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SPACIOUS LIGHTFILLED 3 BEDROOM, 3 BATH HOME, PRIVATE DECK WITH PATIO DINING, 7 MINUTE DRIVE TO THE CENTER OF OAK BLUFFS AND INKWELL BEACH

Experience the best of Island living—peaceful residential surroundings, the vibrant shops and attractions of the three Down Island towns (Oak Bluffs, Edgartown, and Vineyard Haven), and quick access to public...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$2,700 - $5,500
June 2027
SuMoTuWeThFrSaWeek
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3
4
5
$3,900
6
7
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10
11
12
$3,900
13
14
15
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17
18
19
$3,900
20
21
22
23
24
25
26
$4,300
27
28
29
30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
4
5
6
7
8
9
10
$4,500
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12
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$4,500
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19
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24
$4,500
25
26
27
28
29
30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
6
7
$5,500
8
9
10
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12
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14
$5,500
15
16
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18
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20
21
$5,500
22
23
24
25
26
27
28
$5,500
29
30
31
 $5,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,200
5
6
7
8
9
10
11
$3,700
12
13
14
15
16
17
18
$3,200
19
20
21
22
23
24
25
$3,200
26
27
28
29
30
 $3,200
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

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Beautiful Newly Updated Cape Style Home, Association Tennis Courts 2 min Walk, Biking & Hiking Trails, Beaches 10 minutes from House

This lovely 3 bedroom, 2.5 bath home features sun-filled rooms, an open floor plan throughout, screened porch set up as a summer living room with a sectional sofa, and a...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,000 - $5,400
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
Tax: State & Local: 
11.7
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Charming Katama Cape Style Home, Screened Porch with Dining, Deck and Farmers Porch, 3 minute drive to South Beach and 5 minute drive to Edgartown Village

A charming Katama home, set equidistance, 1.5 miles, between South Beach and Edgartown Village Center. 

Multiple outdoor areas include a farmer's porch with rockers, a spacious screened porch with outdoor dining...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$2,200 - $5,300
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,800
6
7
8
9
10
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12
$2,800
13
14
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18
19
$3,750
20
21
22
23
24
25
26
$3,750
27
28
29
30
 $5,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,000
4
5
6
7
8
9
10
$5,000
11
12
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16
17
$5,300
18
19
20
21
22
23
24
$5,300
25
26
27
28
29
30
31
$5,300
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,300
8
9
10
11
12
13
14
$5,300
15
16
17
18
19
20
21
$4,800
22
23
24
25
26
27
28
$4,800
29
30
31
 $4,800
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,800
5
6
7
8
9
10
11
$3,800
12
13
14
15
16
17
18
$2,200
19
20
21
22
23
24
25
$2,200
26
27
28
29
30
 $2,200
Clean Fee: 
$450
Tax: State & Local: 
11.7
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Charming & Cozy 2 Bedroom, 2 Bath Home, West Chop area of Vineyard Haven, Located on a Quiet Street, Close to Town & Beach

Note: Newly completed, not seen in photos, a 250 square foot deck has been added to the back of the house. The deck will have a patio dining table, and...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,450 - $5,150
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,850
6
7
8
9
10
11
12
$3,850
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,850
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,850
4
5
6
7
8
9
10
$4,850
11
12
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14
15
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17
$4,850
18
19
20
21
22
23
24
$4,850
25
26
27
28
29
30
31
$5,150
August 2027
SuMoTuWeThFrSaWeek
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2
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7
$5,150
8
9
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14
$5,150
15
16
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21
$5,150
22
23
24
25
26
27
28
$5,150
29
30
31
 $5,150
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$5,150
5
6
7
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$3,250
12
13
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18
$3,250
19
20
21
22
23
24
25
$3,250
26
27
28
29
30
 $3,250
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Vineyard Meadow Farms Home, Close to Gorgeous Long Point Beach, Contemporary Styling, Central AC, Wi-Fi, Private Yard and Deck

 

 Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,400 - $5,100
June 2027
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
$4,900
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
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17
$4,900
18
19
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23
24
$4,900
25
26
27
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30
31
$5,100
August 2027
SuMoTuWeThFrSaWeek
1
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$5,100
8
9
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$5,100
15
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$5,100
22
23
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25
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27
28
$4,900
29
30
31
 $4,900
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
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$4,900
5
6
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$4,400
12
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$4,400
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24
25
$4,400
26
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,

Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $5,000
June 2027
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
 $4,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,000
4
5
6
7
8
9
10
$5,000
11
12
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17
$4,500
18
19
20
21
22
23
24
$4,500
25
26
27
28
29
30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
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5
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7
$7,500
8
9
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$7,500
15
16
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21
$7,500
22
23
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31
 $4,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
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$4,500
5
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$4,500
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$3,500
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20
21
22
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24
25
$3,500
26
27
28
29
30
 $3,500
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

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

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Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Great Area for Kayaking.

Spacious sun-filled home features open living spaces, hardwood floors throughout, 4 bedrooms and sleeps 8.

Exterior features include two decks, one sunny deck at the front of the house, and a large private...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,000 - $5,000
June 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$480 per week
Tax: State & Local: 
11.7
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Hidden Cove Retreat, Walk to Association Tennis/Pickleball Courts, 3 Bedrooms, 2.5 Baths, Screened Porch and Deck

Nestled in the charming Hidden Cove community, this adorable contemporary home resides on a tranquil street within walking distance of the association's tennis/pickleball courts. Its central location places it just a...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $5,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
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21
22
23
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25
26
27
28
29
30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
4
5
6
7
8
9
10
$4,500
11
12
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$4,500
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19
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21
22
23
24
$4,500
25
26
27
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29
30
31
$5,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,000
8
9
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12
13
14
$5,000
15
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$5,000
22
23
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28
$4,500
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
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$4,000
5
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Multiple Living Spaces, Screened Porch, Spacious Deck, AC, Wifi, Beautifully Furnished, Bike Paths at the head of the Road

Spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. . The main living level features an open concept and hosts a family...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,700 - $5,000
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: 
$500 per week ($375 for interim cleaning on multiple week rentals)
Tax: State & Local: 
11.7
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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:
$3,000 - $5,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
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9
10
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12
$3,500
13
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17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
4
5
6
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10
$4,500
11
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$4,500
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19
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23
24
$4,500
25
26
27
28
29
30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,000
8
9
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14
$5,000
15
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20
21
$5,000
22
23
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25
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27
28
$5,000
29
30
31
 $4,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,500
5
6
7
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10
11
$4,250
12
13
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18
$3,500
19
20
21
22
23
24
25
$3,500
26
27
28
29
30
 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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Lovely Oak Bluffs Home, 3 Bedrooms, 2.5 Baths, Sleeps 7. Set just on the Outskirts of Oak Bluffs Center

Lovely 3 bedroom, 2.5 bath home that sleeps 7. This sweet home is bordered by a large yard and is located just on the outskirts of Oak Bluffs. The patio...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$2,000 - $5,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $4,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,800
4
5
6
7
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9
10
$4,800
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$4,800
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$4,800
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30
31
$4,800
August 2027
SuMoTuWeThFrSaWeek
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2
3
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5
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7
$5,000
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$5,000
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$5,000
22
23
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25
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27
28
$5,000
29
30
31
 $4,500
September 2027
SuMoTuWeThFrSaWeek
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2
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4
$4,500
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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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 - $5,000
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: 
$400 per week
Tax: State & Local: 
11.7
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Charming, 4-bedroom Oak Bluffs Home, pristinely maintained!  The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,000 - $5,000
June 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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 $5,000
July 2027
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$5,000
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$5,000
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$5,000
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$5,000
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$5,000
August 2027
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$5,000
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$5,000
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$5,000
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$5,000
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 $4,000
September 2027
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$4,000
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$2,000
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$2,000
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$2,000
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 $2,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Parking for two cars only, no on-street parking!

 

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Edgartown Village Center Home, Walk to Town, 2 Bedrooms, 2 Baths

Experience all that Edgartown Village Center has to offer, just a short stroll from this bright and airy home. Additional décor and deck furniture will be added for summer 2025....Read more

Location: 
Edgartown
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$4,000 - $5,000
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: 
$350 per week
Tax: State & Local: 
11.7
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"Endless Summer Vacation" Stylish, Newly Updated 3 + Bedroom, Sleeps 8, East Chop Area of Oak Bluffs, Deck Living & Dining Area, Screened Porch
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $5,000
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: 
$450 per week
Tax: State & Local: 
11.7

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