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Newly Refurbished Contemporary Home, Beautifully Furnished, Privately Situated with Large Yard and Wraparound Farmer’s Porch, Dodger’s Hole Area

A great vacation begins with a great vacation home. This spacious home set on a private, large landscaped lot is sure to please. The summer wrap around porch is the perfect...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$6,550 - $7,150
June 2025
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$6,950
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$6,950
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 $7,150
August 2025
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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
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 $6,550
September 2025
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$6,550
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$6,550
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$6,550
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$6,550
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Transferrable ferry tickets available 8/23-8/30. Please inquire for details! (mv)

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MCDNA

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Property Details
Quintessential Village Center Home, Multiple Indoor/Outdoor Living Spaces, 3 Minute Walk to Main St, 4 bedrooms, Sleeps 8

Charming Village Center Cape-Style Home in Edgartown

Tucked just off Main Street in the heart of Edgartown, this sweet and pristine Cape-style home offers the perfect blend of charm and...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,690 - $7,090
June 2025
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July 2025
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$8,990
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$8,990
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 $9,190
August 2025
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$9,190
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$9,780
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$9,780
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$9,780
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$8,190
31
 $7,090
September 2025
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$7,090
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$5,790
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$5,090
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$4,390
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29
30
 $3,690
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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BURBS

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Property Details
Set Just on the ouskirts of Oak Bluffs. Central AC, Screened Porch

Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs center and beach area.  Fully furnished screen porch and shady porch.  This lovely home sleeps families of 8 comfortably.

The main...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,500 - $7,000
June 2025
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July 2025
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$5,500
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$5,500
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 $6,000
August 2025
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$6,000
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Clean Fee: 
$425 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:
$3,000 - $7,000
June 2025
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July 2025
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$6,500
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$5,500
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 $6,500
August 2025
SuMoTuWeThFrSaWeek
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$6,500
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$6,500
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$6,000
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$7,000
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$5,000
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 $4,000
September 2025
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$4,000
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$4,000
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$4,000
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$3,000
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29
30
 $3,000
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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DONAK

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Property Details
Stunning Luxury Home, Complete Renovation in Main House, Sweet Updated Guest House, Walk to Oak Bluffs Center

Gorgeous Luxury Home, Newly Renovated with Stylish Updates, Walking Distance to Oak Bluffs Center

This stunning bungalow-style home has undergone a complete renovation, blending luxury designer decor with the original...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$7,000 - $7,000
June 2025
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July 2025
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$9,000
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$9,000
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 $15,000
August 2025
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$15,000
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$17,000
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$17,000
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$12,000
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$10,000
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 $7,000
September 2025
SuMoTuWeThFrSaWeek
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$7,000
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$7,000
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$7,000
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$7,000
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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HANRJ

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Property Details
Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes

Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $7,000
June 2025
SuMoTuWeThFrSa
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July 2025
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$6,000
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$4,500
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 $5,500
August 2025
SuMoTuWeThFrSaWeek
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2
$5,500
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$5,500
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$7,000
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$7,000
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$5,500
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 $5,000
September 2025
SuMoTuWeThFrSaWeek
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$5,000
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$4,000
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$4,000
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$4,000
28
29
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 $3,500
Clean Fee: 
$575
Tax: State & Local: 
11.7

Owner reduced rates for available weeks in June, July & August - see calendar for adjusted rates

 

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HOL14

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Property Details
Gorgeous Waterfront Home on the Lagoon Oak Bluffs, Kayak, Swim, Enjoy the Sunsets, 4 bedrooms 4.5 Baths

Stunning Waterfront home nestled just in the outskirts of Oak Bluffs, 1 mile from town center and Oak Bluffs beaches. This home offers 150 feet of private lagoon beach perfect...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,000 - $7,000
June 2025
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July 2025
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$11,500
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$11,500
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 $15,800
August 2025
SuMoTuWeThFrSaWeek
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$15,800
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$15,800
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$15,800
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$15,800
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$15,800
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 $9,500
September 2025
SuMoTuWeThFrSaWeek
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$9,500
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$9,000
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$7,000
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$7,000
28
29
30
 $7,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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CAROB

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Property Details
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:
$3,000 - $7,000
June 2025
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July 2025
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$6,250
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$7,000
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 $5,900
August 2025
SuMoTuWeThFrSaWeek
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$5,900
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$6,500
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$7,000
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$7,000
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$6,000
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 $4,500
September 2025
SuMoTuWeThFrSaWeek
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$4,500
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$3,200
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$3,200
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$3,200
28
29
30
 $3,000
Clean Fee: 
$550 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 2025
SuMoTuWeThFrSa
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July 2025
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$5,600
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$5,900
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 $5,900
August 2025
SuMoTuWeThFrSaWeek
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$5,900
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$6,200
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$6,700
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$6,700
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$5,700
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 $3,900
September 2025
SuMoTuWeThFrSaWeek
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$3,900
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$3,200
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30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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WEINS

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Property Details
Charming and Pristine Hilltop Restored Farm House, Water views, Spectacular Sunsets, Set on Large Private Acreage

Hilltop House is located on one of the highest points on the Island displaying broad views across the rolling hills to beautiful water views beyond. Acres of undisturbed privacy and a...Read more

Location: 
Aquinnah
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$6,800 - $6,800
June 2025
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July 2025
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$6,800
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 $6,800
August 2025
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
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 $6,800
September 2025
SuMoTuWeThFrSaWeek
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$6,800
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30
 
Clean Fee: 
$350 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:
$3,900 - $6,800
June 2025
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July 2025
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$6,800
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$6,800
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August 2025
SuMoTuWeThFrSaWeek
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$6,800
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 $3,900
September 2025
SuMoTuWeThFrSaWeek
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$3,900
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$3,900
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$3,900
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27
28
29
30
 
Clean Fee: 
$425 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 2025
SuMoTuWeThFrSa
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July 2025
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$6,000
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$6,000
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28
29
30
31
 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,000
3
4
5
6
7
8
9
$6,000
10
11
12
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$6,000
17
18
19
20
21
22
23
$6,000
24
25
26
27
28
29
30
$6,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
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13
$4,000
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PE585

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Property Details
Perfect Beach Front Cottage. Expansive Water Views, Gorgeous Sunsets, Pristine Modern Interior

Privately nestled atop a dune with breathtaking views and just steps from a private swimming beach. This immaculate 2 bedroom, 1 bath beachfront cottage offers a tastefully furnished interior with sun-filled rooms...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$4,250 - $6,750
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
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12
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14
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19
$6,750
20
21
22
23
24
25
26
$6,750
27
28
29
30
31
 $6,750
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,750
3
4
5
6
7
8
9
$6,750
10
11
12
13
14
15
16
$6,750
17
18
19
20
21
22
23
$6,750
24
25
26
27
28
29
30
$6,250
31
 $5,750
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,750
7
8
9
10
11
12
13
$5,250
14
15
16
17
18
19
20
$4,750
21
22
23
24
25
26
27
$4,750
28
29
30
 $4,250
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Transferrable ferry ticket available 8/23-8/30. Please inquire for details! (mv)

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MILLD

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Property Details
Green Home, Private Location, AC, Screened Porch, Patio, Short Drive to Gorgeous West Tisbury Beaches

Contemporary West Tisbury home in a private setting yet only minutes to beautiful beaches. The open airy floor plan and gourmet kitchen create a wonderful gathering area for vacationing families....Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$3,000 - $6,500
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
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20
21
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27
28
29
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
31
 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,000
3
4
5
6
7
8
9
$6,500
10
11
12
13
14
15
16
$6,500
17
18
19
20
21
22
23
$6,500
24
25
26
27
28
29
30
$6,500
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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LECAY

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Property Details
Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bedrooms, 15 Minute Walk to Oak Bluffs Center and Inkwell Beach

All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, all just a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,500 - $6,500
June 2025
SuMoTuWeThFrSa
1
2
3
4
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
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12
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,000
3
4
5
6
7
8
9
$8,000
10
11
12
13
14
15
16
$8,000
17
18
19
20
21
22
23
$8,000
24
25
26
27
28
29
30
$6,500
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

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