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Modern, Light filled Home, Located at end of Quiet Street, 1.5 Miles to Oak Bluffs center, Harbor Area and one of many Public Beaches

Perfect Oak Bluffs vacation home.  Located just 1.5 miles to the village center, town beach, and centrally located to the towns of Vineyard Haven, Edgartown, and multiple public beaches.  This...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$2,300 - $3,600
June 2027
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$3,600
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 $3,600
July 2027
SuMoTuWeThFrSaWeek
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$3,600
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$3,600
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$3,600
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$3,600
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$3,600
August 2027
SuMoTuWeThFrSaWeek
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$3,600
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$3,600
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$3,600
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$3,600
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30
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 $3,100
September 2027
SuMoTuWeThFrSaWeek
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2
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$3,100
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$2,800
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$2,800
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$2,800
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29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
14.45
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Cottage with Screened Porch, Close to Menemsha Village Area and just a Short Drive to Lucy Vincent Beacn

Menemsha Crossroads sweet cottage in a private wooded area, perfect for a family of four. Features 2 bedrooms, a primary with bath, and the 2nd bedroom uses a hall bath. The...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,500 - $3,500
June 2027
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$2,500
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$2,500
27
28
29
30
 $3,000
July 2027
SuMoTuWeThFrSaWeek
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$3,000
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$3,000
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$3,000
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$3,000
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$3,000
August 2027
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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$3,500
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30
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 $2,500
September 2027
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$2,500
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$2,500
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30
 $2,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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Charming West Tisbury Country Setting, Access to Association Pool,, Mutiple Indoor/Outdoor Living Spaces, Gorgeous Private Yard

Spacious, light-filled home set in a lovely community with AC and a well-equipped kitchen. The sun room opens to the deck which overlooks a lovely, private yard.  A combined living and dining...Read more

Location: 
West Tisbury
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,600 - $3,500
June 2027
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July 2027
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
August 2027
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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 $2,600
September 2027
SuMoTuWeThFrSaWeek
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$2,600
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$2,600
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29
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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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:
$3,500 - $3,500
June 2027
SuMoTuWeThFrSaWeek
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$3,500
6
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$3,500
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$3,500
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21
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25
26
$4,000
27
28
29
30
 $5,800
July 2027
SuMoTuWeThFrSaWeek
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2
3
$5,800
4
5
6
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$5,800
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$5,800
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19
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$5,800
25
26
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$5,800
August 2027
SuMoTuWeThFrSaWeek
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$6,000
8
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$6,000
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$6,000
22
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$6,000
29
30
31
 $4,250
September 2027
SuMoTuWeThFrSaWeek
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$4,250
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$3,500
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$3,500
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$3,500
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 $3,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes

Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $3,500
June 2027
SuMoTuWeThFrSaWeek
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5
$3,500
6
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$3,500
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$3,500
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$3,800
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 $4,500
July 2027
SuMoTuWeThFrSaWeek
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$4,500
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$5,500
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$5,500
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$5,500
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$6,000
August 2027
SuMoTuWeThFrSaWeek
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$7,000
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$7,000
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$7,000
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$5,500
29
30
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 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,000
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 $3,500
Clean Fee: 
$575
Tax: State & Local: 
14.45

 

 

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Newly Updated Chilmark Cottage, Key to Private association Black Point Beach just 8/10ths mile from Cottage

For those who love Chilmark! Located in a very private setting off of Quenames Rd, this fresh and modern updated cottage comes with a key to private association Black Point...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$3,500 - $3,500
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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This luxuriously updated tri-level condo retreat at Quail Run in the community of homes known as Sengekontacket, has been transformed, bringing a fresh, coastal feel to every corner. The end...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$3,500 - $3,500
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$400 per week
Tax: State & Local: 
14.45
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SWEET 3-BEDROOM, 3-BATH CHILMARK COTTAGE, SPACIOUS SCREENED PORCH AND DECK AREAS, OUTDOOR SHOWER; PRIVATE LOCATION ON 4 ACRES, 10 MINUTES TO LUCY VINCENT AND LONG POINT BEACHES

Charming updated summer home features a dining room that seats six, well-stocked kitchen, living room, plus screen porch with ceiling fan, dining table and chairs for 8, and reading/lounging nooks, leading...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,300 - $3,300
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$400 per week, $150 interim cleaning on multiple week rentals
Tax: State & Local: 
11.7
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Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,200 - $3,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
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12
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14
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17
18
19
$3,200
20
21
22
23
24
25
26
$3,200
27
28
29
30
 $3,200
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,200
4
5
6
7
8
9
10
$3,200
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12
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$3,200
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19
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21
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23
24
$3,200
25
26
27
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29
30
31
$3,200
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,200
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11
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13
14
$3,200
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21
$3,200
22
23
24
25
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27
28
$3,200
29
30
31
 $3,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,200
5
6
7
8
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10
11
$3,200
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13
14
15
16
17
18
$3,200
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$360 per week
Tax: State & Local: 
14.45
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Menemsha, Water View, Walk to beach
Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,950 - $3,200
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$1,950
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7
8
9
10
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12
$1,950
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$1,950
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26
$1,950
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28
29
30
 $3,000
July 2027
SuMoTuWeThFrSaWeek
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2
3
$3,000
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5
6
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9
10
$3,000
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$3,000
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$3,000
25
26
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30
31
$3,000
August 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
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$3,200
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$3,200
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$3,200
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28
$3,200
29
30
31
 $3,200
September 2027
SuMoTuWeThFrSaWeek
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2
3
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$3,200
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Clean Fee: 
$200 per week
Tax: State & Local: 
11.7
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Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

MVVR EXCLUSIVE:  Classic, beach cottage with spectacular views across the sound, calm water swimming, and a great area for kayaking. The open kitchen, dining, and living areas are enhanced by the wall of windows...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
1
Price Range:
$1,900 - $3,200
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$2,250
6
7
8
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12
$2,300
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$2,700
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26
$2,900
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28
29
30
 $3,250
July 2027
SuMoTuWeThFrSaWeek
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2
3
$3,250
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5
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$3,250
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$3,250
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$3,250
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$3,350
August 2027
SuMoTuWeThFrSaWeek
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2
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$3,400
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$3,400
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$3,400
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$3,200
29
30
31
 $2,000
September 2027
SuMoTuWeThFrSaWeek
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3
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$2,000
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$2,000
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$2,000
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$2,000
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29
30
 
Clean Fee: 
$325 per week
Tax: State & Local: 
14.45

Cottage books Tuesday to Tuesday July & August weeks

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Dodger's Hole, Lovely Cape Style Home, Deck, Yard

Spacious 3 bedroom, 2.5 bath home nestled on a pine and treed 1/2 acre knoll.  House is approximately 2,000 sq. ft.  Separate living room, dining room and eat-in kitchen with...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,100 - $3,100
June 2027
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July 2027
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September 2027
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Central Location with Ease of Access to Village Centers and Multiple Beaches

Lovely vacation home budget-friendly in a quiet residential area and centrally located with a short drive to town centers of Oak Bluffs, Edgartown, and Vineyard Haven. Multiple Beaches 10 to 15-minute drive...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,200 - $3,100
June 2027
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$2,800
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 $2,800
July 2027
SuMoTuWeThFrSaWeek
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2
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$2,800
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$3,000
11
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$3,000
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$3,000
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$3,000
August 2027
SuMoTuWeThFrSaWeek
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$3,100
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$3,100
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$3,100
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$3,100
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 $2,500
September 2027
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$2,500
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$2,500
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 $2,500
Clean Fee: 
Included
Tax: State & Local: 
11.7
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Edgartown Village, Walk to Town Center, Large Deck and Farmers Porch for Outdoor Enjoyment

Walk to Village Area from this sweet, cape-style home that features a farmer's porch across the front and a 12 x 20 mahogany deck across the back with an enclosed outside shower. 

The...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $3,000
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
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CENTRAL KATAMA LOCATION, BIKE TO BEACH OR TOWN, LARGE, PRIVATE BACKYARD, Central A/C

Note: Not seen in the photos displayed, the kitchen has new stone counters and a new stainless stove. 

Wonderful three-bedroom, two-bath home offering unique Vineyard character with raised, beamed ceilings and...Read more

Location: 
Katama
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $3,000
June 2027
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July 2027
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August 2027
SuMoTuWeThFrSa
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$225 per week
Tax: State & Local: 
11.7

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