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Exquisite New Contemporary Waterfront Home, Multiple Indoor& Outdoor Living Spaces with Waterviews.

This stunning luxury waterfront home, nestled on the Lagoon, offers breathtaking water views from every corner of the newly built residence. Enjoy the seamless transition between indoor and outdoor living...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
4
Price Range:
$12,500 - $16,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$12,500
7
8
9
10
11
12
13
$14,000
14
15
16
17
18
19
20
$14,000
21
22
23
24
25
26
27
$16,000
28
29
30
 $18,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$18,000
5
6
7
8
9
10
11
$18,000
12
13
14
15
16
17
18
$18,000
19
20
21
22
23
24
25
$18,000
26
27
28
29
30
31
 $18,000
August 2026
SuMoTuWeThFrSaWeek
 1
$18,000
2
3
4
5
6
7
8
$20,000
9
10
11
12
13
14
15
$20,000
16
17
18
19
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21
22
$20,000
23
24
25
26
27
28
29
$18,000
30
31
 $18,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$18,000
6
7
8
9
10
11
12
$16,000
13
14
15
16
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18
19
$14,000
20
21
22
23
24
25
26
$14,000
27
28
29
30
 $12,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner requires two week minimum booking during months July & August

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THOM3

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Property Details
Luxury 2-Bedroom Condo at Mariner’s Landing – Unit #3 of 8

Discover the perfect retreat just a short stroll from Edgartown Village Center. This condo offers easy access to scenic bike paths that lead to both the village center and the beautiful...Read more

Location: 
Edgartown
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$3,000 - $4,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
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
$3,100
28
29
30
 $4,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,200
5
6
7
8
9
10
11
$4,200
12
13
14
15
16
17
18
$4,200
19
20
21
22
23
24
25
$4,500
26
27
28
29
30
31
 $4,500
August 2026
SuMoTuWeThFrSaWeek
 1
$4,500
2
3
4
5
6
7
8
$5,000
9
10
11
12
13
14
15
$5,000
16
17
18
19
20
21
22
$5,000
23
24
25
26
27
28
29
$4,200
30
31
 $4,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,200
6
7
8
9
10
11
12
$3,100
13
14
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16
17
18
19
$3,100
20
21
22
23
24
25
26
$3,000
27
28
29
30
 $3,000
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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THOMR

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Property Details
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:
$17,850 - $17,850
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$12,400
7
8
9
10
11
12
13
$13,600
14
15
16
17
18
19
20
$14,500
21
22
23
24
25
26
27
$16,650
28
29
30
 $16,650
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$16,650
5
6
7
8
9
10
11
$17,250
12
13
14
15
16
17
18
$17,250
19
20
21
22
23
24
25
$17,250
26
27
28
29
30
31
 $17,850
August 2026
SuMoTuWeThFrSaWeek
 1
$17,850
2
3
4
5
6
7
8
9
10
11
12
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14
15
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17
18
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20
21
22
$15,130
23
24
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27
28
29
$13,900
30
31
 $12,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,700
6
7
8
9
10
11
12
$11,650
13
14
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18
19
$10,300
20
21
22
23
24
25
26
$9,100
27
28
29
30
 $8,150
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:
$3,100 - $6,900
June 2026
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
 $6,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,400
5
6
7
8
9
10
11
$6,400
12
13
14
15
16
17
18
$6,400
19
20
21
22
23
24
25
$6,400
26
27
28
29
30
31
 $6,900
August 2026
SuMoTuWeThFrSaWeek
 1
$6,900
2
3
4
5
6
7
8
$6,800
9
10
11
12
13
14
15
$6,800
16
17
18
19
20
21
22
$6,800
23
24
25
26
27
28
29
$6,800
30
31
 $6,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,900
6
7
8
9
10
11
12
$3,800
13
14
15
16
17
18
19
$3,800
20
21
22
23
24
25
26
$3,800
27
28
29
30
 $3,800
Clean Fee: 
$500 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: 
4
Baths: 
4
Price Range:
$3,800 - $6,300
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,800
7
8
9
10
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12
13
$4,500
14
15
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17
18
19
20
$4,500
21
22
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24
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27
28
29
30
 
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
$6,300
12
13
14
15
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17
18
$6,300
19
20
21
22
23
24
25
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSa
 1
2
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September 2026
SuMoTuWeThFrSa
 1
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20
21
22
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24
25
26
27
28
29
30
 
Clean Fee: 
$575 per week
Tax: State & Local: 
11.7
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TOTHG

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Property Details

Note: Older style TVs seen in photos have been replaced. 

This bright and classic summer cottage is ideally located just one mile from Oak Bluffs town center and all the...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$4,000 - $4,950
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
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13
$4,000
14
15
16
17
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20
$4,000
21
22
23
24
25
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27
$4,000
28
29
30
 
July 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
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27
28
29
30
31
 $4,950
August 2026
SuMoTuWeThFrSaWeek
 1
$4,950
2
3
4
5
6
7
8
$4,950
9
10
11
12
13
14
15
$4,950
16
17
18
19
20
21
22
$4,950
23
24
25
26
27
28
29
$4,950
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
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:
$0 - $0
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
 $5,350
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,350
5
6
7
8
9
10
11
$5,350
12
13
14
15
16
17
18
$5,350
19
20
21
22
23
24
25
$5,350
26
27
28
29
30
31
 $7,000
August 2026
SuMoTuWeThFrSaWeek
 1
$7,000
2
3
4
5
6
7
8
$7,000
9
10
11
12
13
14
15
$7,200
16
17
18
19
20
21
22
$7,500
23
24
25
26
27
28
29
30
31
 
September 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
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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: 
$500 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

Nestled amidst picturesque grounds and gardens, this enchanting vacation getaway boasts an array of indoor and outdoor spaces seamlessly interconnected. The focal points of summer relaxation include a 14 x...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$8,000 - $8,000
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
$12,000
28
29
30
 $15,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$15,000
5
6
7
8
9
10
11
$15,000
12
13
14
15
16
17
18
$15,000
19
20
21
22
23
24
25
$15,000
26
27
28
29
30
31
 $15,000
August 2026
SuMoTuWeThFrSaWeek
 1
$15,000
2
3
4
5
6
7
8
$15,000
9
10
11
12
13
14
15
$15,000
16
17
18
19
20
21
22
$15,000
23
24
25
26
27
28
29
$11,000
30
31
 $8,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
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

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:
$0 - $0
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
 $15,600
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$15,600
5
6
7
8
9
10
11
$15,600
12
13
14
15
16
17
18
$15,600
19
20
21
22
23
24
25
$15,600
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSa
 1
2
3
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5
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September 2026
SuMoTuWeThFrSa
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21
22
23
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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:
$0 - $0
June 2026
SuMoTuWeThFrSa
 1
2
3
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5
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July 2026
SuMoTuWeThFrSa
 1
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28
29
30
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$8,500
9
10
11
12
13
14
15
$8,500
16
17
18
19
20
21
22
$8,500
23
24
25
26
27
28
29
$6,500
30
31
 
September 2026
SuMoTuWeThFrSa
 1
2
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12
13
14
15
16
17
18
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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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