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Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi

Centrally located in the Hidden Cove community of homes on the outskirts of Oak Bluffs. Lovely area to bike, walk, or play tennis at the association courts. 

The main level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,400 - $4,300
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,400
6
7
8
9
10
11
12
$3,050
13
14
15
16
17
18
19
$3,050
20
21
22
23
24
25
26
$3,200
27
28
29
30
 $4,100
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,100
4
5
6
7
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9
10
$4,100
11
12
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17
$4,300
18
19
20
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24
$4,300
25
26
27
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29
30
31
$4,600
August 2027
SuMoTuWeThFrSaWeek
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2
3
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5
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7
$4,720
8
9
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11
12
13
14
$4,720
15
16
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18
19
20
21
$4,720
22
23
24
25
26
27
28
$3,570
29
30
31
 $4,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,100
5
6
7
8
9
10
11
$4,100
12
13
14
15
16
17
18
$4,100
19
20
21
22
23
24
25
$4,100
26
27
28
29
30
 $4,100
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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Meadow House, 5 Minute Drive to Lambert's Cove Beach, Sleeps 6, AC, Private, Quiet Location yet close to Town and Beach, AC

Immaculately clean cabinesque home, privately located off of Lambert's Cove Rd, yet just a 5-minute drive to beautiful Lambert's Cove Beach and 10 minutes from Vineyard Haven town center. 

This three-bedroom home...Read more

Location: 
West Tisbury
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,100 - $3,700
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,300
6
7
8
9
10
11
12
$2,300
13
14
15
16
17
18
19
$2,300
20
21
22
23
24
25
26
$2,950
27
28
29
30
 $3,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,250
4
5
6
7
8
9
10
$3,250
11
12
13
14
15
16
17
$3,250
18
19
20
21
22
23
24
$3,500
25
26
27
28
29
30
31
$3,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,700
8
9
10
11
12
13
14
$3,700
15
16
17
18
19
20
21
$3,700
22
23
24
25
26
27
28
$3,200
29
30
31
 $2,300
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$2,300
5
6
7
8
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$2,300
12
13
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18
$2,300
19
20
21
22
23
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25
$2,300
26
27
28
29
30
 $2,300
Clean Fee: 
$405 per week
Tax: State & Local: 
11.7
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Mink Meadow Guest Cottage, Overlooks Golf Course, Walk to Beach 5 min walk from House, Mink Meadows Golf Course, 1 mile to Clubhouse

Cozy guest cottage with designer touches throughout. As the guest cottage to the main house, this adorable cottage is private from the main house and has its own drive and...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,900 - $1,900
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$1,900
6
7
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10
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12
$1,900
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 $2,100
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$2,100
4
5
6
7
8
9
10
$2,100
11
12
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$2,100
18
19
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23
24
$2,100
25
26
27
28
29
30
31
$2,100
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,100
8
9
10
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14
$2,100
15
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21
$2,100
22
23
24
25
26
27
28
$2,100
29
30
31
 $1,900
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$1,900
5
6
7
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$1,900
12
13
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18
$1,900
19
20
21
22
23
24
25
$1,900
26
27
28
29
30
 $1,900
Clean Fee: 
$150 per week
Tax: State & Local: 
11.7
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Mink Meadows Family Compound, Private Heated Pool, Walk or Drive to Private Association Beach, Beautifully Landscaped Yard, Deck and Patio, Golf 1 Mile from House

Spacious 4 Bedroom, 3.5 bath family compound with 28 x 14  heated pool, multiple indoor/outdoor living spaces situated in Mink Meadows Association. 

Mink Meadows Public Golf Course is just a short drive...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $6,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,400
6
7
8
9
10
11
12
$4,400
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
 $7,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,800
4
5
6
7
8
9
10
$7,800
11
12
13
14
15
16
17
$7,800
18
19
20
21
22
23
24
$7,800
25
26
27
28
29
30
31
$8,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,500
8
9
10
11
12
13
14
$8,500
15
16
17
18
19
20
21
$8,500
22
23
24
25
26
27
28
$8,500
29
30
31
 $6,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,500
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
 $6,500
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

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

 

Pool heated to 81 degrees June & September additional $250 per week. Requests for higher temperature, please contact your agent for details. 

 

Pool heated to 81 degrees May & October additional $350 per week. Requests for higher temperature, please contact your agent for details.

 

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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 - $3,500
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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30
31
August 2027
SuMoTuWeThFrSa
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September 2027
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: 
$400 per week
Tax: State & Local: 
11.7
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Quintessential West Chop Waterfront Home. Private Beach, Spectacular Views

Enjoy the essence of summer at this waterfront home with a private beach just 50 yards in front of the house. Evenings enjoy the magnificent sunsets while relaxing on the...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$0 - $0
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
$25,000
27
28
29
30
 $28,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$28,000
4
5
6
7
8
9
10
$25,000
11
12
13
14
15
16
17
$25,000
18
19
20
21
22
23
24
$25,000
25
26
27
28
29
30
31
$28,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$28,000
8
9
10
11
12
13
14
$28,000
15
16
17
18
19
20
21
$28,000
22
23
24
25
26
27
28
$28,000
29
30
31
 $25,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$25,000
5
6
7
8
9
10
11
$17,500
12
13
14
15
16
17
18
$17,500
19
20
21
22
23
24
25
$17,500
26
27
28
29
30
 $17,500
Clean Fee: 
$800 per week
Tax: State & Local: 
11.7
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Lovely updated Home , Village Area Edgartown, 7 minute Walk to Main St. Bike Paths at end of Street.

Minutes from downtown Edgartown's shops & restaurants, this cape style home features open concept living, air conditioning, a mini-split in the main living area, window units in all but 1st level...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,650 - $6,650
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSa
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September 2027
SuMoTuWeThFrSa
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22
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25
26
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29
30
 
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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Exquisite Estate Vacation Retreat, Main & Guest House, Affinity Pool, South Shore Waterviews, Sleeps 12 in 6 Bedrooms, Multiple Living & Entertaining Areas both indoors & out

Outstanding Chilmark Estate tucked on 9.5 private acres with sweeping views of the Atlantic Ocean and Chilmark Pond. This unique contemporary home features a heated infinity pool, screened porch, and expansive deck with...Read more

Location: 
Chilmark
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$30,000 - $55,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$35,000
6
7
8
9
10
11
12
$35,000
13
14
15
16
17
18
19
$35,000
20
21
22
23
24
25
26
$40,000
27
28
29
30
 $55,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$55,000
4
5
6
7
8
9
10
$50,000
11
12
13
14
15
16
17
$50,000
18
19
20
21
22
23
24
$50,000
25
26
27
28
29
30
31
$50,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$50,000
8
9
10
11
12
13
14
$50,000
15
16
17
18
19
20
21
$50,000
22
23
24
25
26
27
28
$50,000
29
30
31
 $30,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$30,000
5
6
7
8
9
10
11
$30,000
12
13
14
15
16
17
18
$30,000
19
20
21
22
23
24
25
$30,000
26
27
28
29
30
 $30,000
Clean Fee: 
$2000 per week
Tax: State & Local: 
11.7

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

Pool heated to 82 degrees June & September additional surcharge $350 per week

Pool heated to 82 degrees May & October additional surcharge $450 per week

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Beautiful Oak Bluffs Home, 20 x 40 Heated Pool, 6 Bedrooms, 4 baths, Sleeps 14, Screened Porch, Multiple Living Spaces

Oak Bluffs vacation retreat with multiple indoor, and outdoor living and entertaining areas. The highlight of this spacious summer home is the heated Gunite pool with waterfall, bluestone patio, and...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
6
Baths: 
4
Price Range:
$16,900 - $16,900
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$16,900
6
7
8
9
10
11
12
$16,900
13
14
15
16
17
18
19
$16,900
20
21
22
23
24
25
26
$16,900
27
28
29
30
 $18,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$18,500
4
5
6
7
8
9
10
$19,400
11
12
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17
$19,500
18
19
20
21
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23
24
$20,500
25
26
27
28
29
30
31
$20,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$20,500
8
9
10
11
12
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14
$20,500
15
16
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18
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20
21
$20,500
22
23
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25
26
27
28
$20,000
29
30
31
 $16,900
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$16,900
5
6
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$16,900
12
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$16,900
19
20
21
22
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25
$16,900
26
27
28
29
30
 $16,900
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool Heated to 82 included in rental rate July and August, Spa in pool is heated to same the temperature as pool.

 

Spa Heat $250 per week. Available upon request. 

 

Pool Heated to 82 June & Sept additional $275 per week. May & October additional $350 per week. 

 

Firepit seen in photos is not for renter use. 

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Menemsha, Water View, Walk to beach
Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,950 - $3,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$1,950
6
7
8
9
10
11
12
$1,950
13
14
15
16
17
18
19
$1,950
20
21
22
23
24
25
26
$1,950
27
28
29
30
 $3,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,000
4
5
6
7
8
9
10
$3,000
11
12
13
14
15
16
17
$3,000
18
19
20
21
22
23
24
$3,000
25
26
27
28
29
30
31
$3,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,200
8
9
10
11
12
13
14
$3,200
15
16
17
18
19
20
21
$3,200
22
23
24
25
26
27
28
$3,200
29
30
31
 $3,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,200
5
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12
13
14
15
16
17
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21
22
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27
28
29
30
 
Clean Fee: 
$200 per week
Tax: State & Local: 
11.7

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