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High St House, Ideal In-town Location, Beautiful 4 Bedroom, 4 .5 Bath Home, Walk to Edgartown Village Center, 5 Minute Drive to South Beach

Beautiful village area colonial with contemporary designer interior and luxury amenities. For those who love an in-town location with easy walking distance to Main St, this home provides the perfect location. South...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$10 - $13,200
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,280
8
9
10
11
12
13
14
$12,370
15
16
17
18
19
20
21
$13,200
22
23
24
25
26
27
28
$15,130
29
30
 $15,130
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$15,130
6
7
8
9
10
11
12
$15,680
13
14
15
16
17
18
19
$15,680
20
21
22
23
24
25
26
$15,680
27
28
29
30
31
 $16,220
August 2025
SuMoTuWeThFrSaWeek
 1
2
$16,220
3
4
5
6
7
8
9
$16,220
10
11
12
13
14
15
16
$16,220
17
18
19
20
21
22
23
$13,750
24
25
26
27
28
29
30
$12,650
31
 $11,550
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$11,550
7
8
9
10
11
12
13
$10,580
14
15
16
17
18
19
20
$9,350
21
22
23
24
25
26
27
$8,250
28
29
30
 $7,430
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7
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THOMS

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Property Details
New Modern Farmhouse Design, Great Location!, Wraparound Farmers Porch, Deck Area.

Beautiful new 4 bedroom home, 3.5 bath sleeps 8.  Ideally located just 2 miles from the center of Oak Bluffs and just minutes by car to the towns of Vineyard Haven and...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $5,820
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,800
8
9
10
11
12
13
14
$3,800
15
16
17
18
19
20
21
$3,800
22
23
24
25
26
27
28
$5,500
29
30
 $6,300
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,300
6
7
8
9
10
11
12
$6,300
13
14
15
16
17
18
19
$6,300
20
21
22
23
24
25
26
$6,300
27
28
29
30
31
 $6,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,800
3
4
5
6
7
8
9
$6,800
10
11
12
13
14
15
16
$6,800
17
18
19
20
21
22
23
$6,800
24
25
26
27
28
29
30
$6,800
31
 $5,820
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,820
7
8
9
10
11
12
13
$3,800
14
15
16
17
18
19
20
$3,800
21
22
23
24
25
26
27
$3,800
28
29
30
 $3,800
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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THORB

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Property Details
Contemporary 5 Bedroom 4 Bath, Multiple Living Spaces, Walk to Oak Bluffs Center and Inkwell Beach-10 minutes

Extended families are sure to enjoy this tri-level home featuring an open floor plan on the main level, a large main living room, and three den/TV areas, one on the first level...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$10 - $6,100
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,800
8
9
10
11
12
13
14
$3,800
15
16
17
18
19
20
21
$3,800
22
23
24
25
26
27
28
$5,100
29
30
 $6,100
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,100
6
7
8
9
10
11
12
$6,100
13
14
15
16
17
18
19
$6,100
20
21
22
23
24
25
26
$6,300
27
28
29
30
31
 $6,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,600
3
4
5
6
7
8
9
$6,600
10
11
12
13
14
15
16
$6,600
17
18
19
20
21
22
23
$6,600
24
25
26
27
28
29
30
$5,900
31
 $3,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,800
7
8
9
10
11
12
13
$3,800
14
15
16
17
18
19
20
$3,800
21
22
23
24
25
26
27
$3,800
28
29
30
 $2,700
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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TOTHG

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Property Details
Adorable Updated Vineyard Cottage, Lovely Landscaped Yard, Central A/C, Flat Screen TV, Bike Paths at end of Drive, One Mile to Oak Bluffs Center

Bright and classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Inkwell Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Ocean...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$10 - $4,950
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,700
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$4,950
22
23
24
25
26
27
28
$4,950
29
30
 $4,950
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,950
6
7
8
9
10
11
12
$4,950
13
14
15
16
17
18
19
$4,950
20
21
22
23
24
25
26
$4,950
27
28
29
30
31
 $4,950
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,950
3
4
5
6
7
8
9
$4,950
10
11
12
13
14
15
16
$4,950
17
18
19
20
21
22
23
$4,950
24
25
26
27
28
29
30
$4,950
31
 $4,950
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,950
7
8
9
10
11
12
13
$4,950
14
15
16
17
18
19
20
$4,950
21
22
23
24
25
26
27
$4,950
28
29
30
 $4,950
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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TRAVM

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Property Details
Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.

Visitors will enjoy this delightful &  comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. 

Relax in the breeze with your morning coffee on the front...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $10
June 2025
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
 $5,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,200
6
7
8
9
10
11
12
$5,200
13
14
15
16
17
18
19
$5,200
20
21
22
23
24
25
26
$5,200
27
28
29
30
31
 $6,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,800
3
4
5
6
7
8
9
$7,000
10
11
12
13
14
15
16
$7,250
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2025
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: 
$475 per week
Tax: State & Local: 
11.7
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ULYPA

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Property Details
Edgartown Retreat-Impeccably Maintained, Heated Pool -14 x 32', Screened Porch, Bluestone Patio, Exqusite Grounds and Gardens, Multiple Interior and Exterior Living Spaces

NOTE:  New for 2025: The owner is having a custom built 1 bedroom guest house added to the property that will sleep 2, featuring a living, dining, kitchen area, a bedroom,...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $10
June 2025
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
 $12,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,000
6
7
8
9
10
11
12
$13,000
13
14
15
16
17
18
19
$13,000
20
21
22
23
24
25
26
$13,000
27
28
29
30
31
 $14,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$14,000
3
4
5
6
7
8
9
$14,000
10
11
12
13
14
15
16
$14,000
17
18
19
20
21
22
23
$14,000
24
25
26
27
28
29
30
$12,000
31
 
September 2025
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: 
$400 per week
Tax: State & Local: 
11.7

Ferry Tickets available for week 8/1-8/8 - please inquire

 

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

Pool Heat shoulder season weeks additional propane surcharge, please inquire! 

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URMST

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Property Details
West Chop, Waterfront, Private Beach

Summer Compound in a majestic location.  Vintage vacation home perfect for large family gatherings.  Enjoy sweeping ocean views from the large comfortably furnished veranda.  A large screened porch offers seating...Read more

Location: 
Vineyard Haven
Sleeps: 
14
Bedrooms: 
6
Baths: 
2
Price Range:
$10 - $10
June 2025
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
 $15,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$15,600
6
7
8
9
10
11
12
$15,600
13
14
15
16
17
18
19
$15,600
20
21
22
23
24
25
26
$15,600
27
28
29
30
31
 $15,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$15,600
3
4
5
6
7
8
9
$15,600
10
11
12
13
14
15
16
$15,600
17
18
19
20
21
22
23
$15,600
24
25
26
27
28
29
30
$15,600
31
 
September 2025
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: 
$875 per rental period
Tax: State & Local: 
11.7
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VANA2

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Property Details
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $6,500
June 2025
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
 $8,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
31
 $7,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,000
3
4
5
6
7
8
9
$7,500
10
11
12
13
14
15
16
$7,500
17
18
19
20
21
22
23
$8,500
24
25
26
27
28
29
30
$6,500
31
 
September 2025
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: 
$450 per week
Tax: State & Local: 
11.7
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VANAL

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Property Details
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:
$10 - $4,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$4,000
29
30
 $5,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
31
 $6,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,500
3
4
5
6
7
8
9
$6,500
10
11
12
13
14
15
16
$6,500
17
18
19
20
21
22
23
$7,500
24
25
26
27
28
29
30
$4,500
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
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
 $3,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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:
$10 - $3,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,000
29
30
 $3,500
July 2025
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
31
 $3,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,500
3
4
5
6
7
8
9
$3,500
10
11
12
13
14
15
16
$3,500
17
18
19
20
21
22
23
$3,500
24
25
26
27
28
29
30
$3,500
31
 $3,200
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,200
7
8
9
10
11
12
13
$3,200
14
15
16
17
18
19
20
$3,200
21
22
23
24
25
26
27
$3,200
28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7

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