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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 2026
SuMoTuWeThFrSaWeek
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$4,000
28
29
30
 $5,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$5,750
5
6
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$5,750
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$5,750
19
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$5,750
26
27
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30
31
 $5,750
August 2026
SuMoTuWeThFrSaWeek
 1
$5,750
2
3
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$6,000
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$6,000
16
17
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$6,000
23
24
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27
28
29
$6,000
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
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12
$5,000
13
14
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16
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18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 $3,500
Clean Fee: 
$400 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 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
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$4,000
28
29
30
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
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11
$5,000
12
13
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17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
4
5
6
7
8
$7,500
9
10
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12
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$7,500
16
17
18
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21
22
$7,500
23
24
25
26
27
28
29
$7,500
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
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10
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12
$5,000
13
14
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19
$5,000
20
21
22
23
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25
26
$5,000
27
28
29
30
 $5,000
Clean Fee: 
$450 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 - $5,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
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12
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20
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24
25
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27
$4,000
28
29
30
 $5,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
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10
11
$5,000
12
13
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18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
4
5
6
7
8
$6,000
9
10
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12
13
14
15
$6,000
16
17
18
19
20
21
22
$5,750
23
24
25
26
27
28
29
$5,000
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$4,000
6
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$3,500
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19
$3,500
20
21
22
23
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25
26
$3,500
27
28
29
30
 $3,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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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 - $4,990
June 2026
SuMoTuWeThFrSaWeek
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$5,530
28
29
30
 $7,090
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,090
5
6
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10
11
$7,090
12
13
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15
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18
$7,090
19
20
21
22
23
24
25
$7,090
26
27
28
29
30
31
 $7,090
August 2026
SuMoTuWeThFrSaWeek
 1
$7,090
2
3
4
5
6
7
8
$7,090
9
10
11
12
13
14
15
$7,090
16
17
18
19
20
21
22
$7,090
23
24
25
26
27
28
29
$6,560
30
31
 $6,040
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,040
6
7
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9
10
11
12
$5,510
13
14
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17
18
19
$4,990
20
21
22
23
24
25
26
$4,990
27
28
29
30
 $4,460
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Note: Older style TVs seen in photos have been replaced. 

This bright and classic summer cottage is ideally located just one mile from Oak Bluffs town center and all the...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$4,000 - $4,950
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
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12
13
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22
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$4,000
28
29
30
 
July 2026
SuMoTuWeThFrSaWeek
 1
2
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30
31
 $4,950
August 2026
SuMoTuWeThFrSaWeek
 1
$4,950
2
3
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$4,950
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$4,950
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$4,950
23
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29
$4,950
30
31
 $4,000
September 2026
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
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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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:
$2,200 - $4,900
June 2026
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
$3,220
28
29
30
 $4,350
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,350
5
6
7
8
9
10
11
$4,350
12
13
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17
18
$4,350
19
20
21
22
23
24
25
$4,350
26
27
28
29
30
31
 $4,750
August 2026
SuMoTuWeThFrSaWeek
 1
$4,750
2
3
4
5
6
7
8
$4,850
9
10
11
12
13
14
15
$4,850
16
17
18
19
20
21
22
$4,850
23
24
25
26
27
28
29
$4,400
30
31
 $3,100
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,100
6
7
8
9
10
11
12
$3,100
13
14
15
16
17
18
19
$2,700
20
21
22
23
24
25
26
$2,200
27
28
29
30
 $2,200
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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1.5 Acres of Privacy, Bike Paths Adjacent to House, Association Pool, WiFi, Central A/C

West Tisbury - Newly updated and featuring 5 bedrooms and 4 baths.  Recently renovated including all new kitchen, updated baths, flooring, carpeting, walls painted, and lovely furnishings.  There is central AC on the 1st...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$3,900 - $4,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
$3,500
28
29
30
 $5,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,900
5
6
7
8
9
10
11
$6,250
12
13
14
15
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17
18
$6,250
19
20
21
22
23
24
25
$6,500
26
27
28
29
30
31
 $6,500
August 2026
SuMoTuWeThFrSaWeek
 1
$6,500
2
3
4
5
6
7
8
$6,500
9
10
11
12
13
14
15
$6,500
16
17
18
19
20
21
22
$6,500
23
24
25
26
27
28
29
$6,500
30
31
 $5,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,900
6
7
8
9
10
11
12
$4,900
13
14
15
16
17
18
19
$4,900
20
21
22
23
24
25
26
$4,900
27
28
29
30
 $3,900
Clean Fee: 
$450 per week, $600 per week with pet
Tax: State & Local: 
11.7
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Newly Remodeled Contemporary Farm House, 12 x 26 Saltwater Heated Pool, Walk to Town, Bike to the Beach

Exquisite newly remodeled home with just the right touch of coastal decor and modern styling. This perfectly situated picturesque home allows guests to walk to the village area and is an easy no...Read more

Location: 
Katama
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,200 - $4,900
June 2026
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
$9,300
28
29
30
 $9,300
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,300
5
6
7
8
9
10
11
$9,300
12
13
14
15
16
17
18
$9,920
19
20
21
22
23
24
25
$9,920
26
27
28
29
30
31
 $10,400
August 2026
SuMoTuWeThFrSaWeek
 1
$10,400
2
3
4
5
6
7
8
$10,400
9
10
11
12
13
14
15
$10,400
16
17
18
19
20
21
22
$10,400
23
24
25
26
27
28
29
$7,200
30
31
 $6,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$4,900
20
21
22
23
24
25
26
$4,500
27
28
29
30
 $4,200
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Pool heated to 81 in July & August included in rental rate.  Additional $250 per week in off season.

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Lovely Contemporary Home, Quiet Location in Pond View, Private Back Yard, Porch & Deck

Beautifully maintained, family-friendly home.

Lovely 3 Bedroom, 2.5 bath home situated in a quiet enclave of homes known as Pond View and just 2.5 miles to the center of Oak Bluffs....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,700 - $4,900
June 2026
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
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
7
8
9
10
11
$4,700
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
31
 $4,900
August 2026
SuMoTuWeThFrSaWeek
 1
$4,900
2
3
4
5
6
7
8
9
10
11
12
13
14
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September 2026
SuMoTuWeThFrSa
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12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Lovely Home in Island Grove Area of Edgartown Conveniently Located between South Beach and Edgartown Village. Association Tennis Courts and Pickleball Available to Renters

This recently updated home is tucked in the Island Grove area of Edgartown and is a perfect retreat for families & friends to gather. Located in a desirable neighborhood with access...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,800 - $4,800
June 2026
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
$4,800
28
29
30
 $5,280
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,280
5
6
7
8
9
10
11
$5,770
12
13
14
15
16
17
18
$5,770
19
20
21
22
23
24
25
$5,770
26
27
28
29
30
31
 $5,770
August 2026
SuMoTuWeThFrSaWeek
 1
$5,770
2
3
4
5
6
7
8
$6,470
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$4,800
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$525 per week
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 - $4,800
June 2026
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
$4,800
28
29
30
 $5,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,400
5
6
7
8
9
10
11
$5,400
12
13
14
15
16
17
18
$5,400
19
20
21
22
23
24
25
$5,400
26
27
28
29
30
31
 $5,800
August 2026
SuMoTuWeThFrSaWeek
 1
$5,800
2
3
4
5
6
7
8
$5,800
9
10
11
12
13
14
15
$5,800
16
17
18
19
20
21
22
$5,800
23
24
25
26
27
28
29
$5,800
30
31
 $4,800
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,800
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
$3,600
27
28
29
30
 $3,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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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 - $4,800
June 2026
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
$4,200
28
29
30
 $4,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,500
5
6
7
8
9
10
11
$4,500
12
13
14
15
16
17
18
$4,500
19
20
21
22
23
24
25
$4,500
26
27
28
29
30
31
 $4,800
August 2026
SuMoTuWeThFrSaWeek
 1
$4,800
2
3
4
5
6
7
8
$4,800
9
10
11
12
13
14
15
$4,800
16
17
18
19
20
21
22
$4,800
23
24
25
26
27
28
29
$4,800
30
31
 $3,000
September 2026
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
$3,000
27
28
29
30
 $3,000
Clean Fee: 
$225 per week
Tax: State & Local: 
11.7

Ferry Tickets Available for purchase 7/19-7/26, & 7/26-8/2 - please inquire

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Waterfront, Water View, Walk to Beach

Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $4,700
June 2026
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
$3,700
28
29
30
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
7
8
9
10
11
$4,700
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
31
 $4,700
August 2026
SuMoTuWeThFrSaWeek
 1
$4,700
2
3
4
5
6
7
8
$4,700
9
10
11
12
13
14
15
$4,700
16
17
18
19
20
21
22
$4,700
23
24
25
26
27
28
29
$4,700
30
31
 $4,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,700
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
Clean Fee: 
$300 per week, owner will provide sheets, towels, beach towels, additional $225 per rental period
Tax: State & Local: 
11.7

Owner will provide, sheets, towels & beach towels for an additional $225 per rented period. 

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Located in the Heart of Oak Bluffs, 5 Minute Walk to OB Center and 2 Blocks to the Beach
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
2
Price Range:
$2,000 - $4,700
June 2026
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
$4,300
28
29
30
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
7
8
9
10
11
$4,700
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
31
 $4,700
August 2026
SuMoTuWeThFrSaWeek
 1
$4,700
2
3
4
5
6
7
8
$4,700
9
10
11
12
13
14
15
$4,700
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 $4,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,100
13
14
15
16
17
18
19
$3,900
20
21
22
23
24
25
26
$3,300
27
28
29
30
 $2,700
Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
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Nicely Updated 4 bedroom Edgartown Home, Location 1.5 mi From Village Center, 10 minute Drive to Beaches. Miles of Bike Paths Nearby

Perfect family vacation home tucked on the outskirts of Edgartown just 1.5 miles to the village center and a 10-minute drive to South Beach and State Beach, and for those...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,700 - $4,650
June 2026
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
$3,700
28
29
30
 $4,650
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,650
5
6
7
8
9
10
11
$4,650
12
13
14
15
16
17
18
$4,650
19
20
21
22
23
24
25
$4,650
26
27
28
29
30
31
 $4,650
August 2026
SuMoTuWeThFrSaWeek
 1
$4,650
2
3
4
5
6
7
8
$4,700
9
10
11
12
13
14
15
$4,700
16
17
18
19
20
21
22
$4,700
23
24
25
26
27
28
29
$3,900
30
31
 $2,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,900
6
7
8
9
10
11
12
$2,700
13
14
15
16
17
18
19
$2,700
20
21
22
23
24
25
26
$2,700
27
28
29
30
 $2,700
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7

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