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Lovely Cape Home, Newly Updated, Private Back Deck with Outdoor Dining & Grill, 3 Bedrooms w/AC and TV, 1.5 baths

Nestled on a serene lane in the outskirts of Vineyard Haven, this newly updated & charming Cape Style residence exudes chic charm. Step inside to discover an inviting open layout...Read more

Location: 
Vineyard Haven
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $3,700
June 2025
SuMoTuWeThFrSaWeek
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 $3,700
July 2025
SuMoTuWeThFrSaWeek
 1
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$3,700
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$3,700
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$3,700
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$3,700
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
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$4,000
10
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$4,400
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$4,400
24
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29
30
$4,000
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$3,500
7
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$3,000
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$3,000
21
22
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27
$3,000
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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THOHP

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Property Details
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:
$10,000 - $18,000
June 2025
SuMoTuWeThFrSaWeek
1
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 $16,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
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$16,000
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$18,000
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$18,000
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21
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$18,000
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28
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30
31
 $18,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$18,000
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$20,000
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$20,000
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$20,000
24
25
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27
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29
30
$18,000
31
 $18,000
September 2025
SuMoTuWeThFrSaWeek
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$18,000
7
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$16,000
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$14,000
21
22
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27
$14,000
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 - $5,000
June 2025
SuMoTuWeThFrSaWeek
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29
30
 $4,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,200
6
7
8
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10
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12
$3,800
13
14
15
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18
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$3,800
20
21
22
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25
26
$4,500
27
28
29
30
31
 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,500
3
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$5,000
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$5,000
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$5,000
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30
$4,200
31
 $4,200
September 2025
SuMoTuWeThFrSaWeek
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3
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$4,200
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$3,100
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$3,100
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$3,000
28
29
30
 $3,000
Clean Fee: 
$300 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:
$7,430 - $12,650
June 2025
SuMoTuWeThFrSaWeek
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 $15,130
July 2025
SuMoTuWeThFrSaWeek
 1
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3
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$15,130
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12
$15,680
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19
$15,680
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26
$15,680
27
28
29
30
31
 $16,220
August 2025
SuMoTuWeThFrSaWeek
 1
2
$16,220
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$16,220
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$16,220
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$13,750
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$12,650
31
 $11,550
September 2025
SuMoTuWeThFrSaWeek
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$11,550
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$10,580
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$9,350
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22
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$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:
$3,100 - $6,300
June 2025
SuMoTuWeThFrSaWeek
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 $6,300
July 2025
SuMoTuWeThFrSaWeek
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$6,300
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$6,300
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$6,300
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$6,300
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31
 $6,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,800
3
4
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6
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$6,800
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$6,800
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$6,800
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30
$6,800
31
 $5,820
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,820
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$3,800
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$3,800
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22
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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:
$2,700 - $3,800
June 2025
SuMoTuWeThFrSaWeek
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 $6,100
July 2025
SuMoTuWeThFrSaWeek
 1
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$6,100
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$6,100
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$6,100
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21
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$6,300
27
28
29
30
31
 $6,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,600
3
4
5
6
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$6,600
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11
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$6,600
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18
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21
22
23
$6,600
24
25
26
27
28
29
30
$5,900
31
 $3,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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6
$3,800
7
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$3,800
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$3,800
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22
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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:
$3,900 - $4,950
June 2025
SuMoTuWeThFrSaWeek
1
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 $4,950
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$4,950
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$4,950
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$4,950
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21
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$4,950
27
28
29
30
31
 $4,950
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,950
3
4
5
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$4,950
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$4,950
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18
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$4,950
24
25
26
27
28
29
30
$4,950
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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$4,000
7
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$3,900
14
15
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$3,900
21
22
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24
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27
$3,900
28
29
30
 
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 2025
SuMoTuWeThFrSaWeek
1
2
3
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5
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13
14
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30
 $5,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,200
6
7
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12
$5,200
13
14
15
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19
$5,200
20
21
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25
26
$5,200
27
28
29
30
31
 $6,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,800
3
4
5
6
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9
$7,000
10
11
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13
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$7,250
17
18
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20
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24
25
26
27
28
29
30
31
 
September 2025
SuMoTuWeThFrSa
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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:
$12,000 - $14,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
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10
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13
14
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17
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 $12,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,000
6
7
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$13,000
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14
15
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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
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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 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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