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Historic 5 Bedroom Home, Newly Updated, Tucked in Historic Center of West Tisbury

Historic Charm in the Heart of Beautiful West Tisbury. This thoughtfully renovated home blends classic character with modern comfort, featuring a beautifully updated kitchen, three stylish baths, and five inviting...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$4,500 - $7,000
June 2027
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owners are also open to weekday arrivals and departures to meet the need for auto ferry tickets. Please inquire to discuss! 

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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 2027
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July 2027
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September 2027
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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FISHJ

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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 - $6,900
June 2027
SuMoTuWeThFrSaWeek
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$5,500
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$5,500
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$5,500
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$5,500
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 $6,900
July 2027
SuMoTuWeThFrSaWeek
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$6,900
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$6,900
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$6,900
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$6,900
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$6,900
August 2027
SuMoTuWeThFrSaWeek
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$6,900
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$6,900
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$6,900
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$6,900
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 $6,900
September 2027
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$6,900
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$5,500
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$5,200
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$5,200
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 $5,200
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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FREE2

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Property Details
Lovely Historic William St Home, Located just one block from Main St. 4 bedrooms, 4 baths

Beautifully renovated Greek Revival home (the Berkshire House) on historic William Street in Vineyard Haven.

This finely crafted home offers vacationing guests spacious living on three levels. The main level...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,900 - $6,900
June 2027
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September 2027
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

 

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MONVH

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Property Details
Quintessential Vineyard Haven Home, Beautifully Furnished, Surrounded by Large Mature Landscaped Yard, Porch Seating, Multiple Living Spaces Within

Classic Vineyard home set on a quiet street of similar homes. Modern interior with multiple living spaces include a large family room centered around the media area with a sectional sofa...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$5,500 - $6,900
June 2027
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July 2027
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September 2027
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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LUSKP

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Property Details
Cozy Cape, Newly Updated Summer 2023, Quiet Private Central Location, 4 Bedrooms, 3 Baths

Enjoy all the comforts of home in this tri-level updated Cape-style home set in a quiet cul de sac and bordered by lovely landscaping and mature oaks.   Multiple living spaces include the...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $6,900
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$3,200
6
7
8
9
10
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$3,500
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14
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16
17
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$4,800
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21
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$5,600
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29
30
 $5,700
July 2027
SuMoTuWeThFrSaWeek
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2
3
$5,700
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$5,700
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$5,700
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$6,000
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$6,000
August 2027
SuMoTuWeThFrSaWeek
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$6,900
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$6,900
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$6,900
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$6,300
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 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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$3,200
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$3,200
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$3,200
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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DELOA

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Property Details
Ramble House, Lovely, Spacious 3 Bedroom, 3 bath Vacation Home. Tucked on a Tranquil Street in Vineyard Haven, Multiple Living Spaces Indoor & Outdoor, Impeccably Maintained.

A tranquil oasis just outside Vineyard Haven and only one mile from the village center, this spacious and inviting three-bedroom, three-bath home is tucked away at the end of a...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$3,500 - $6,900
June 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,000
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 $5,900
July 2027
SuMoTuWeThFrSaWeek
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$5,900
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$5,900
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$5,900
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$5,900
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$6,900
August 2027
SuMoTuWeThFrSaWeek
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$6,900
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$6,900
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$6,900
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$6,900
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 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,000
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 $4,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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BARTE

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Property Details
Lovely In-Town Home, Ideally located 5 Minute Walk to Main St, Bike Paths to South Beach in Front of House, A/C

Traditional home with large fenced-in yard and great location. Extended families seeking walking distance to in-town activities will find this comfortable and attractively furnished home ideally suited. A bike path...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
5
Baths: 
2
Price Range:
$4,000 - $6,800
June 2027
SuMoTuWeThFrSaWeek
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$4,700
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$4,700
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$6,800
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$6,800
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 $6,800
July 2027
SuMoTuWeThFrSaWeek
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$6,800
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$6,800
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$6,800
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$6,800
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$6,800
August 2027
SuMoTuWeThFrSaWeek
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$6,800
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$6,800
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$6,800
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$6,800
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 $4,700
September 2027
SuMoTuWeThFrSaWeek
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$4,700
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$4,000
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$4,000
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$4,000
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 $4,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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WALCN

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Property Details
Lovely Home in Island Grove Area of Edgartown Conveniently Located between South Beach and Edgartown Village. Association Tennis Courts and Pickleball Available to Renters

This recently updated home is tucked in the Island Grove area of Edgartown and is a perfect retreat for families & friends to gather. Located in a desirable neighborhood with access...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,800 - $6,800
June 2027
SuMoTuWeThFrSaWeek
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$5,000
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 $5,500
July 2027
SuMoTuWeThFrSaWeek
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$5,500
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$6,060
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$6,060
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$6,060
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$6,060
August 2027
SuMoTuWeThFrSaWeek
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$6,800
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$6,800
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$6,800
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$6,800
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 $5,000
September 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
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30
 $5,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ARMSA

Inquire
Property Details
Cozy Newly updated Seashore Cottage, East Chop Highlands Area, Farmers Porch and Deck

If you are looking for an immaculate, charming, cottage-style, yet modern home close to Oak Bluffs center, look no further. This recently updated 3 bedroom, 2 bath home features sunny open...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,600 - $6,700
June 2027
SuMoTuWeThFrSaWeek
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$5,600
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$5,600
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$5,600
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$5,600
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 $6,700
July 2027
SuMoTuWeThFrSaWeek
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$6,700
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$6,700
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$6,700
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$6,700
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$6,700
August 2027
SuMoTuWeThFrSaWeek
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$6,700
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$6,700
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$6,700
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$6,700
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 $5,600
September 2027
SuMoTuWeThFrSaWeek
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$5,600
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$5,600
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$5,600
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$5,600
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30
 $5,600
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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DHANM

Inquire
Property Details
Adorable Oak Bluffs Cottage Just Over a Mile to the Village Center and Town Beaches, Porch, Deck, 4 Bedrooms, 2 Baths

Nestled on a quiet street, this recently updated residence boasts delightful indoor and outdoor living areas. The entrance porch offers cozy seating with wicker chairs and a small dining table that...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,950 - $6,700
June 2027
SuMoTuWeThFrSaWeek
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$4,950
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$4,950
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$4,950
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 $5,300
July 2027
SuMoTuWeThFrSaWeek
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$5,300
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$5,500
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$5,500
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$5,500
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$5,500
August 2027
SuMoTuWeThFrSaWeek
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$6,200
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$6,700
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$6,700
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$6,700
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 $6,700
September 2027
SuMoTuWeThFrSaWeek
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$6,700
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29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ELOUA

Inquire
Property Details
Lovely updated Home , Village Area Edgartown, 7 minute Walk to Main St. Bike Paths at end of Street.

Minutes from downtown Edgartown's shops & restaurants, this cape style home features open concept living, air conditioning, a mini-split in the main living area, window units in all but 1st level...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,650 - $6,650
June 2027
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September 2027
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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THORB

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

Perfect for extended families and friends, this spacious tri-level contemporary home offers multiple gathering spaces, comfortable accommodations, and an ideal location just a short stroll from the heart of Oak Bluffs....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,500 - $6,500
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$575 per week
Tax: State & Local: 
11.7

Owner reduced rates for available weeks in July - see calendar for adjusted rates

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CLARA

Inquire
Property Details
Exclusive Makonikey Area Home, Private Landscaped Yard, Large Deck Area, 4 bedrooms & 4 Baths. Short Drive to Towns and Multiple Beaches

Family and friends are sure to enjoy this pristinely maintained and spacious home situated in a private and quiet location. Beautiful yard and deck area with outdoor seating and a patio dining area that...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$4,000 - $6,500
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Sheets & Towels are not provided. Rental guests need to bring sheets & towels, or they can be rented and delivered per the instructions from the linen rental company. www.marthaslinenrental.com

 

 

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PIZZD

Inquire
Property Details
KATAMA AREA, SET ON PRIVATE ACREAGE, SHORT DRIVE TO SOUTH BEACH AND EDGARTOWN VILLAGE CENTER

Extended family will enjoy the comfort and private setting of this large 5 bedroom home in the Katama area of Edgartown.   Spacious for extended family, the kitchen with custom cabinetry and...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$2,400 - $6,500
June 2027
SuMoTuWeThFrSaWeek
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5
$3,400
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$3,400
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$4,000
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$5,100
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 $5,400
July 2027
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$5,400
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$5,800
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$6,000
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$6,200
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$6,500
August 2027
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$6,500
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$6,500
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$6,500
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$5,200
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 $4,800
September 2027
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$4,800
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$3,400
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$3,000
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$3,000
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 $3,000
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

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