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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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:
$30,000 - $60,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$35,000
7
8
9
10
11
12
13
$35,000
14
15
16
17
18
19
20
$35,000
21
22
23
24
25
26
27
$40,000
28
29
30
 $55,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$55,000
5
6
7
8
9
10
11
$50,000
12
13
14
15
16
17
18
$50,000
19
20
21
22
23
24
25
$50,000
26
27
28
29
30
31
 $60,000
August 2026
SuMoTuWeThFrSaWeek
 1
$60,000
2
3
4
5
6
7
8
$60,000
9
10
11
12
13
14
15
$60,000
16
17
18
19
20
21
22
$60,000
23
24
25
26
27
28
29
$50,000
30
31
 $30,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$30,000
6
7
8
9
10
11
12
$30,000
13
14
15
16
17
18
19
$30,000
20
21
22
23
24
25
26
$30,000
27
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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WINGR

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Property Details
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:
$30,000 - $45,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$35,000
7
8
9
10
11
12
13
$35,000
14
15
16
17
18
19
20
$35,000
21
22
23
24
25
26
27
$35,000
28
29
30
 $40,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$40,000
5
6
7
8
9
10
11
$40,000
12
13
14
15
16
17
18
$40,000
19
20
21
22
23
24
25
$40,000
26
27
28
29
30
31
 $45,000
August 2026
SuMoTuWeThFrSaWeek
 1
$45,000
2
3
4
5
6
7
8
$45,000
9
10
11
12
13
14
15
$45,000
16
17
18
19
20
21
22
$45,000
23
24
25
26
27
28
29
$45,000
30
31
 $45,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$45,000
6
7
8
9
10
11
12
$30,000
13
14
15
16
17
18
19
$30,000
20
21
22
23
24
25
26
$30,000
27
28
29
30
 $30,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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SUDRL

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Property Details
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:
$15,000 - $30,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$15,000
7
8
9
10
11
12
13
$15,000
14
15
16
17
18
19
20
$15,000
21
22
23
24
25
26
27
$15,000
28
29
30
 $25,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$25,000
5
6
7
8
9
10
11
$25,000
12
13
14
15
16
17
18
$25,000
19
20
21
22
23
24
25
$25,000
26
27
28
29
30
31
 $25,000
August 2026
SuMoTuWeThFrSaWeek
 1
$25,000
2
3
4
5
6
7
8
$25,000
9
10
11
12
13
14
15
$25,000
16
17
18
19
20
21
22
$25,000
23
24
25
26
27
28
29
$25,000
30
31
 $17,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$17,000
6
7
8
9
10
11
12
$17,000
13
14
15
16
17
18
19
$15,000
20
21
22
23
24
25
26
$15,000
27
28
29
30
 $15,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Owner reduced rates for August weeks - see calendar for rates

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HERGT

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Property Details
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:
$15,000 - $25,000
June 2026
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
29
30
 $22,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$22,500
5
6
7
8
9
10
11
$22,500
12
13
14
15
16
17
18
$22,500
19
20
21
22
23
24
25
$22,500
26
27
28
29
30
31
 $25,000
August 2026
SuMoTuWeThFrSaWeek
 1
$25,000
2
3
4
5
6
7
8
$25,000
9
10
11
12
13
14
15
$25,000
16
17
18
19
20
21
22
$25,000
23
24
25
26
27
28
29
$25,000
30
31
 $22,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$22,500
6
7
8
9
10
11
12
$20,500
13
14
15
16
17
18
19
$18,500
20
21
22
23
24
25
26
$18,500
27
28
29
30
 $18,500
Clean Fee: 
$850 per week ($650 interim clean)
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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CARDA

(0)Inquire/Share
Property Details
Essence of Chilmark Living, Tucked on High Knoll Providing Expansive Waterviews of the Atlantic, Luxurious Custom Design, Lush Gardens, 5 minute Drive to Lucy Vincent Beach

Experience the essence of Martha's Vineyard with family and friends at this exceptional home nestled on Peaked Hill in Chilmark, offering breathtaking views of the Atlantic. Set on 8 acres...Read more

Location: 
Chilmark
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$18,000 - $25,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$18,000
7
8
9
10
11
12
13
$18,000
14
15
16
17
18
19
20
$18,000
21
22
23
24
25
26
27
$18,000
28
29
30
 $25,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$25,000
5
6
7
8
9
10
11
$25,000
12
13
14
15
16
17
18
$25,000
19
20
21
22
23
24
25
$25,000
26
27
28
29
30
31
 $25,000
August 2026
SuMoTuWeThFrSaWeek
 1
$25,000
2
3
4
5
6
7
8
$25,000
9
10
11
12
13
14
15
$25,000
16
17
18
19
20
21
22
$25,000
23
24
25
26
27
28
29
$25,000
30
31
 $25,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$25,000
6
7
8
9
10
11
12
$18,000
13
14
15
16
17
18
19
$18,000
20
21
22
23
24
25
26
$18,000
27
28
29
30
 $18,000
Clean Fee: 
$850 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:
$4,800 - $13,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,350
7
8
9
10
11
12
13
$7,350
14
15
16
17
18
19
20
$8,000
21
22
23
24
25
26
27
$12,400
28
29
30
 $13,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$13,000
5
6
7
8
9
10
11
$13,000
12
13
14
15
16
17
18
$13,000
19
20
21
22
23
24
25
$13,000
26
27
28
29
30
31
 $13,500
August 2026
SuMoTuWeThFrSaWeek
 1
$13,500
2
3
4
5
6
7
8
$13,500
9
10
11
12
13
14
15
$13,500
16
17
18
19
20
21
22
$13,500
23
24
25
26
27
28
29
$13,000
30
31
 $8,300
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,300
6
7
8
9
10
11
12
$7,650
13
14
15
16
17
18
19
$7,650
20
21
22
23
24
25
26
$7,650
27
28
29
30
 $4,800
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Owner reduced rates for available dates in July & August - see calendar for adjusted rates

 

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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BIALS

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Property Details
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:
$6,500 - $11,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,500
7
8
9
10
11
12
13
$8,500
14
15
16
17
18
19
20
$8,500
21
22
23
24
25
26
27
$8,500
28
29
30
 $10,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,500
5
6
7
8
9
10
11
$10,500
12
13
14
15
16
17
18
$11,000
19
20
21
22
23
24
25
$11,000
26
27
28
29
30
31
 $11,000
August 2026
SuMoTuWeThFrSaWeek
 1
$11,000
2
3
4
5
6
7
8
$11,000
9
10
11
12
13
14
15
$11,000
16
17
18
19
20
21
22
$11,000
23
24
25
26
27
28
29
$11,000
30
31
 $10,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$9,500
13
14
15
16
17
18
19
$9,000
20
21
22
23
24
25
26
$9,000
27
28
29
30
 $9,000
Clean Fee: 
$500
Tax: State & Local: 
11.7
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MEINT

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Property Details
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:
$5,000 - $10,000
June 2026
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
 $10,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,000
5
6
7
8
9
10
11
$10,000
12
13
14
15
16
17
18
$10,000
19
20
21
22
23
24
25
$10,000
26
27
28
29
30
31
 $12,000
August 2026
SuMoTuWeThFrSaWeek
 1
$12,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$12,000
16
17
18
19
20
21
22
$12,000
23
24
25
26
27
28
29
$10,000
30
31
 $7,000
September 2026
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
 $5,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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LITRA

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Property Details
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:
$5,000 - $9,500
June 2026
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
 $5,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$8,500
19
20
21
22
23
24
25
$8,500
26
27
28
29
30
31
 $8,500
August 2026
SuMoTuWeThFrSaWeek
 1
$8,500
2
3
4
5
6
7
8
$9,500
9
10
11
12
13
14
15
$9,500
16
17
18
19
20
21
22
$9,500
23
24
25
26
27
28
29
$9,500
30
31
 $5,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
 $5,000
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7

Ferry Tickets available for week of 8/29-9/5 - please inquire

This home books Fri to Fri in July & August

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PEALY

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Property Details
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:
$3,500 - $6,050
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $5,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,800
5
6
7
8
9
10
11
$5,800
12
13
14
15
16
17
18
$5,800
19
20
21
22
23
24
25
$5,800
26
27
28
29
30
31
 $6,050
August 2026
SuMoTuWeThFrSaWeek
 1
$6,050
2
3
4
5
6
7
8
$6,050
9
10
11
12
13
14
15
$6,050
16
17
18
19
20
21
22
$6,050
23
24
25
26
27
28
29
$6,050
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 $3,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
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WEBSL

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Property Details
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:
$3,520 - $6,030
June 2026
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
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21
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23
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25
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27
28
29
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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LEWID

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Property Details
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:
$4,000 - $6,000
June 2026
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July 2026
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August 2026
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September 2026
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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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LEWDG

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Property Details
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:
$3,000 - $4,000
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$300 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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PERRG

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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:
$3,600 - $4,000
June 2026
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$3,600
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$3,800
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July 2026
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August 2026
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$4,000
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$4,000
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 $4,000
September 2026
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$3,600
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$3,600
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 $3,600
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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SPANM

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Property Details
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:
$3,480 - $3,930
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$300 per week, $200 interim cleaning on multiple week rentals
Tax: State & Local: 
11.7

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