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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:
$1,700 - $3,500
June 2025
SuMoTuWeThFrSaWeek
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 $2,700
July 2025
SuMoTuWeThFrSaWeek
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$2,700
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$2,700
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$2,700
20
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$2,800
27
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31
 $3,000
August 2025
SuMoTuWeThFrSaWeek
 1
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$3,000
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$3,000
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$3,000
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$3,000
24
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$2,600
31
 $1,700
September 2025
SuMoTuWeThFrSaWeek
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$1,700
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$1,700
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$1,700
21
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27
$1,700
28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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WE122

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Property Details
Luxury Modern Farm House Design, Waterfront Pear Tree Cove on the Tisbury Great Pond, Rental Boat Access to South Shore Beach, Spectacular Area for Kayak Enthusiasts

New exquisite contemporary farmhouse design! Waterfront on the Tisbury Great Pond with access via boat rentals to gorgeous South Shore Beach. The beach area on the pond provides a great play space...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$9,500 - $9,500
June 2025
SuMoTuWeThFrSaWeek
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26
27
28
29
30
 $12,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$12,500
6
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$12,500
13
14
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$14,500
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21
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$14,500
27
28
29
30
31
 $14,500
August 2025
SuMoTuWeThFrSaWeek
 1
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$14,500
3
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$14,500
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$14,500
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$14,500
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29
30
$14,500
31
 $9,500
September 2025
SuMoTuWeThFrSaWeek
 1
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$9,500
7
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$9,500
14
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$9,500
21
22
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27
$9,500
28
29
30
 $9,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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WEBSL

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Property Details
Menemsha

Magical Menemsha Cottage with water views of the Elizabeth Islands and harbor. The wooded property encompasses 3 private acres and is within walking distance to the village of Menemsha and...Read more

Location: 
Chilmark
Sleeps: 
7
Bedrooms: 
3
Baths: 
1
Price Range:
$3,520 - $6,030
June 2025
SuMoTuWeThFrSaWeek
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29
30
 $7,000
July 2025
SuMoTuWeThFrSaWeek
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$7,000
6
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$7,000
13
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$7,000
20
21
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$7,000
27
28
29
30
31
 $8,220
August 2025
SuMoTuWeThFrSaWeek
 1
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$8,220
3
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$8,220
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$8,220
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$8,220
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$8,220
31
 $6,030
September 2025
SuMoTuWeThFrSaWeek
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$6,030
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$6,030
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$6,030
21
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$6,030
28
29
30
 $4,050
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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WEEKW

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Property Details
CLASSIC, IN-TOWN EDGARTOWN, ENGLISH-COUNTRY CHIC LUXURY HOME WITH POOL AND MANICURED GROUNDS

Exquisite home in the village of Edgartown that exudes classic taste with English-Country styling.  This in-town location makes it easy to stroll down to dinner on the harbor or walk...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
7
Baths: 
6
Price Range:
$10,500 - $29,500
June 2025
SuMoTuWeThFrSaWeek
1
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30
 $29,500
July 2025
SuMoTuWeThFrSaWeek
 1
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$29,500
6
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12
$29,500
13
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19
$29,500
20
21
22
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24
25
26
$29,500
27
28
29
30
31
 $29,500
August 2025
SuMoTuWeThFrSaWeek
 1
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$29,500
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31
 $12,500
September 2025
SuMoTuWeThFrSaWeek
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$12,500
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$10,500
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20
$10,500
21
22
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26
27
$10,500
28
29
30
 $10,500
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7
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WEI33

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Property Details
Stunning, Charming, Historic Luxury Home in Edgartown Village Center, Newly Remodeled,

This beautifully remodeled historic home is nestled in the heart of Edgartown Village and boasts 4 bedrooms and 4.5 luxurious baths, complete with an array of inviting indoor and outdoor...Read more

Location: 
Edgartown
Bedrooms: 
5
Baths: 
4
Price Range:
$8,000 - $19,000
June 2025
SuMoTuWeThFrSaWeek
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 $19,000
July 2025
SuMoTuWeThFrSaWeek
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$19,000
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$15,000
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$15,000
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$15,000
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 $19,000
August 2025
SuMoTuWeThFrSaWeek
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$19,000
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September 2025
SuMoTuWeThFrSa
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21
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25
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27
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29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Rates just reduced on available weeks in July - see calendar for adjusted rates

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WEINS

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Property Details
Charming and Pristine Hilltop Restored Farm House, Water views, Spectacular Sunsets, Set on Large Private Acreage

Hilltop House is located on one of the highest points on the Island displaying broad views across the rolling hills to beautiful water views beyond. Acres of undisturbed privacy and a...Read more

Location: 
Aquinnah
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$6,800 - $6,800
June 2025
SuMoTuWeThFrSa
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July 2025
SuMoTuWeThFrSaWeek
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$6,800
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31
 $6,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,800
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$6,800
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$6,800
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$6,800
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27
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29
30
$6,800
31
 $6,800
September 2025
SuMoTuWeThFrSaWeek
 1
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$6,800
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10
11
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14
15
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21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Two-week minimum stay required!

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WEISM

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Property Details
Outstanding Tri -Level Katama Home, Pool, new 18 x 40 Heated Saltwater Pool, Bluestone Patio, Fire Pit, Walk or Bike to South Beach and 5 minute Drive to Edgartown Village Area

Beautiful tri-level contemporary home with an 18 x 40 heated saltwater pool, bluestone patio, outdoor dining area, chaise lounge chairs, and fire pit. This recently updated home includes a spacious open floor plan with vaulted ceilings, a...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
4
Baths: 
4
Price Range:
$7,500 - $17,500
June 2025
SuMoTuWeThFrSaWeek
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 $17,500
July 2025
SuMoTuWeThFrSaWeek
 1
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3
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5
$17,500
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$17,500
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$17,500
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21
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$17,500
27
28
29
30
31
 $18,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$18,000
3
4
5
6
7
8
9
$18,000
10
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$18,000
17
18
19
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21
22
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$18,000
24
25
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27
28
29
30
$16,990
31
 $9,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$9,800
7
8
9
10
11
12
13
$9,200
14
15
16
17
18
19
20
$7,500
21
22
23
24
25
26
27
$7,500
28
29
30
 
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

 Transferable Ferry Tickets available, 8/23-8/30

 

Pool is heated to 84 degrees July & August &  included in the rental rate.

 

Pool heated to 84 degrees June & September, additional $450/week propane surcharge.

 

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WESTC

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Property Details
Summer Wind in the Heart of Oak Bluffs, Water views. 2 minute Walk to Inkwell Beach & 5 minute walk to town, All Newly Remodeled 5 Bedroom, 3 Bath Home With Deluxe Amenities

Set in the heart of Oak Bluffs center, this newly renovated home features water views, walk to Inkwell Beach and Pay Beach and walk to the town center all within...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$6,000 - $17,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
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17
18
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20
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27
28
29
30
 $12,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,000
6
7
8
9
10
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12
$12,000
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14
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18
19
$12,000
20
21
22
23
24
25
26
$13,000
27
28
29
30
31
 $16,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$16,000
3
4
5
6
7
8
9
$17,000
10
11
12
13
14
15
16
$17,000
17
18
19
20
21
22
23
$17,000
24
25
26
27
28
29
30
$9,000
31
 $8,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,000
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$7,000
28
29
30
 $6,000
Clean Fee: 
$550
Tax: State & Local: 
11.7
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WESTD

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Property Details
Deep Bottom Custom Contemporary, Heated Pool, Association Tennis Courts, Features Multiple Living Spaces on 3 Levels, A/C WiFi

Custom crafted contemporary home set on lush professionally landscaped grounds. The pool and patio area overlook the large yard with expansive views of the common meadows. There are private association...Read more

Location: 
West Tisbury
Sleeps: 
9
Bedrooms: 
6
Baths: 
4
Price Range:
$8,500 - $12,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
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20
21
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24
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26
27
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29
30
 $12,100
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,100
6
7
8
9
10
11
12
$12,100
13
14
15
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18
19
$12,100
20
21
22
23
24
25
26
$12,100
27
28
29
30
31
 $12,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$12,500
3
4
5
6
7
8
9
$12,500
10
11
12
13
14
15
16
$12,500
17
18
19
20
21
22
23
$12,500
24
25
26
27
28
29
30
$11,500
31
 $9,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$9,000
7
8
9
10
11
12
13
$9,000
14
15
16
17
18
19
20
$9,000
21
22
23
24
25
26
27
$9,000
28
29
30
 $9,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Pool heated to 81 July & August included in rental rate.

Pool heated to 81 June & September additional $275 per week 

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WESTW

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Property Details
Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
5
Baths: 
2
Price Range:
$5,000 - $12,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
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23
24
25
26
27
28
29
30
 $8,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$9,000
13
14
15
16
17
18
19
$9,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
31
 $10,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$10,000
3
4
5
6
7
8
9
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$12,000
24
25
26
27
28
29
30
$8,500
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
$5,000
28
29
30
 $5,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

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