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Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

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

Note: Owner maintains security camera on front of house

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BELAT

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Property Details
Charming West Tisbury Country Setting, Access to Association Pool, and Tennis, Mulitple Indoor/Outdoor Living Spaces, Gorgeous Private Yard

Spacious, light-filled home set in a lovely community with AC and a well-equipped kitchen. The sun room opens to the deck which overlooks a lovely, private yard.  A combined living and dining...Read more

Location: 
West Tisbury
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,600 - $3,400
June 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
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13
14
15
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29
30
 
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
$3,300
19
20
21
22
23
24
25
$3,300
26
27
28
29
30
31
 $3,400
August 2026
SuMoTuWeThFrSaWeek
 1
$3,400
2
3
4
5
6
7
8
$3,400
9
10
11
12
13
14
15
$3,400
16
17
18
19
20
21
22
$3,400
23
24
25
26
27
28
29
$3,400
30
31
 $2,600
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,600
6
7
8
9
10
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12
$2,600
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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BELJA

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Property Details
Captain Swain House, Elegant Main & Guest House, 5 Bedrooms, 4.5 Baths, Multiple Indoor/Outdoor Living Spaces, 5 Minute Walk to Town, Expansive Landscaped Yard

In-Town Vacation Retreat in the William Street Historic District
Just a five-minute walk to the heart of town, this spacious and beautifully updated home blends modern comfort with timeless...Read more

Location: 
Vineyard Haven
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$4,900 - $10,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,500
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
 $8,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$8,500
19
20
21
22
23
24
25
$8,500
26
27
28
29
30
31
 $8,500
August 2026
SuMoTuWeThFrSaWeek
 1
$8,500
2
3
4
5
6
7
8
$10,000
9
10
11
12
13
14
15
$10,000
16
17
18
19
20
21
22
$10,000
23
24
25
26
27
28
29
$10,000
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
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
 $6,000
Clean Fee: 
$875 per week
Tax: State & Local: 
11.7

Owner will rent off weekend dates, for arrival and departures. Inquire for details. 

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BELLJ

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Property Details
Gorgeous Beach Retreat, 20 x 40 Heated Pebble Tec Pool, Tennis Courts, Walk or Bike to South Beach

Ferry Tickets available 7/13-7/20  & 7/20 to 7/27.  Inquire for details! (mv)

This stunning newly updated contemporary beach home is just steps from South Beach, and even fewer steps to the bike...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
4
Baths: 
3
Price Range:
$10,000 - $25,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$15,000
7
8
9
10
11
12
13
$15,000
14
15
16
17
18
19
20
$20,000
21
22
23
24
25
26
27
$25,000
28
29
30
 $25,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$25,000
5
6
7
8
9
10
11
$25,000
12
13
14
15
16
17
18
$28,500
19
20
21
22
23
24
25
$28,500
26
27
28
29
30
31
 $30,000
August 2026
SuMoTuWeThFrSaWeek
 1
$30,000
2
3
4
5
6
7
8
$30,000
9
10
11
12
13
14
15
$30,000
16
17
18
19
20
21
22
$30,000
23
24
25
26
27
28
29
$25,000
30
31
 $20,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$20,000
6
7
8
9
10
11
12
$15,000
13
14
15
16
17
18
19
$15,000
20
21
22
23
24
25
26
$15,000
27
28
29
30
 $11,000
Clean Fee: 
$725 per week
Tax: State & Local: 
11.7

Pool Heated to 82 included in rental rate July & August weeks.

Pool heated to 82 additional $300 per week June & September, May & October pool heated to 82 additional $400 per week

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BERNC

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Property Details
Mini Retreat with Pool, Private Peaceful Chilmark Location, Lucy Vincent and Menemsha Beaches Nearby.

Impeccably maintained and updated, this adorable summer home is perfect for families looking for luxury features such as quality linens in a quiet location. The 12 by 18-foot spa pool is...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,800 - $13,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,350
7
8
9
10
11
12
13
$7,350
14
15
16
17
18
19
20
$8,000
21
22
23
24
25
26
27
$12,400
28
29
30
 $13,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$13,000
5
6
7
8
9
10
11
$13,000
12
13
14
15
16
17
18
$13,000
19
20
21
22
23
24
25
$13,000
26
27
28
29
30
31
 $13,500
August 2026
SuMoTuWeThFrSaWeek
 1
$13,500
2
3
4
5
6
7
8
$13,500
9
10
11
12
13
14
15
$13,500
16
17
18
19
20
21
22
$13,500
23
24
25
26
27
28
29
$13,000
30
31
 $8,300
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,300
6
7
8
9
10
11
12
$7,650
13
14
15
16
17
18
19
$7,650
20
21
22
23
24
25
26
$7,650
27
28
29
30
 $4,800
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

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

Pool heated to 82 degrees, May, June Sept and October additional $150 per week propane surcharge

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BERNS

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Property Details
Country Charm, Screened Porch, Large Yard, Bike Paths

Large families enjoy this wonderful summer home.  Conveniently located close to West Tisbury town center.  Great summer spaces for relaxing and enjoying barbeques, lawn games, lunch on the screened porch,...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$3,600 - $5,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,600
7
8
9
10
11
12
13
$3,600
14
15
16
17
18
19
20
$3,600
21
22
23
24
25
26
27
$3,800
28
29
30
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
7
8
9
10
11
$4,800
12
13
14
15
16
17
18
$4,800
19
20
21
22
23
24
25
$4,800
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
 $3,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,900
6
7
8
9
10
11
12
$3,900
13
14
15
16
17
18
19
$3,900
20
21
22
23
24
25
26
$3,900
27
28
29
30
 $3,900
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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BETTD

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Property Details
Outstanding Luxury Family Retreat, Heated Pool, 10 Minute Walk/5 minute Bike Ride to Village Center,

This outstanding custom-built summer vacation home features an 18 X 40 ft heated pool with a bluestone patio surround.  Set on a large private yard, this designer home is just a 10-minute...Read more

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

Pool Heated to 81 July & August included in rental rate. Off season pool heat may be extra fee, please inquire! 

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BETTE

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Property Details
Luxury Gambrel Home. Heated Pool, Bluestone Patio Surround, Patio Dining, Walk to Town, 4 Bedrooms, 3.5 Baths

Unwind with family and friends in this newly constructed vacation home, featuring a heated pool and ideally situated on a peaceful lane, just a short stroll to the village center....Read more

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

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Property Details
Chilmark, Charming Updated Menemsha Home. Water Views & Sunset Views, Quintessential Beach House.

On a hilltop overlooking the ocean in Menemsha sits this authentic Vineyard home. From one of the most desirable locations on the island, it's an easy walk to the...Read more

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

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Property Details
East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

Beautiful summer home with distant water views, located in the desirable East Chop neighborhood.  This 4 bedroom, 3 bath home is located just 1.5 miles from Oak Bluffs Center & Beach. 

The...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $7,150
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
 $7,150
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,150
5
6
7
8
9
10
11
$7,150
12
13
14
15
16
17
18
$7,150
19
20
21
22
23
24
25
$7,150
26
27
28
29
30
31
 $7,150
August 2026
SuMoTuWeThFrSaWeek
 1
$7,150
2
3
4
5
6
7
8
$7,150
9
10
11
12
13
14
15
$7,150
16
17
18
19
20
21
22
$7,150
23
24
25
26
27
28
29
$7,150
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

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