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.

Displaying 16 - 18 of 18

View Result on Map
Depart OnlyArrive OnlyBookedAvailable
Add Favorite
 
<< >>
View Larger Images (22 images)
Get My Quote
SWEET 3-BEDROOM, 3-BATH CHILMARK COTTAGE, SPACIOUS SCREENED PORCH AND DECK AREAS, OUTDOOR SHOWER; PRIVATE LOCATION ON 4 ACRES, 10 MINUTES TO LUCY VINCENT AND LONG POINT BEACHES

Charming updated summer home features a dining room that seats six, well-stocked kitchen, living room, plus screen porch with ceiling fan, dining table and chairs for 8, and reading/lounging nooks, leading...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,300 - $3,300
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
August 2027
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
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, $150 interim cleaning on multiple week rentals
Tax: State & Local: 
11.7
Add Favorite
fennb13-01-exterior.jpg
 
<< >>
View Larger Images (13 images)
Get My Quote

FENNB

Inquire
Property Details
Menemsha, Water View, Walk to beach
Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,950 - $3,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$1,950
6
7
8
9
10
11
12
$1,950
13
14
15
16
17
18
19
$1,950
20
21
22
23
24
25
26
$1,950
27
28
29
30
 $3,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,000
4
5
6
7
8
9
10
$3,000
11
12
13
14
15
16
17
$3,000
18
19
20
21
22
23
24
$3,000
25
26
27
28
29
30
31
$3,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,200
8
9
10
11
12
13
14
$3,200
15
16
17
18
19
20
21
$3,200
22
23
24
25
26
27
28
$3,200
29
30
31
 $3,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,200
5
6
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: 
$200 per week
Tax: State & Local: 
11.7
Add Favorite
PERRG-1A-Patio.jpg
 
<< >>
View Larger Images (32 images)
Get My Quote

PERRG

Inquire
Property Details
North Slope Hilltop House. Private yard, Screeened Porch and Patio, 8 minute drive to Lucy Vincent Beach or Menemsha Village

Delightful, 3 bedroom, 2 bath home with AC. Private Chilmark hilltop location! This sweet home features an open kitchen, living, and dining area, and a screened porch for your summer...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,600
6
7
8
9
10
11
12
$3,600
13
14
15
16
17
18
19
$3,600
20
21
22
23
24
25
26
$3,800
27
28
29
30
 $3,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,800
4
5
6
7
8
9
10
$3,800
11
12
13
14
15
16
17
$3,800
18
19
20
21
22
23
24
$3,800
25
26
27
28
29
30
31
$4,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$3,800
12
13
14
15
16
17
18
$3,600
19
20
21
22
23
24
25
$3,600
26
27
28
29
30
 $3,600
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Pages