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Makonikey, Water View, Walk to Private Association Beach, Large Yard Area.

Located in Makonikey,  a private enclave of homes on the North Shore.

Beautifully maintained four-bedroom vacation home with water views. Just a short walk or drive to private Makonikey association beach,  This...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$4,800 - $4,800
June 2027
SuMoTuWeThFrSaWeek
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 $4,800
July 2027
SuMoTuWeThFrSaWeek
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2
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$4,800
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$4,800
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$4,800
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$4,800
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$4,800
August 2027
SuMoTuWeThFrSaWeek
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$4,800
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$4,800
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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KEANM

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Property Details
Lovely Oak Bluffs Home, 3 Bedrooms, 2.5 Baths, Sleeps 7. Set just on the Outskirts of Oak Bluffs Center

Lovely 3 bedroom, 2.5 bath home that sleeps 7. This sweet home is bordered by a large yard and is located just on the outskirts of Oak Bluffs. The patio...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$2,000 - $4,800
June 2027
SuMoTuWeThFrSaWeek
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2
3
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$2,500
6
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$2,500
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$3,000
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21
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25
26
$3,000
27
28
29
30
 $4,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,800
4
5
6
7
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10
$4,800
11
12
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$4,800
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19
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$4,800
25
26
27
28
29
30
31
August 2027
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
29
30
31
 $4,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
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$4,500
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Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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HUT19

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Property Details
Tucked in Heart of West Tisbury, 4 bedrooms, 2 baths, Open Living Spaces, Private Deck
Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,620 - $4,720
June 2027
SuMoTuWeThFrSaWeek
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2
3
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$2,620
6
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$2,620
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$2,620
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$2,620
27
28
29
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 $3,150
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,150
4
5
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10
$3,990
11
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$3,990
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$3,990
25
26
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29
30
31
$3,990
August 2027
SuMoTuWeThFrSaWeek
1
2
3
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$4,720
8
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$4,720
15
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$4,720
22
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$4,720
29
30
31
 $4,720
September 2027
SuMoTuWeThFrSaWeek
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2
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$4,720
5
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$3,360
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$3,360
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21
22
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25
$3,360
26
27
28
29
30
 $3,200
Clean Fee: 
Tax: State & Local: 
11.7
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LIJOY

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Property Details
Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, Bike Paths at Entrance to Neighborhood, Multiple Beaches Near By

Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,700 - $4,700
June 2027
SuMoTuWeThFrSaWeek
 1
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12
13
14
15
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19
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21
22
23
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25
26
27
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29
30
 $6,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,800
4
5
6
7
8
9
10
$7,200
11
12
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$7,000
18
19
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$7,000
25
26
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$7,300
August 2027
SuMoTuWeThFrSaWeek
1
2
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$7,300
8
9
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$7,800
15
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$7,800
22
23
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$7,300
29
30
31
 $6,800
September 2027
SuMoTuWeThFrSaWeek
 1
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$6,800
5
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$7,000
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30
 
Clean Fee: 
$420 per week
Tax: State & Local: 
14.45
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COWAC

Inquire
Property Details
Lovely Cape, 7 minute walk to town and harbor area, 4 bedrooms, 3 baths, sleeps 7

Lovely 4 bedroom, 3 bath home, pristinely maintained and ideally located just on the outskirts of Oak Bluffs on a quiet street. Short walk to town center and Oak Bluffs town...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $4,700
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
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10
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12
$3,000
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$3,000
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$3,800
27
28
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 $4,700
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,700
4
5
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$4,700
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$4,700
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$4,700
25
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$5,350
August 2027
SuMoTuWeThFrSaWeek
1
2
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$5,400
8
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$5,600
15
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$5,400
22
23
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25
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$4,400
29
30
31
 $3,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,200
5
6
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$3,200
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13
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$3,000
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20
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$3,000
26
27
28
29
30
 $3,000
Clean Fee: 
$450 per week
Tax: State & Local: 
14.45
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KOEOB

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Property Details
Adorable Updated 2 Bedroom 1.5 Bath Cottage, Walk to Town, Harbor and Beach

If you are looking for an adorable cottage-style home in the center of Oak Bluffs this newly updated, tastefully decorated 2 bedroom, with one full bath and a half bath, is sure to...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$1,900 - $4,600
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,600
6
7
8
9
10
11
12
$2,600
13
14
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$2,800
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$2,800
27
28
29
30
 $3,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,900
4
5
6
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9
10
$3,900
11
12
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$3,900
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19
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$3,900
25
26
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30
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$3,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,600
8
9
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14
$4,600
15
16
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19
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21
22
23
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29
30
31
 $3,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
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$3,100
5
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29
30
 $2,600
Clean Fee: 
$275 per week
Tax: State & Local: 
14.45
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ST304

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Property Details
Sea View Condominium, Water View, Walk to Town & Beach-Across the Street

Sea View Condominium with a breathtaking view of Nantucket Sound from almost every room. Just steps from the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$4,500 - $4,500
June 2027
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July 2027
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August 2027
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$275 per week
Tax: State & Local: 
14.45
Add Favorite
 
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WILCM

Inquire
Property Details
Hidden Cove Retreat, Walk to Association Tennis/Pickleball Courts, 3 Bedrooms, 2.5 Baths, Screened Porch and Deck

Nestled in the charming Hidden Cove community, this adorable contemporary home resides on a tranquil street within walking distance of the association's tennis/pickleball courts. Its central location places it just a...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $4,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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10
11
12
13
14
15
16
17
18
19
20
21
22
23
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25
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29
30
 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,500
4
5
6
7
8
9
10
$4,500
11
12
13
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16
17
$4,500
18
19
20
21
22
23
24
$4,500
25
26
27
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29
30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,500
8
9
10
11
12
13
14
$6,500
15
16
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18
19
20
21
$5,000
22
23
24
25
26
27
28
$5,000
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
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12
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17
18
19
20
21
22
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25
26
27
28
29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
14.45
Add Favorite
 
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MCGOK

Inquire
Property Details
Cozy Contemporary Home in Dodger's Hole, Centrally Located to Towns and Beaches, Wrap Around Deck, WiFI

MVVR Exclusive Listing: Open concept three-bedroom, 2 bath home centrally located in Dodger's Hole area on the outskirts of Edgartown. Bike Paths 500 yards from the house connect to additional...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,700 - $4,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
 $4,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,000
4
5
6
7
8
9
10
$4,000
11
12
13
14
15
16
17
$4,000
18
19
20
21
22
23
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25
26
27
28
29
30
31
$4,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,500
8
9
10
11
12
13
14
$4,500
15
16
17
18
19
20
21
$4,500
22
23
24
25
26
27
28
$4,200
29
30
31
 $3,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,500
5
6
7
8
9
10
11
$3,500
12
13
14
15
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18
$2,700
19
20
21
22
23
24
25
$2,700
26
27
28
29
30
 $2,700
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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FISHJ

Inquire
Property Details
Stylish Contemporary Vacation Home situated in Meadow View Farms, Open Light Filled Design, Expansive Private Deck

Come and enjoy this light-filled, beautifully maintained, three-level contemporary home complete with gardens, landscaped yard, and a children’s backyard playground.  

The main level features an open kitchen, dining, and TV/living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $4,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
 $6,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,900
4
5
6
7
8
9
10
$6,900
11
12
13
14
15
16
17
$6,900
18
19
20
21
22
23
24
$6,900
25
26
27
28
29
30
31
$6,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,900
8
9
10
11
12
13
14
$6,900
15
16
17
18
19
20
21
$6,900
22
23
24
25
26
27
28
$6,900
29
30
31
 $6,900
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,900
5
6
7
8
9
10
11
$5,500
12
13
14
15
16
17
18
$5,200
19
20
21
22
23
24
25
$5,200
26
27
28
29
30
 $5,200
Clean Fee: 
$425 per week
Tax: State & Local: 
14.45
Add Favorite
 
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BEG21

Inquire
Property Details
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:
$4,500 - $4,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
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
 $6,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,500
4
5
6
7
8
9
10
$7,000
11
12
13
14
15
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17
$7,000
18
19
20
21
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23
24
$7,000
25
26
27
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29
30
31
$7,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,000
8
9
10
11
12
13
14
$8,000
15
16
17
18
19
20
21
$8,000
22
23
24
25
26
27
28
$8,000
29
30
31
 $3,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,500
5
6
7
8
9
10
11
$3,500
12
13
14
15
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17
18
$3,500
19
20
21
22
23
24
25
$3,500
26
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
14.45

Note: Owner maintains security camera on front of house

Add Favorite
 
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MACFC

Inquire
Property Details
Beautiful Newly Renovated Katama Area Home. Multiple Indoor, Outdoor Living Spaces, Sleeps 8.

Nestled within the scenic Katama area of Edgartown, this home boasts a spacious layout and exquisite renovations, complemented by professional decor. Its prime location offers easy access to both Edgartown...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,500 - $4,500
June 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

 

 

 

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SWEEC

Inquire
Property Details
Lovely Updated Cape Style Home, Beautifully Landscaped Yard, Deck & Patio with Multiple Seating Areas & Outdoor Dining

Nestled in a peaceful lane in Edgartown's desirable Dodger’s Hole Area, this charming Cape-style home offers a central location with easy access to Edgartown, Oak Bluffs, Vineyard Haven, and several...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,500 - $4,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
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$3,000
6
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$3,000
13
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$3,500
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$4,000
27
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 $4,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$4,500
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$4,500
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$4,500
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$4,500
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$4,500
August 2027
SuMoTuWeThFrSaWeek
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$6,500
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$6,500
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$6,500
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$4,500
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 $4,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
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$4,500
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$3,500
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$3,000
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$2,500
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29
30
 $2,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BROVH

Inquire
Property Details
Quintessential In-town Vineyard Haven Home, Recently Updated, Walk to all the Village has to offer. Owen Park on the Harbor just Across the Street, Private Yard and Patio, 5 Bedrooms, 4 Baths

Welcome to the Edmond Crowell House, ideally located in the Historic District of Upper Main Street in Vineyard Haven. This is the perfect vacation retreat for those who appreciate the...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$4,500 - $4,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
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$5,500
6
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$5,500
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$6,500
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$6,500
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 $7,900
July 2027
SuMoTuWeThFrSaWeek
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2
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$7,900
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$7,900
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$7,900
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$7,900
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$7,900
August 2027
SuMoTuWeThFrSaWeek
1
2
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$7,900
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$7,900
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$7,900
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$7,900
29
30
31
 $4,370
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,370
5
6
7
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$4,500
26
27
28
29
30
 $4,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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SAVAJ

Inquire
Property Details
Tashmoo Cove Townhouse, Association Pool, Association Tennis Courts.

MVVR Exclusive: Beautifully appointed with a mix of Asian and Tibetan antique furniture, furnishings from Napa Valley, Sundance, and Pottery Barn, and original artwork, this highly desirable townhouse provides a luxurious...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$2,200 - $4,400
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$3,270
6
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$3,270
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$3,270
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$3,270
27
28
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 $4,400
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$4,400
4
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$4,400
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$4,400
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$4,400
25
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$4,800
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
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$4,900
8
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$4,900
15
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$4,900
22
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$4,450
29
30
31
 $3,150
September 2027
SuMoTuWeThFrSaWeek
 1
2
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$3,150
5
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$3,150
12
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$2,750
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$2,250
26
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30
 $2,250
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

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