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Beautifully Updated and Newly Furnished, 4 Bedrooms, 3 Baths, Multiple Living Spaces, Centrally Located to Down Island Towns and Beaches.

This charming newly renovated home boasts an airy, open floor plan on the main level featuring a wall of glass sliders that open onto a spacious deck area complete with a...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,500 - $6,500
June 2027
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July 2027
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$6,500
August 2027
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$6,500
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$7,000
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$7,000
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$6,500
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 $4,500
September 2027
SuMoTuWeThFrSaWeek
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$4,500
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$3,500
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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BOOND

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Property Details
Wonderful Vacation Home, East Chop Area of Oak Bluffs, Private Yard, Screened Porch, 4 bedrooms, 2 baths.

Nestled on a quiet street in the idyllic East Chop area of Oak Bluffs, this classic New England summer home offers vacationing families and friends a special place to gather...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,000 - $6,500
June 2027
SuMoTuWeThFrSaWeek
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3
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$4,250
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$4,500
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$4,750
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$5,000
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29
30
 $5,750
July 2027
SuMoTuWeThFrSaWeek
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2
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$5,750
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$6,250
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$6,250
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$6,500
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$6,750
August 2027
SuMoTuWeThFrSaWeek
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$7,250
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$7,000
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$7,000
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$6,500
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 $5,500
September 2027
SuMoTuWeThFrSaWeek
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$5,500
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$5,250
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$4,500
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$4,000
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 $4,000
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45

Linens additonal $250

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BALAR

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Property Details
Vineyard Meadow Farms Home, Close to Gorgeous Long Point Beach, Contemporary Styling, Central AC, Wi-Fi, Private Yard and Deck

 

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Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,400 - $6,490
June 2027
SuMoTuWeThFrSaWeek
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$4,700
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$4,700
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$4,700
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$4,700
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 $4,700
July 2027
SuMoTuWeThFrSaWeek
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$4,700
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$5,490
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$5,490
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$5,490
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$5,490
August 2027
SuMoTuWeThFrSaWeek
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$6,490
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$6,490
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$6,300
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$5,790
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 $5,790
September 2027
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$5,790
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$5,790
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$4,900
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$4,900
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 $4,900
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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WEBSL

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Property Details
Menemsha

Magical Menemsha Cottage with water views of the Elizabeth Islands and harbor. The wooded property encompasses 3 private acres and is within walking distance to the village of Menemsha and...Read more

Location: 
Chilmark
Sleeps: 
7
Bedrooms: 
3
Baths: 
1
Price Range:
$4,350 - $6,310
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: 
$400 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 - $6,300
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,200
6
7
8
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12
$3,500
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$4,800
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$5,600
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 $5,700
July 2027
SuMoTuWeThFrSaWeek
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2
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$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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29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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BEATM

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Property Details
South Beach Contemporary, Light Filled Interior, Screened Porch and Sunny Deck, Conveniently located to Beach and Five minute drive to Edgartown Village Center

Cute contemporary 3 bedroom, 2 bath beach house located on a quiet lane in the heart of Katama. Just a 5-minute drive to South Beach and 2.5 miles from the Edgartown...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,250 - $6,250
June 2027
SuMoTuWeThFrSaWeek
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2
3
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$4,850
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$4,850
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$5,250
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$5,250
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 $6,000
July 2027
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$6,000
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$6,250
August 2027
SuMoTuWeThFrSaWeek
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$6,250
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$6,250
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$6,250
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$6,250
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 $6,000
September 2027
SuMoTuWeThFrSaWeek
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$6,000
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$5,000
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$5,000
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30
 
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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CLEME

Inquire
Property Details
Sweetened Water Farm, 1 Mile from Village Center, Bike or Walk to Town

Lovely 4 bedroom, 2 bath home.  Located just on the outskirts of Edgartown village center on Sweetened Water Farm (an 87-acre horse farm located near Morning Glory Farm).  This spacious...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,500 - $6,200
June 2027
SuMoTuWeThFrSaWeek
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$2,500
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$4,500
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$4,500
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$4,500
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 $5,500
July 2027
SuMoTuWeThFrSaWeek
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2
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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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$5,900
August 2027
SuMoTuWeThFrSaWeek
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$6,200
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$6,200
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$6,200
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$6,200
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 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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$3,000
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$3,000
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$3,000
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 $3,000
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:
$5,000 - $6,060
June 2027
SuMoTuWeThFrSaWeek
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$5,000
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 $5,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$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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LONGK

Inquire
Property Details
Bayes Hill Beauty - Stunning Landscaping, Privately Situated Deck & Patio Association Tennis

Note: Caretaker lives in apartment above the garage. Renter's privacy respected.  Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$6,000 - $6,000
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: 
$450 per week
Tax: State & Local: 
14.45
Add Favorite
 
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FRISD

Inquire
Property Details
Adorable, Chic In -Town Home, Coastal Décor, Central AC, Large Bluestone Patio plus a Farmers Porch for Summer Outdoor Enjoyment

Charming is the description for this newly furnished in-town summer cottage-style home. The house boasts multiple outdoor living spaces, including a large, secluded bluestone patio with an outdoor living room, a patio dining and grill...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $6,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
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5
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$3,800
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$3,900
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$4,600
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28
29
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 $5,100
July 2027
SuMoTuWeThFrSaWeek
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2
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$5,100
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$6,000
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$6,000
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$6,000
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$6,000
August 2027
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$5,000
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31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
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$4,000
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$3,800
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$3,800
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$3,800
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 $3,800
Clean Fee: 
$390 per week
Tax: State & Local: 
11.7
Add Favorite
 
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CENCP

Inquire
Property Details
East Chop Waterfront, Extraordinary Sunsets &Views Across the Sound , Deck directly on the Beach, Casual Interior

Classic, casual beachfront home combines cottage styling with modern amenities. spectacular views, quietly lapping waves right outside your windows, and breathtaking sunsets. Ideally located in the East Chop Area of Oak Bluffs just a short distance...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$6,000 - $6,000
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: 
$480 per week
Tax: State & Local: 
14.45

 

 

 

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DAWKN

Inquire
Property Details
Exquisite Designer Home, 10 minute Walk to Oak Bluffs Town Center, Screened Porch, Patio Dining Area, Landscaped Yard, Professionally Decorated, AC

Quietly nestled on a quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,050 - $6,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$5,300
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$5,300
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$5,300
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$5,400
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29
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 $6,000
July 2027
SuMoTuWeThFrSaWeek
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3
$6,000
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$6,000
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$6,000
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$6,000
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$6,000
August 2027
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$6,000
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 $6,000
September 2027
SuMoTuWeThFrSaWeek
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$6,000
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$5,100
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$5,100
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$5,100
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 $5,100
Clean Fee: 
$350 per week
Tax: State & Local: 
14.45
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INGAE

Inquire
Property Details
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,250 - $6,000
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: 
$500 per week
Tax: State & Local: 
14.45
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GRILJ

Inquire
Property Details
Lovely Custom Post & Beam Home, Tucked on Gorgeous Private Acreage, 1.5 Miles from the Center of Vineyard Haven.

Martha’s Vineyard Vacation Rental – Private Vineyard Haven Retreat

This lovely and spacious Martha’s Vineyard vacation rental offers all the comforts of home in a serene, private setting. Set on...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,700 - $6,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$3,000
6
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$3,000
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$3,000
20
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25
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 $4,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,800
4
5
6
7
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9
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$4,800
11
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$4,800
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19
20
21
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23
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$4,800
25
26
27
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30
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$5,500
August 2027
SuMoTuWeThFrSaWeek
1
2
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$6,000
8
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$6,000
15
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$6,000
22
23
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$5,200
29
30
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 $3,500
September 2027
SuMoTuWeThFrSaWeek
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2
3
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$3,500
5
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$3,000
12
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$3,000
19
20
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25
$3,000
26
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28
29
30
 $3,000
Clean Fee: 
$575
Tax: State & Local: 
11.7
Add Favorite
 
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LISDA

Inquire
Property Details
Charming Saltbox Edgartown Home, Newly Updated , Island Grove Area, 4 Bedroom, 2 bath, Sleeps 7.

Thoughtfully updated contemporary Saltbox-style retreat, tucked away in the desirable Island Grove area of Edgartown. Surrounded by a spacious yard/lawn area & mature plantings, this inviting vacation home offers the perfect blend...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$3,200 - $6,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$3,600
6
7
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$3,600
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$3,600
20
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$4,200
27
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 $5,500
July 2027
SuMoTuWeThFrSaWeek
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2
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$5,500
4
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$5,800
11
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$5,800
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$6,000
25
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$6,000
August 2027
SuMoTuWeThFrSaWeek
1
2
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$7,700
8
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$7,700
15
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$7,700
22
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$6,900
29
30
31
 $4,500
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$4,500
5
6
7
8
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10
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$3,700
12
13
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$3,500
19
20
21
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23
24
25
$3,500
26
27
28
29
30
 $3,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner open to weekday arrival and departure July weeks to accommodate the need for auto ferry tickets. 

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