20
21
$8,500
22
23
24
25
26
27
28
$8,000
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
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
 $5,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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HOD28

Inquire
Property Details
Beautiful Oak Bluffs home just blocks from the Center of Town, Ocean Park and Inkwell Beach.

Note: the kitchen is being completely remodeled for summer 2024 and will have all new high-end appliances, Subzero, Thermador, and new cabinets, and counters. 

Summer Joy!  Set in the heart of...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$5,750 - $8,250
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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
$8,000
27
28
29
30
 $8,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,250
4
5
6
7
8
9
10
$8,400
11
12
13
14
15
16
17
$8,500
18
19
20
21
22
23
24
$8,500
25
26
27
28
29
30
31
$8,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,150
8
9
10
11
12
13
14
$9,150
15
16
17
18
19
20
21
$9,150
22
23
24
25
26
27
28
$9,150
29
30
31
 $6,900
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,900
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
$6,900
26
27
28
29
30
 $6,900
Clean Fee: 
$700 per week
Tax: State & Local: 
14.45

8-minute walk from the ferry dock in Oak Bluffs and 5 minute walk to the Ink Well Beach, and Oak Bluffs Center from the house. 

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BOWDL

Inquire
Property Details
Lovely Custom Contemporary Home, Tucked in the Community of Bayes Hill, 4 Bedrooms, 4 Bath, Landscaped, Deck, Patio Dining Area

Designed with a sophisticated contemporary aesthetic, this chic vacation retreat showcases an open floor plan, expansive windows, and beautifully curated interiors. Offering four bedrooms and 3.5 baths, the home is...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $8,050
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
 $7,750
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,750
4
5
6
7
8
9
10
$7,750
11
12
13
14
15
16
17
$7,750
18
19
20
21
22
23
24
$7,750
25
26
27
28
29
30
31
$8,050
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,050
8
9
10
11
12
13
14
$8,050
15
16
17
18
19
20
21
$8,050
22
23
24
25
26
27
28
$8,050
29
30
31
 $8,050
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,050
5
6
7
8
9
10
11
$7,500
12
13
14
15
16
17
18
$7,500
19
20
21
22
23
24
25
$7,500
26
27
28
29
30
 $7,500
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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MCGRD

Inquire
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
15
16
17
18
19
$5,000
20
21
22
23
24
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
16
17
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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