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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Menemsha, Water View, Walk to beach
Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,950 - $3,200
June 2026
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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
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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
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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
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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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BERNC

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Property Details
Mini Retreat with Pool, Private Peaceful Chilmark Location, Lucy Vincent and Menemsha Beaches Nearby.

Impeccably maintained and updated, this adorable summer home is perfect for families looking for luxury features such as quality linens in a quiet location. The 12 by 18-foot spa pool is...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
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$7,350
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$7,350
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$8,000
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$12,400
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 $13,000
July 2026
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$13,000
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$13,000
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$13,000
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$13,000
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 $13,500
August 2026
SuMoTuWeThFrSaWeek
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$13,500
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$13,500
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$13,500
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$13,500
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$13,000
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 $8,300
September 2026
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$8,300
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$7,650
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$7,650
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$7,650
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 $4,800
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Pool heated to 82 degrees included in rental rate July & August

Pool heated to 82 degrees, May, June Sept and October additional $150 per week propane surcharge

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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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August 2026
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September 2026
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Clean Fee: 
$800 per week
Tax: State & Local: 
11.7
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ENGLJ

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Property Details
Exquisite Estate Vacation Retreat, Main & Guest House, Affinity Pool, South Shore Waterviews, Sleeps 12 in 6 Bedrooms, Multiple Living & Entertaining Areas both indoors & out

Outstanding Chilmark Estate tucked on 9.5 private acres with sweeping views of the Atlantic Ocean and Chilmark Pond. This unique contemporary home features a heated infinity pool, screened porch, and expansive deck with...Read more

Location: 
Chilmark
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$0 - $0
June 2026
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$35,000
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$35,000
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$35,000
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$40,000
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 $55,000
July 2026
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$55,000
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$50,000
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$50,000
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$50,000
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 $60,000
August 2026
SuMoTuWeThFrSaWeek
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$60,000
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$60,000
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$60,000
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$60,000
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$50,000
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 $30,000
September 2026
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$30,000
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$30,000
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$30,000
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$30,000
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Clean Fee: 
$2000 per week
Tax: State & Local: 
11.7

Pool heated to 82 degrees in July and August included in rental rate

Pool heated to 82 degrees June & September additional surcharge $350 per week

Pool heated to 82 degrees May & October additional surcharge $450 per week

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