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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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 - $3,200
June 2025
SuMoTuWeThFrSaWeek
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2
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$3,000
8
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$3,000
15
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$3,000
22
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$3,000
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
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10
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$3,500
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$3,500
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25
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$3,500
27
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31
 $3,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,500
3
4
5
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$3,500
10
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$3,500
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18
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$3,500
24
25
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29
30
$3,500
31
 $3,200
September 2025
SuMoTuWeThFrSaWeek
 1
2
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$3,200
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8
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$3,200
14
15
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$3,200
21
22
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27
$3,200
28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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WATTL

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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 - $3,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,100
8
9
10
11
12
13
14
$2,100
15
16
17
18
19
20
21
22
23
24
25
26
27
28
$2,400
29
30
 $2,700
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,700
6
7
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$2,700
13
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$2,700
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$2,800
27
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30
31
 $3,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,000
3
4
5
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$3,000
10
11
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$3,000
17
18
19
20
21
22
23
$3,000
24
25
26
27
28
29
30
$2,600
31
 $1,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$1,700
7
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$1,700
14
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20
$1,700
21
22
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24
25
26
27
$1,700
28
29
30
 
Clean Fee: 
$300 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 2025
SuMoTuWeThFrSaWeek
1
2
3
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7
$25,000
8
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$25,000
15
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$30,000
22
23
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28
$30,000
29
30
 $40,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$40,000
6
7
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12
$40,000
13
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$40,000
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21
22
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$40,000
27
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30
31
 $40,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$40,000
3
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$40,000
10
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$40,000
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$40,000
24
25
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27
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29
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$40,000
31
 $30,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$30,000
7
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$30,000
14
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$25,000
21
22
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27
$25,000
28
29
30
 $25,000
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 2025
SuMoTuWeThFrSaWeek
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$35,000
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$35,000
15
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$35,000
22
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$40,000
29
30
 $55,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
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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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30
31
 $60,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$60,000
3
4
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6
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$60,000
10
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$60,000
17
18
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20
21
22
23
$55,000
24
25
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27
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29
30
$50,000
31
 $35,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$35,000
7
8
9
10
11
12
13
$30,000
14
15
16
17
18
19
20
$30,000
21
22
23
24
25
26
27
$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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