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East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

East Chop Escape with lovely Distant Water Views
Light-Filled Tri-Level Home, 4 Bedrooms, & 3 baths, 1.5 Miles to Oak Bluffs Center

Set in the highly sought-after East Chop neighborhood,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $7,150
June 2027
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 $7,150
July 2027
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$7,150
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$7,150
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$7,150
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$7,150
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$7,150
August 2027
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$7,150
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$7,150
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$7,150
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$7,150
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 $7,000
September 2027
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$7,000
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$6,500
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$6,500
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$6,500
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 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45
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BLACJ

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Property Details
Long Point Beach House, All New Primary Suite, Expansive Sun Porch with Living and Dining Areas, Expansive Deck, Private Yard

This Beach-chic Long Point retreat has just undergone an update in most areas with an all-new Primary Bedroom suite and expansive sun porch hosting both living and dining areas and decorated in nautical...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $7,000
June 2027
SuMoTuWeThFrSaWeek
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 $7,000
July 2027
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$7,000
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$7,000
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$7,500
August 2027
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$7,500
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$8,000
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$8,000
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$8,000
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 $7,500
September 2027
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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MCNAB

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Property Details
Spacious Tri Level, Contemporary Home, Located just 1.5 Miles to Edgartown Village Center

This delightful tri-level post and beam home is set in a neighborhood just on the outskirts of the Village area. 1.5 miles to town center, 10-minute drive to State and...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,000 - $7,000
June 2027
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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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 $5,000
July 2027
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$5,000
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$6,500
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$6,500
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$6,500
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$6,500
August 2027
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$6,700
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$7,000
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$7,000
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$5,000
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September 2027
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Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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MCCAM

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Property Details
Stylish New Home, In Village Location, Patio Area with Outdoor Living and Dining, Walk to town!

This beautiful four-bedroom home boasts an open-concept living space, including a large kitchen and dining area, as well as a sitting area with a wet bar, beverage cooler and large...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$7,000 - $7,000
June 2027
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July 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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SIM21

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Property Details
Edgartown Village Center Home, Walk to Town, 2 Bedrooms, 2 Baths

Experience all that Edgartown Village Center has to offer, just a short stroll from this bright and airy home. Additional décor and deck furniture will be added for summer 2025....Read more

Location: 
Edgartown
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$4,500 - $7,000
June 2027
SuMoTuWeThFrSaWeek
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$4,500
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$4,500
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$5,000
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$5,000
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 $6,400
July 2027
SuMoTuWeThFrSaWeek
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$6,400
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$6,400
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$6,400
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$6,400
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$6,400
August 2027
SuMoTuWeThFrSaWeek
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$7,000
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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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$4,500
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$4,500
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$4,500
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 $4,500
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
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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 - $6,950
June 2027
SuMoTuWeThFrSaWeek
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$4,850
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$4,850
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$4,850
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$6,950
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 $6,950
July 2027
SuMoTuWeThFrSaWeek
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$6,950
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$6,950
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$6,950
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$6,950
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$6,950
August 2027
SuMoTuWeThFrSaWeek
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$6,950
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$6,950
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$6,950
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$6,950
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 $6,950
September 2027
SuMoTuWeThFrSaWeek
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$6,950
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$4,000
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$4,000
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$4,000
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30
 $4,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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
SuMoTuWeThFrSaWeek
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2
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$3,800
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$3,800
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$3,800
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$3,800
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 $6,400
July 2027
SuMoTuWeThFrSaWeek
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$6,400
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$6,400
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$6,400
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$6,400
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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
SuMoTuWeThFrSaWeek
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$6,900
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$3,800
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$3,800
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$3,800
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30
 $3,800
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
Add Favorite
 
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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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28
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30
 $5,900
July 2027
SuMoTuWeThFrSaWeek
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2
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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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30
 $4,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
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NORTO

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Property Details
In-Town, Water View, Waterfront

Enjoy expansive harbor views and passing tall-masted schooners from the breezy wrap-around porch of this delightful five-bedroom classic Vineyard home over the harbor. Stroll to the village center, tennis, fine,...Read more

Location: 
Vineyard Haven
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,500 - $6,750
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
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$5,500
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$5,500
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$5,500
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 $6,750
July 2027
SuMoTuWeThFrSaWeek
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2
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$6,750
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$6,750
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$6,750
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$6,750
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$6,750
August 2027
SuMoTuWeThFrSaWeek
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$6,750
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$6,750
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$6,750
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$6,750
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 $5,500
September 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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29
30
 $5,500
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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2
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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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30
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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
26
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28
29
30
 $5,600
Clean Fee: 
$350 per week
Tax: State & Local: 
14.45
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
 1
2
3
4
5
6
7
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9
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12
$4,950
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14
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$4,950
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$4,950
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28
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 $5,300
July 2027
SuMoTuWeThFrSaWeek
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2
3
$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
29
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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: 
14.45
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
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: 
$275 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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:
$4,000 - $6,500
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
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7
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$4,000
13
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$4,000
20
21
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23
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$4,500
27
28
29
30
 $5,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,500
4
5
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$6,500
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$6,500
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$6,500
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$6,500
August 2027
SuMoTuWeThFrSaWeek
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2
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$7,500
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$8,800
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$8,800
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$7,500
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 $5,500
September 2027
SuMoTuWeThFrSaWeek
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2
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$5,500
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$4,000
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$4,000
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$4,000
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29
30
 $4,000
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45
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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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2
3
4
5
$3,400
6
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$3,400
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$4,000
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23
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$5,100
27
28
29
30
 $5,400
July 2027
SuMoTuWeThFrSaWeek
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2
3
$5,400
4
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$5,800
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$6,200
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$6,200
25
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$6,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
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$6,500
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$6,500
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$6,500
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$5,200
29
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 $4,800
September 2027
SuMoTuWeThFrSaWeek
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2
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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
Add Favorite
 
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ROS22

Inquire
Property Details

Set in the heart of Oak Bluffs and on a quiet residential street, this newly updated tastefully decorated vacation home offers rental guests all the comforts of home inside and out....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $6,500
June 2027
SuMoTuWeThFrSaWeek
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2
3
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$4,500
6
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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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$5,500
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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$6,500
29
30
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 $5,000
September 2027
SuMoTuWeThFrSaWeek
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2
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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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 $5,000
Clean Fee: 
$380 per week
Tax: State & Local: 
14.45

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