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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Designer Luxury with Oustanding Atlantic Ocean Views, Private Beaches, Squibnocket Farm Gated Community

Dramatic ocean views, idyllic one-of-a-kind location in a gated community, and private ocean beaches are but a few of the desirable features of this beautiful 5 bedroom, 5 bath contemporary home,...Read more

Location: 
Chilmark
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$10 - $45,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$35,000
8
9
10
11
12
13
14
$35,000
15
16
17
18
19
20
21
$35,000
22
23
24
25
26
27
28
$35,000
29
30
 $40,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$40,000
6
7
8
9
10
11
12
$40,000
13
14
15
16
17
18
19
$40,000
20
21
22
23
24
25
26
$40,000
27
28
29
30
31
 $45,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$45,000
3
4
5
6
7
8
9
$45,000
10
11
12
13
14
15
16
$45,000
17
18
19
20
21
22
23
$45,000
24
25
26
27
28
29
30
$45,000
31
 $45,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$45,000
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: 
$600 per week
Tax: State & Local: 
11.7
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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:
$10 - $40,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$25,000
8
9
10
11
12
13
14
$25,000
15
16
17
18
19
20
21
$30,000
22
23
24
25
26
27
28
$30,000
29
30
 $40,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$40,000
6
7
8
9
10
11
12
$40,000
13
14
15
16
17
18
19
$40,000
20
21
22
23
24
25
26
$40,000
27
28
29
30
31
 $40,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$40,000
3
4
5
6
7
8
9
$40,000
10
11
12
13
14
15
16
$40,000
17
18
19
20
21
22
23
$40,000
24
25
26
27
28
29
30
$40,000
31
 $30,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$30,000
7
8
9
10
11
12
13
$30,000
14
15
16
17
18
19
20
$25,000
21
22
23
24
25
26
27
$25,000
28
29
30
 $25,000
Clean Fee: 
$800 per week
Tax: State & Local: 
11.7
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Ocean View House! Luxury Main & Guest, Waterfront on the Vineyard Sound, Association Beach, 5 Bedrooms, 3 Baths

Stunning Spring Point Vacation Retreat! This newly renovated Main & Guest House is situated in a 335 acre parcel of Chilmark with approximately 40 homes scattered throughout the acreage, and is...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$10 - $30,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$18,000
8
9
10
11
12
13
14
$18,000
15
16
17
18
19
20
21
$18,000
22
23
24
25
26
27
28
$22,000
29
30
 $22,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$22,000
6
7
8
9
10
11
12
$22,000
13
14
15
16
17
18
19
$22,000
20
21
22
23
24
25
26
$22,000
27
28
29
30
31
 $30,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$30,000
3
4
5
6
7
8
9
$30,000
10
11
12
13
14
15
16
$30,000
17
18
19
20
21
22
23
$30,000
24
25
26
27
28
29
30
$30,000
31
 $25,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$25,000
7
8
9
10
11
12
13
$16,000
14
15
16
17
18
19
20
$15,000
21
22
23
24
25
26
27
$15,000
28
29
30
 $12,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Heated Pool, Stone Patio, Pool Pavillion, Propane Fire Pit, Set on 7.5 private acres

New for 2024: Heated Pool with Patio Surround, Propane Fire Pit,  Post and Beam Pool Pavillion with outdoor kitchen hosting 36" Lynx Grill,  Lynx Sink, Power Burner, undercounter Fridge and dishwasher, Raised...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $25,000
June 2025
SuMoTuWeThFrSaWeek
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
$18,500
29
30
 $20,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$20,500
6
7
8
9
10
11
12
$20,500
13
14
15
16
17
18
19
$22,500
20
21
22
23
24
25
26
$22,500
27
28
29
30
31
 $25,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$25,000
3
4
5
6
7
8
9
$25,000
10
11
12
13
14
15
16
$25,000
17
18
19
20
21
22
23
$25,000
24
25
26
27
28
29
30
$25,000
31
 $20,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$20,500
7
8
9
10
11
12
13
$18,500
14
15
16
17
18
19
20
$18,500
21
22
23
24
25
26
27
$18,500
28
29
30
 
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

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

 

Pool Heated to 82 degrees June & Sept weeks $300/week 

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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:
$10 - $13,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,350
8
9
10
11
12
13
14
$7,350
15
16
17
18
19
20
21
$8,000
22
23
24
25
26
27
28
$12,400
29
30
 $13,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$13,000
6
7
8
9
10
11
12
$13,000
13
14
15
16
17
18
19
$13,000
20
21
22
23
24
25
26
$13,000
27
28
29
30
31
 $13,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$13,500
3
4
5
6
7
8
9
$13,500
10
11
12
13
14
15
16
$13,500
17
18
19
20
21
22
23
$13,500
24
25
26
27
28
29
30
$13,000
31
 $8,300
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,300
7
8
9
10
11
12
13
$7,650
14
15
16
17
18
19
20
$7,650
21
22
23
24
25
26
27
$7,650
28
29
30
 $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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Stately Historic Chilmark Home, All Newly updated to Luxury Standards, Private Association South Shore Beach Rights, Hancock Beach 1.5 miles from House

This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach!  The house lies between West Tisbury (Alley’s General Store, 7A...Read more

Location: 
Chilmark
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$10 - $12,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,000
8
9
10
11
12
13
14
$7,000
15
16
17
18
19
20
21
$7,000
22
23
24
25
26
27
28
$7,000
29
30
 $10,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
31
 $12,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$12,000
3
4
5
6
7
8
9
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$12,000
24
25
26
27
28
29
30
$10,000
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$7,000
28
29
30
 $5,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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Chilmark, Charming Updated Menemsha Home. Water Views & Sunset Views, Quintessential Beach House.

On a hilltop overlooking the ocean in Menemsha sits this authentic Vineyard home. From one of the most desirable locations on the island, it's an easy walk to the...Read more

Location: 
Chilmark
Sleeps: 
7
Bedrooms: 
4
Price Range:
$10 - $11,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,000
8
9
10
11
12
13
14
$10,000
15
16
17
18
19
20
21
$10,000
22
23
24
25
26
27
28
$10,500
29
30
 $11,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,000
6
7
8
9
10
11
12
$11,000
13
14
15
16
17
18
19
$11,000
20
21
22
23
24
25
26
$11,000
27
28
29
30
31
 $11,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$11,000
3
4
5
6
7
8
9
$11,000
10
11
12
13
14
15
16
$11,000
17
18
19
20
21
22
23
$11,000
24
25
26
27
28
29
30
$11,000
31
 $10,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$10,000
7
8
9
10
11
12
13
$10,000
14
15
16
17
18
19
20
$9,000
21
22
23
24
25
26
27
$9,000
28
29
30
 $8,000
Clean Fee: 
$500
Tax: State & Local: 
11.7
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Spectacular Chilmark Sunset Water Views, Walk to Private Associaton Waterfont on the North Shore, Association Tennis and the many Walking Trails.

This charming, updated cottage is located on Chilmark's iconic north shore with views of Vineyard Sound and the Elizabeth Islands.  Take in spectacular sunset water views from the 40-foot deck...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $9,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,500
8
9
10
11
12
13
14
$5,500
15
16
17
18
19
20
21
$5,500
22
23
24
25
26
27
28
$5,500
29
30
 $5,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$8,500
13
14
15
16
17
18
19
$8,500
20
21
22
23
24
25
26
$8,500
27
28
29
30
31
 $8,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,500
3
4
5
6
7
8
9
$9,500
10
11
12
13
14
15
16
$9,500
17
18
19
20
21
22
23
$9,500
24
25
26
27
28
29
30
$8,500
31
 $5,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,500
7
8
9
10
11
12
13
$5,000
14
15
16
17
18
19
20
$5,000
21
22
23
24
25
26
27
$5,000
28
29
30
 $5,000
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7

This home books Fri to Fri in July & August

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Menemsha

Magical Menemsha Cottage with water views of the Elizabeth Islands and harbor. The wooded property encompasses 3 private acres and is within walking distance to the village of Menemsha and...Read more

Location: 
Chilmark
Sleeps: 
7
Bedrooms: 
3
Baths: 
1
Price Range:
$10 - $8,220
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,750
8
9
10
11
12
13
14
$5,750
15
16
17
18
19
20
21
$5,750
22
23
24
25
26
27
28
$5,750
29
30
 $7,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
31
 $8,220
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,220
3
4
5
6
7
8
9
$8,220
10
11
12
13
14
15
16
$8,220
17
18
19
20
21
22
23
$8,220
24
25
26
27
28
29
30
$8,220
31
 $6,030
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,030
7
8
9
10
11
12
13
$6,030
14
15
16
17
18
19
20
$6,030
21
22
23
24
25
26
27
$6,030
28
29
30
 $4,050
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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Menemsha Waterfront, Magnificent Views and Private Location, WiFi

This quintessential Chilmark cottage/home has been impeccably maintained,  The dining and living areas with spectacular views across Menemsha Channel to Aquinnah open to a wrap-around deck.  Enjoy spectacular water views...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $7,700
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$5,500
15
16
17
18
19
20
21
$5,500
22
23
24
25
26
27
28
$7,500
29
30
 $7,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$7,700
20
21
22
23
24
25
26
$7,700
27
28
29
30
31
 $7,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,500
3
4
5
6
7
8
9
$7,500
10
11
12
13
14
15
16
$7,500
17
18
19
20
21
22
23
$7,500
24
25
26
27
28
29
30
$7,500
31
 $5,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,500
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
$5,500
28
29
30
 $4,000
Clean Fee: 
$375 per week, owner will provide sheets, towels, beach towels, additional $225 per rental period
Tax: State & Local: 
11.7

Owner will provide, sheets, towels & beach towels for an additional $225 per rented period. 

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Newly Updated Chilmark Cottage, Key to Private association Black Point Beach just 8/10ths mile from Cottage

For those who love Chilmark! Located in a very private setting off of Quenames Rd, this fresh and modern updated cottage comes with a key to private association Black Point...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$10 - $6,600
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $5,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
31
 $5,750
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,750
3
4
5
6
7
8
9
$5,750
10
11
12
13
14
15
16
$5,750
17
18
19
20
21
22
23
$5,750
24
25
26
27
28
29
30
$5,750
31
 $5,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
7
8
9
10
11
12
13
$5,000
14
15
16
17
18
19
20
$6,600
21
22
23
24
25
26
27
$6,600
28
29
30
 $3,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Waterfront, Water View, Walk to Beach

Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $4,700
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,700
8
9
10
11
12
13
14
$3,700
15
16
17
18
19
20
21
$3,700
22
23
24
25
26
27
28
$4,700
29
30
 $4,700
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,700
13
14
15
16
17
18
19
$4,700
20
21
22
23
24
25
26
$4,700
27
28
29
30
31
 $4,700
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,700
3
4
5
6
7
8
9
$4,700
10
11
12
13
14
15
16
$4,700
17
18
19
20
21
22
23
$4,700
24
25
26
27
28
29
30
$4,700
31
 $3,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,700
7
8
9
10
11
12
13
$3,700
14
15
16
17
18
19
20
$3,700
21
22
23
24
25
26
27
$3,700
28
29
30
 $3,000
Clean Fee: 
$300 per week, owner will provide sheets, towels, beach towels, additional $225 per rental period
Tax: State & Local: 
11.7
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PERRG-1A-Patio.jpg
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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:
$10 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
$3,600
15
16
17
18
19
20
21
$3,600
22
23
24
25
26
27
28
$3,800
29
30
 $3,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,800
6
7
8
9
10
11
12
$3,800
13
14
15
16
17
18
19
$3,800
20
21
22
23
24
25
26
$3,800
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
12
13
14
15
16
$4,000
17
18
19
20
21
22
23
$4,000
24
25
26
27
28
29
30
$4,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
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: 
$450 per week
Tax: State & Local: 
11.7
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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:
$10 - $3,780
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,420
29
30
 $3,580
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,580
6
7
8
9
10
11
12
$3,580
13
14
15
16
17
18
19
$3,580
20
21
22
23
24
25
26
$3,580
27
28
29
30
31
 $3,780
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,780
3
4
5
6
7
8
9
$3,780
10
11
12
13
14
15
16
$3,780
17
18
19
20
21
22
23
$3,780
24
25
26
27
28
29
30
$3,780
31
 $3,320
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,320
7
8
9
10
11
12
13
$3,320
14
15
16
17
18
19
20
$2,830
21
22
23
24
25
26
27
$2,830
28
29
30
 
Clean Fee: 
$300 per week, $200 interim cleaning on multiple week rentals
Tax: State & Local: 
11.7
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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:
$10 - $3,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,000
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
31
 $3,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,500
3
4
5
6
7
8
9
$3,500
10
11
12
13
14
15
16
$3,500
17
18
19
20
21
22
23
$3,500
24
25
26
27
28
29
30
$3,500
31
 $3,200
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,200
7
8
9
10
11
12
13
$3,200
14
15
16
17
18
19
20
$3,200
21
22
23
24
25
26
27
$3,200
28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7

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