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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 - $9,350
June 2026
SuMoTuWeThFrSaWeek
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$12,400
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$13,600
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$14,500
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$16,650
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 $16,650
July 2026
SuMoTuWeThFrSaWeek
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$16,650
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$17,250
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$17,250
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$17,250
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 $17,850
August 2026
SuMoTuWeThFrSaWeek
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$17,850
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$17,850
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$17,850
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$15,130
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$13,900
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 $12,700
September 2026
SuMoTuWeThFrSaWeek
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$12,700
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$11,650
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$10,300
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$9,100
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 $8,150
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 - $6,800
June 2026
SuMoTuWeThFrSaWeek
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$3,800
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$3,800
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$3,800
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$5,500
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 $6,300
July 2026
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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 $6,800
August 2026
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
30
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 $5,820
September 2026
SuMoTuWeThFrSaWeek
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$5,820
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$3,800
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$3,800
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$3,800
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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 2026
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July 2026
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August 2026
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September 2026
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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 - $3,900
June 2026
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July 2026
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August 2026
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September 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
SuMoTuWeThFrSaWeek
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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
SuMoTuWeThFrSaWeek
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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
SuMoTuWeThFrSa
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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

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:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$12,000
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 $15,000
July 2026
SuMoTuWeThFrSaWeek
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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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 $15,000
August 2026
SuMoTuWeThFrSaWeek
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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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$12,000
30
31
 
September 2026
SuMoTuWeThFrSa
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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:
$15,600 - $15,600
June 2026
SuMoTuWeThFrSaWeek
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 $15,600
July 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
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
30
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September 2026
SuMoTuWeThFrSa
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Clean Fee: 
$875 per rental period
Tax: State & Local: 
11.7
Add Favorite
 
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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:
$6,500 - $6,500
June 2026
SuMoTuWeThFrSa
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July 2026
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August 2026
SuMoTuWeThFrSaWeek
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$8,500
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$8,500
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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
Add Favorite
 
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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:
$3,000 - $7,500
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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 $4,500
July 2026
SuMoTuWeThFrSaWeek
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$4,500
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$5,000
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$4,500
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$4,500
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 $4,500
August 2026
SuMoTuWeThFrSaWeek
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$4,500
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$7,500
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$7,500
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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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$3,000
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$3,000
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$3,000
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30
 $3,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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
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
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: 
$300 per week
Tax: State & Local: 
11.7

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