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:
$10 - $3,200
June 2025
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
29
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 $3,000
July 2025
SuMoTuWeThFrSaWeek
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$3,000
6
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$2,500
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$3,000
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$3,000
27
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 $3,200
August 2025
SuMoTuWeThFrSaWeek
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2
$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
31
 $1,950
September 2025
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
28
29
30
 $1,950
Clean Fee: 
$200 per week
Tax: State & Local: 
11.7
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WATTL

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Property Details
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:
$10 - $2,900
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$1,550
8
9
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$1,750
15
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20
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$1,750
22
23
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25
26
27
28
$2,300
29
30
 $2,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
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$2,600
6
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$2,600
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$2,600
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$2,700
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 $2,900
August 2025
SuMoTuWeThFrSaWeek
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$2,900
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$2,900
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$2,900
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$2,900
24
25
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27
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29
30
$2,500
31
 $1,600
September 2025
SuMoTuWeThFrSaWeek
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$1,600
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$1,600
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$1,600
21
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$1,600
28
29
30
 
Clean Fee: 
$275 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:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
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$35,000
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$35,000
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$35,000
22
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$40,000
29
30
 $55,000
July 2025
SuMoTuWeThFrSaWeek
 1
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$55,000
6
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$50,000
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$50,000
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$50,000
27
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 $60,000
August 2025
SuMoTuWeThFrSaWeek
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$60,000
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$60,000
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$60,000
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$55,000
24
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$50,000
31
 $35,000
September 2025
SuMoTuWeThFrSaWeek
 1
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$35,000
7
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$30,000
14
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$30,000
21
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$30,000
28
29
30
 
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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