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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:
$0 - $0
June 2026
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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:
$5,350 - $7,500
June 2026
SuMoTuWeThFrSaWeek
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 $5,350
July 2026
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$5,350
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$5,350
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$5,350
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$5,350
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 $7,000
August 2026
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$7,000
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$7,000
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$7,200
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$7,500
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September 2026
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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 - $11,000
June 2026
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$12,000
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 $15,000
July 2026
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$15,000
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$15,000
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$15,000
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 $15,000
August 2026
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$15,000
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$15,000
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$15,000
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$15,000
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$11,000
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 $8,000
September 2026
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$8,000
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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
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 $15,600
July 2026
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$15,600
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$15,600
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$15,600
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$15,600
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 $15,600
August 2026
SuMoTuWeThFrSaWeek
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$15,600
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$15,600
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$15,600
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$15,600
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$15,600
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September 2026
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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
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July 2026
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August 2026
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$8,500
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$6,500
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September 2026
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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VANAL

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Property Details
Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,

Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $5,000
June 2026
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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 $5,000
July 2026
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$5,000
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$5,000
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 $5,000
August 2026
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$5,000
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$7,500
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$5,000
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 $4,500
September 2026
SuMoTuWeThFrSaWeek
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$4,500
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$4,500
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$3,500
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$3,500
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 $3,500
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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VANDN

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Property Details
Charming Newly Updated Menemsha Cottage, 2 + Bedroom Cottage Sleeps 5, AC, Screened Porch & Deck, Walk to Menemsha Village & Beach

Dreaming of Vacationing in an idyllic Menemsha Cottage? This adorable newly updated  1950s cottage nestled in the village area provides easy access to numerous exclusive Chilmark beaches with town permits and Menemsha Beach...Read more

Location: 
Chilmark
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$2,500 - $3,500
June 2026
SuMoTuWeThFrSaWeek
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$3,000
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$3,000
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$3,000
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$3,000
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 $3,500
July 2026
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$3,500
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$3,500
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$3,500
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$3,500
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 $3,500
August 2026
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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$3,500
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$3,500
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 $3,200
September 2026
SuMoTuWeThFrSaWeek
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$3,200
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$3,200
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$3,200
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$3,200
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Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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VOL55

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Property Details
LIGHT FILLED CONTEMPORARY HOME, AC, DECK AND SUN PORCH, SLEEPS 8

Set on a quiet circular street (Teaberry Lane), on the outskirts of Edgartown. Bike paths at the end of the street connect to town and miles of touring trails. This...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$4,250 - $4,250
June 2026
SuMoTuWeThFrSaWeek
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 $3,200
July 2026
SuMoTuWeThFrSaWeek
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$3,200
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$3,200
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$4,150
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$4,150
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 $4,150
August 2026
SuMoTuWeThFrSaWeek
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$4,150
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$4,250
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$4,250
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$4,250
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$4,250
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September 2026
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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VOREA

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Property Details
Meeting House Village Condo, Association Pool, Short Drive to Edgartown Center, South Beach & State Beach

Note: Owner is replacing Sofas seen in photos with two new slip covered sofas and will be replacing all bedding and the baths will get a primp as well. New kitchen items...Read more

Location: 
Edgartown
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$0 - $0
June 2026
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Clean Fee: 
$275 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 - $5,280
June 2026
SuMoTuWeThFrSaWeek
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$4,800
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 $5,280
July 2026
SuMoTuWeThFrSaWeek
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$5,280
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$5,770
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$5,770
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$5,770
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 $5,770
August 2026
SuMoTuWeThFrSaWeek
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$5,770
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$6,470
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September 2026
SuMoTuWeThFrSaWeek
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$4,800
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Clean Fee: 
$525 per week
Tax: State & Local: 
11.7

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