Chilmark Vacation Rentals

Our Chilmark vacation rentals give you direct access to both Vineyard Sound and the Open Ocean. Chilmark is a quiet town of the west side of Martha’s Vineyard with amazing beaches, sanctuaries, and nature preserves. Chilmark has over six beaches, and our many vacation homes place you right on the waterfront. Martha’s Vineyard vacations in Chilmark are full of ocean breezes, kayaking, and secluded beaches.

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Cottage with Screened Porch, Close to Menemsha Village Area and just a Short Drive to Lucy Vincent Beacn

Menemsha Crossroads sweet cottage in a private wooded area, perfect for a family of four. Features 2 bedrooms, a primary with bath, and the 2nd bedroom uses a hall bath. The...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$1,700 - $3,500
June 2026
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$2,500
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$2,500
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 $3,000
July 2026
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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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 $3,000
August 2026
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$3,000
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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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 $2,500
September 2026
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$2,500
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$2,500
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 $2,500
Clean Fee: 
$300 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
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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30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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FENNB

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Property Details
Menemsha, Water View, Walk to beach
Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,950 - $3,200
June 2026
SuMoTuWeThFrSaWeek
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$1,950
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$1,950
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$1,950
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$1,950
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 $3,000
July 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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 $3,200
August 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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$3,200
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 $1,950
September 2026
SuMoTuWeThFrSaWeek
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$1,950
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$1,950
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$1,950
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$1,950
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 $1,950
Clean Fee: 
$200 per week
Tax: State & Local: 
11.7
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PLACH

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Property Details

Note:  Pool is heated by solar panels so the temperature cannot be set. Generally is in the 80's during the latter part of June through the first week of September.  ...Read more

Location: 
Chilmark
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$0 - $0
June 2026
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Clean Fee: 
$800 per week
Tax: State & Local: 
11.7

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