Chilmark Vacation Rentals

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Looking across Chilmark Pond to the Atlantic, Heated pool!

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ENGLJ

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:

Bedrooms:

Baths:

Price Range:

$30,002 - $60,004

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

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:

Bedrooms:

Baths:

Price Range:

$30,002 - $45,003

Clean Fee:

$600 per week

Tax: State & Local:

11.7

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SUDRL

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:

Bedrooms:

Baths:

Price Range:

$15,001 - $30,002

Clean Fee:

$750 per week

Tax: State & Local:

11.7

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CARDA

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:

Bedrooms:

Baths:

Price Range:

$18,004 - $25,004

Clean Fee:

$850 per week

Tax: State & Local:

11.7

Transferrable Ferry Tickets some weeks. Please Inquire for Details (mv)

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HERGT

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:

Bedrooms:

Baths:

Price Range:

$15,001 - $18,501

Clean Fee:

$850 per week

Tax: State & Local:

11.7

Transferrable ferry ticket available 8/23-8/30. Please inquire for details! (mv)

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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Contemporary Home, Pool and Yard Area, Deck Overlooks Private yard and Pool

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BERNC

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:

Bedrooms:

Baths:

Price Range:

$4,802 - $12,005

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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BIALS

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:

Bedrooms:

Price Range:

$7,504 - $10,500

Clean Fee:

$500

Tax: State & Local:

11.7

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LITRA

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:

Bedrooms:

Baths:

Price Range:

$5,005 - $9,506

Clean Fee:

$475 per week

Tax: State & Local:

11.7

Ferry Tickets available for weeks 7/18-7/25, 8/1-8/8, 8/8-8/15, 8/22-8/29, 8/29-9/5 - please inquire

This home books Fri to Fri in July & August

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WEBSL

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:

Bedrooms:

Baths:

Price Range:

$3,521 - $6,027

Clean Fee:

$375 per week

Tax: State & Local:

11.7

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LEWID

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:

Bedrooms:

Baths:

Price Range:

$3,997 - $6,006

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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MEINT

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:

Bedrooms:

Baths:

Price Range:

$4,998 - $4,998

Clean Fee:

$450 per week

Tax: State & Local:

11.7

Ferry Tickets available for weeks 8/10 - 8/17, 8/24 -8/31 - please inquire

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LEWDG

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:

Bedrooms:

Baths:

Price Range:

$3,003 - $4,004

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

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:

Bedrooms:

Baths:

Price Range:

$3,605 - $4,004

Clean Fee:

$450 per week

Tax: State & Local:

11.7

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SPANM

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:

Bedrooms:

Baths:

Price Range:

$3,374 - $3,927

Clean Fee:

$300 per week, $200 interim cleaning on multiple week rentals

Tax: State & Local:

11.7

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WATTL