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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:
$3,000 - $5,000
June 2026
SuMoTuWeThFrSaWeek
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$3,000
14
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$3,000
21
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$3,500
28
29
30
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$5,000
5
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$5,000
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$4,000
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$4,000
26
27
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30
31
 $5,000
August 2026
SuMoTuWeThFrSaWeek
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$5,000
2
3
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$7,500
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$7,500
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$7,500
23
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$5,000
30
31
 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$4,500
6
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$4,500
13
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$3,500
20
21
22
23
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25
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$3,500
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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VANDN

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Property Details
Charming Newly Updated Menemsha Cottage, 2 + Bedroom Cottage Sleeps 5, AC, Screened Porch & Deck, Walk to Menemsha Village & Beach

Dreaming of Vacationing in an idyllic Menemsha Cottage? This adorable newly updated  1950s cottage nestled in the village area provides easy access to numerous exclusive Chilmark beaches with town permits and Menemsha Beach...Read more

Location: 
Chilmark
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$2,500 - $3,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
7
8
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10
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12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$3,000
28
29
30
 $3,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,500
5
6
7
8
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10
11
$3,500
12
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$3,500
19
20
21
22
23
24
25
$3,500
26
27
28
29
30
31
 $3,500
August 2026
SuMoTuWeThFrSaWeek
 1
$3,500
2
3
4
5
6
7
8
$3,500
9
10
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15
$3,500
16
17
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$3,500
23
24
25
26
27
28
29
$3,500
30
31
 $3,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
$3,200
6
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12
$3,200
13
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$3,200
20
21
22
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25
26
$3,200
27
28
29
30
 
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Owner will rent off weekend arrival and departure dates, weeks open in 2026, to accommodate the need for Auto ferry reservations. Inquire!

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VOL55

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Property Details
LIGHT FILLED CONTEMPORARY HOME, AC, DECK AND SUN PORCH, SLEEPS 8

Set on a quiet circular street (Teaberry Lane), on the outskirts of Edgartown. Bike paths at the end of the street connect to town and miles of touring trails. This...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$4,250 - $4,250
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
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12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 $3,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,200
5
6
7
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9
10
11
$3,200
12
13
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18
$4,150
19
20
21
22
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24
25
$4,150
26
27
28
29
30
31
 $4,150
August 2026
SuMoTuWeThFrSaWeek
 1
$4,150
2
3
4
5
6
7
8
$4,250
9
10
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12
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14
15
$4,250
16
17
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21
22
$4,250
23
24
25
26
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28
29
$4,250
30
31
 
September 2026
SuMoTuWeThFrSa
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27
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29
30
 
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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VOREA

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Property Details
Meeting House Village Condo, Association Pool, Short Drive to Edgartown Center, South Beach & State Beach

Note: Owner is replacing Sofas seen in photos with two new slip covered sofas and will be replacing all bedding and the baths will get a primp as well. New kitchen items...Read more

Location: 
Edgartown
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSa
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August 2026
SuMoTuWeThFrSa
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September 2026
SuMoTuWeThFrSa
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27
28
29
30
 
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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WALCN

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Property Details
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
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10
11
$5,770
12
13
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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
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7
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$6,470
9
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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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WALSB

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Property Details
Contemporary, Spacious Home, Heated Pool,18 x 40, Luxury Amenities, Screened Porch, Patio and Private Yard

This beautiful new luxury home with an 18 x 40 heated pool which is located a quick bike ride to Morning Glory Farm and close to historic Edgartown Village, is...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
6
Baths: 
4
Price Range:
$6,500 - $17,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$9,750
7
8
9
10
11
12
13
$10,750
14
15
16
17
18
19
20
$13,000
21
22
23
24
25
26
27
$15,000
28
29
30
 $17,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$17,000
5
6
7
8
9
10
11
$17,000
12
13
14
15
16
17
18
$17,000
19
20
21
22
23
24
25
$17,500
26
27
28
29
30
31
 $18,000
August 2026
SuMoTuWeThFrSaWeek
 1
$18,000
2
3
4
5
6
7
8
$18,500
9
10
11
12
13
14
15
$18,500
16
17
18
19
20
21
22
$18,500
23
24
25
26
27
28
29
$16,000
30
31
 $8,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,500
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$6,750
27
28
29
30
 $6,500
Clean Fee: 
$675 per week
Tax: State & Local: 
11.7

Ferry Tickets Available for purchase 6/27(1:40)-7/4(12) (o) - please inquire

 

Pool is heated to 82 degrees in July and August included in rental rate. 

 

Pool heat fee May, June, Sept $350 per week. Pool heated to 82. 

Pool is not available after October 5th

 

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WALSJ

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Property Details
Gorgeous in Town Home, Heated Saltwater Pool, 16 x 32, Pool Cabana/Office Space, 5 minute walk to the heart of Edgartown Village

Sansouci  Located on a quiet cul de sac that is a 5-minute walk to restaurants and shops in downtown Edgartown. It’s a 10-minute walk to the harbor and a 15-minute walk...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$20,000 - $23,000
June 2026
SuMoTuWeThFrSa
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2
3
4
5
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July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
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13
14
15
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17
18
$20,000
19
20
21
22
23
24
25
$20,000
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$23,000
9
10
11
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13
14
15
$23,000
16
17
18
19
20
21
22
$23,000
23
24
25
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27
28
29
$23,000
30
31
 
September 2026
SuMoTuWeThFrSa
 1
2
3
4
5
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9
10
11
12
13
14
15
16
17
18
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20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Ferry Tickets available 7/11-7/18, 7/18-7/25, 8/22-8/29 - please inquire

 

Pool heated to 82 in July & August included in the rental rate. 

Pool heated to 82 in June & September additional $250 per week, May & October additional $350 per week 
 

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WALSP

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Property Details
Gracious Village Area 5 Bedroom Home, Light Filled Interior, Mulitple Living Spaces, Large Landscaped Yard, Located on Quiet Side St, 5 min Walk to Main St.

Stunning Edgartown Village Home! This meticulously maintained and newly updated property offers multiple living areas, 5 bedrooms, and 3.5 baths, surrounded by a lushly landscaped yard. Just a 5-minute walk...Read more

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

 

Parking for 3 cars, no on street parking

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WASHS

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Property Details
Stylish and Beautifully Decorated Summer Residence, Screened Porch, Spacious Deck, WiFi

Centrally located mid-island, this beautifully appointed home features an open design kitchen, dining, and living areas for easy entertaining with family and friends.  French doors off of the living area...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,350
7
8
9
10
11
12
13
$2,350
14
15
16
17
18
19
20
$2,350
21
22
23
24
25
26
27
$3,700
28
29
30
 $4,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,200
5
6
7
8
9
10
11
$4,200
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$4,500
9
10
11
12
13
14
15
$4,500
16
17
18
19
20
21
22
$4,500
23
24
25
26
27
28
29
$4,500
30
31
 
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$2,350
13
14
15
16
17
18
19
$2,350
20
21
22
23
24
25
26
$2,350
27
28
29
30
 $2,100
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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WATTL

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

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