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Stately Historic Chilmark Home, All Newly updated to Luxury Standards, Private Association South Shore Beach Rights, Hancock Beach 1.5 miles from House

This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach!  The house lies between West Tisbury (Alley’s General Store, 7A...Read more

Location: 
Chilmark
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,000 - $13,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
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$8,000
6
7
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12
$8,000
13
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$8,000
20
21
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25
26
$8,000
27
28
29
30
 $11,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,000
4
5
6
7
8
9
10
$11,000
11
12
13
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$11,000
18
19
20
21
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23
24
$11,000
25
26
27
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29
30
31
$13,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
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5
6
7
$13,000
8
9
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$13,000
15
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$13,000
22
23
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26
27
28
$11,000
29
30
31
 $8,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,000
5
6
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10
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$8,000
12
13
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$8,000
19
20
21
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23
24
25
$8,000
26
27
28
29
30
 $5,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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BAKE7

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Property Details
Waterview, Walk to the Beach and Town Center, Impeccably Maintained 4 bedroom Home set in the Heart of Oak Bluffs.

This restored historic J.A. Norton Main and Guest Suite Quarters seamlessly blends 1870s character with the modern comforts today’s travelers appreciate. Nestled in a peaceful  Oak Bluffs neighborhood, the property is just...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,500 - $13,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
6
7
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10
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12
$7,000
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18
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$7,000
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25
26
$7,000
27
28
29
30
 $7,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,000
4
5
6
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10
$13,000
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12
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$13,000
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19
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$13,000
25
26
27
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30
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$13,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$15,000
8
9
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$15,000
15
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18
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$15,000
22
23
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25
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27
28
$15,000
29
30
31
 $10,500
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$10,500
5
6
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$6,500
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18
$5,500
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20
21
22
23
24
25
$5,500
26
27
28
29
30
 $5,500
Clean Fee: 
$400 per week
Tax: State & Local: 
14.45
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SHAJO~

Inquire
Property Details
Vineyard Haven, Walk to Main St, Lovely Victorian, Recently updated

Step into this exquisite Victorian-style residence, meticulously renovated to preserve its original allure while offering a sanctuary away from the bustle of everyday life. Nestled in the picturesque town of...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,500 - $13,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
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10
11
12
$6,000
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $9,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,500
4
5
6
7
8
9
10
$9,500
11
12
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14
15
16
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$9,500
18
19
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21
22
23
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$9,500
25
26
27
28
29
30
31
$13,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,000
8
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14
$13,000
15
16
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18
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20
21
$13,000
22
23
24
25
26
27
28
$12,000
29
30
31
 $8,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,000
5
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$8,000
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$5,500
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20
21
22
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24
25
$5,500
26
27
28
29
30
 $5,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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BROWJ~

Inquire
Property Details
Quintessential Edgartown Village Home, Impeccably Maintained, 3 Minute Walk to Main St, 8 Minute Walk to Lighthouse Beach & the Harborfront Area

Charming Historic Home in the Heart of Edgartown Village

Built in 1780 and thoughtfully updated, this beautifully maintained historic home blends timeless character with modern comforts. Ideally located in the...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $12,900
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$9,000
6
7
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$9,000
13
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$9,000
20
21
22
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24
25
26
$9,000
27
28
29
30
 $12,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$12,900
4
5
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9
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$12,900
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12
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31
August 2027
SuMoTuWeThFrSa
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September 2027
SuMoTuWeThFrSaWeek
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$9,000
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$9,000
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20
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24
25
$9,000
26
27
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29
30
 $9,000
Clean Fee: 
$500
Tax: State & Local: 
11.7

 

 

 

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SHAN2

Inquire
Property Details
Newly Updated Vacation Home, Katama Area of Edgartown, 12 x 30' Heated Pool, 4 Bedrooms, 4.5 Baths, Separate Recreation Barn with Ping Pong Table, Large Screen TV and Game Area, Bike Path to Village Center and to South Beach

Outstanding, modern farmhouse design, with heated pool and additional entertainment barn with ping-pong table, game table, game board games, and large screened TV just a few steps across the yard....Read more

Location: 
Katama
Sleeps: 
12
Bedrooms: 
4
Baths: 
4
Price Range:
$7,350 - $12,650
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,350
6
7
8
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12
$8,920
13
14
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$11,020
20
21
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$12,650
27
28
29
30
 $13,650
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$13,650
4
5
6
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9
10
$13,650
11
12
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$13,650
18
19
20
21
22
23
24
$14,700
25
26
27
28
29
30
31
$15,220
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$15,220
8
9
10
11
12
13
14
$15,220
15
16
17
18
19
20
21
$15,220
22
23
24
25
26
27
28
$10,500
29
30
31
 $8,920
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,920
5
6
7
8
9
10
11
$7,350
12
13
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15
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17
18
$7,350
19
20
21
22
23
24
25
$7,350
26
27
28
29
30
 $7,350
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees July & August included in rental rates. 

Pool heat is an additional $250 May, June, September, October

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PIN15

Inquire
Property Details
Beautiful Oak Bluffs Home, Screened Porch & Open Porch, Association Tennis Courts, 4 bedrooms, 3.5 baths, Ideally Located just 2 miles to Town and Beach

Spacious contemporary home nestled in the lovely community of homes Meadow View Farms just on the outskirts of Oak Bluffs and 2 miles to town center and Oak Bluffs beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$8,000 - $12,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
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18
19
20
21
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25
26
$9,000
27
28
29
30
 $9,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,000
4
5
6
7
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9
10
$9,000
11
12
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$9,000
18
19
20
21
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23
24
$12,500
25
26
27
28
29
30
31
$12,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,500
8
9
10
11
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13
14
$12,500
15
16
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18
19
20
21
$12,500
22
23
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25
26
27
28
$12,500
29
30
31
 $12,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,500
5
6
7
8
9
10
11
$12,500
12
13
14
15
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17
18
$8,500
19
20
21
22
23
24
25
$8,500
26
27
28
29
30
 $8,500
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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KOR30~

Inquire
Property Details
Sophisticated New Contemporary Home, Walk to Lambert's Cove Beach, Multiple Indoor Outdoor Living Spaces, Privately Tucked in Longview Area of West Tisbury

Discover a captivating modern retreat in the heart of West Tisbury on Martha’s Vineyard. Newly built and thoughtfully designed, this striking home blends clean architectural lines with contemporary comfort, offering...Read more

Location: 
West Tisbury
Sleeps: 
7
Bedrooms: 
3
Baths: 
3
Price Range:
$4,000 - $12,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
 $8,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,500
4
5
6
7
8
9
10
$8,500
11
12
13
14
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16
17
$8,500
18
19
20
21
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23
24
$8,500
25
26
27
28
29
30
31
$8,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,500
8
9
10
11
12
13
14
$12,500
15
16
17
18
19
20
21
$12,500
22
23
24
25
26
27
28
$10,500
29
30
31
 $11,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,500
5
6
7
8
9
10
11
$8,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
 $7,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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TRASJ~

Inquire
Property Details
Victorian East Chop Cottage all Newly updated, 4 Bedrooms, 3.5 Baths, Main House and Detached Guest Suite

Nestled in the highly sought-after East Chop neighborhood of Oak Bluffs, this charming Victorian cottage offers the perfect blend of classic Vineyard character and modern comfort. Ideally located within walking...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,000 - $12,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $11,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,500
4
5
6
7
8
9
10
$11,500
11
12
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16
17
$12,500
18
19
20
21
22
23
24
$12,500
25
26
27
28
29
30
31
$12,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$17,000
8
9
10
11
12
13
14
$17,000
15
16
17
18
19
20
21
$17,000
22
23
24
25
26
27
28
$12,500
29
30
31
 $10,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,000
5
6
7
8
9
10
11
$7,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
 $6,000
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45

 

 

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WESTD~

Inquire
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 - $12,400
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,500
6
7
8
9
10
11
12
$8,500
13
14
15
16
17
18
19
$8,500
20
21
22
23
24
25
26
$11,000
27
28
29
30
 $12,400
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$12,400
4
5
6
7
8
9
10
$12,400
11
12
13
14
15
16
17
$12,400
18
19
20
21
22
23
24
$12,400
25
26
27
28
29
30
31
$12,400
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,800
8
9
10
11
12
13
14
$12,800
15
16
17
18
19
20
21
$12,800
22
23
24
25
26
27
28
$11,800
29
30
31
 $9,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,000
5
6
7
8
9
10
11
$9,000
12
13
14
15
16
17
18
$9,000
19
20
21
22
23
24
25
$9,000
26
27
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 

Pool is 18 x 38 with a deep end, no diving board

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BAYLM

Inquire
Property Details
Spectacular Waterfront Views in exclusive Makonikey area, Ocean Views and Breathtaking Sunsets, Private Beach, Private Location

This serene waterfront retreat offers sweeping water views in an exceptionally private setting, yet is just a 10-minute drive from town, with access to fine dining, shopping, galleries, and entertainment....Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$12,000 - $12,000
June 2027
SuMoTuWeThFrSa
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2
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July 2027
SuMoTuWeThFrSa
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31
August 2027
SuMoTuWeThFrSaWeek
1
2
3
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7
$12,000
8
9
10
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14
$12,000
15
16
17
18
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20
21
$12,000
22
23
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25
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29
30
31
 
September 2027
SuMoTuWeThFrSa
 1
2
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26
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28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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WESTW~

Inquire
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:
$5,300 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $8,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,000
4
5
6
7
8
9
10
$8,500
11
12
13
14
15
16
17
$9,000
18
19
20
21
22
23
24
$10,000
25
26
27
28
29
30
31
$10,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,000
8
9
10
11
12
13
14
$14,000
15
16
17
18
19
20
21
$14,000
22
23
24
25
26
27
28
$12,000
29
30
31
 $8,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
6
7
8
9
10
11
$6,300
12
13
14
15
16
17
18
$5,300
19
20
21
22
23
24
25
$5,300
26
27
28
29
30
 $5,300
Clean Fee: 
$650 per week
Tax: State & Local: 
14.45
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PETEO~

Inquire
Property Details
Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully Landscaped

Outstanding vacation home, centrally located to all three down-island town centers and multiple public beaches. This lovely home in a serene setting overlooks the picturesque Little Duarte Pond in the Iron Hill...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
5
Price Range:
$7,500 - $12,000
June 2027
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
$5,000
27
28
29
30
 $6,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,000
4
5
6
7
8
9
10
$7,500
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
$8,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,000
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
$9,900
29
30
31
 
September 2027
SuMoTuWeThFrSa
 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
 
Clean Fee: 
$575 per week
Tax: State & Local: 
14.45
Add Favorite
 
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DELOR

Inquire
Property Details
Outstanding In-town Home, Gorgeous Professionally Landscaped Yard, 5 Min walk to Main Street Shops & Restaurants

Located on a quiet street in the Edgartown Village area, this lovely 5 bedroom, 3 bath Home has been all newly updated. The home is bordered by lush lawn, privacy fencing...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
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
$9,000
27
28
29
30
 $10,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$10,000
4
5
6
7
8
9
10
$12,500
11
12
13
14
15
16
17
$12,000
18
19
20
21
22
23
24
$12,000
25
26
27
28
29
30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,000
8
9
10
11
12
13
14
$16,000
15
16
17
18
19
20
21
$16,000
22
23
24
25
26
27
28
$12,000
29
30
31
 $11,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
5
6
7
8
9
10
11
$8,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
 $7,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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SAGID~

Inquire
Property Details
Newly refurbished Tri Level, Gorgeous Water Views of North Shore in Exclusive Makonikey Area

Stunning Hilltop Post & Beam Vacation Home with a relaxed coastal ambiance and picturesque distant water vistas! Nestled off Lambert’s Cove Rd in Vineyard Haven, this exquisite property resides within...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,800
6
7
8
9
10
11
12
$5,800
13
14
15
16
17
18
19
20
21
22
23
24
25
26
$6,800
27
28
29
30
 $11,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,000
4
5
6
7
8
9
10
$11,000
11
12
13
14
15
16
17
$11,000
18
19
20
21
22
23
24
$12,000
25
26
27
28
29
30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,000
8
9
10
11
12
13
14
$12,000
15
16
17
18
19
20
21
$12,000
22
23
24
25
26
27
28
$10,000
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
7
8
9
10
11
$6,500
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$6,500
26
27
28
29
30
 $5,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

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JOSEJ~

Inquire
Property Details
Exquisite Coastal Style Home, Pool, Patio, Landscaped Yard! 10 minute walk to Oak Bluffs Center, Luxury Interior, 3 bedrooms, 4 baths, Multiple Living Spaces

This newly constructed, luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with varying depths of 3 to 8 feet, a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
 $12,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$12,000
4
5
6
7
8
9
10
$12,000
11
12
13
14
15
16
17
$12,000
18
19
20
21
22
23
24
$12,000
25
26
27
28
29
30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$14,500
8
9
10
11
12
13
14
$14,500
15
16
17
18
19
20
21
$14,500
22
23
24
25
26
27
28
$12,500
29
30
31
 $11,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,500
5
6
7
8
9
10
11
$7,500
12
13
14
15
16
17
18
$6,000
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
 $6,000
Clean Fee: 
$750 per week
Tax: State & Local: 
14.45

Pool Heated to  81 degrees included in rental rate last Sat in June to first Sat in September. Pool Depth 3 feet to 8 Feet 

Pool Heated to 81 degrees June and September weeks additional $275 per week  

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