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Chilmark

Chilmark Holiday Rentals

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B&Bs / Inns (6)

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Holiday Rentals (33)

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[ Recommended ] [ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 2
Min stay:1
The Oak Meadow House is situated on 3.4 acres of land off North Road in North Tabor Farm-formerly the James Cagney Estate. It is a two-level contemporary, ...
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    £739 - £2,218
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Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 7
Bathrooms: 2
Min stay:1
An adorable seaside cottage sits atop a shallow bluff on the South Shore of rural Chilmark and boasts a grand and glorious oceanview. Please note that "Acts ...
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    £3,696 - £9,241
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Management: Verified owner
Property: Holiday Rental House
Bedrooms: 5, sleeps 10
Bathrooms: 4
Min stay:5
This five-bedroom/four-bath home is located in Chilmark. It features water views of the Atlantic Ocean, a very private setting on over five acres, and ...
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    £2,772
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Management: Verified owner
Property: Cabin Holiday Rental
Bedrooms: 3, sleeps 6
Bathrooms: 1
Min stay:5
This modern two-bedroom/one-bath home with a large sleeping loft sleeps six-plus people. It's located 'up island' on four acres in a very private setting, ...
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    £1,540
Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 3
Tastefully furnished and decorated with antique accents and art. This lovely, upscale, Chilmark summer home sits off South Road and has plenty of light and ...
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    £1,047 - £2,156
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Management: Professional
Property: Holiday Rental House
Bedrooms: 6, sleeps 10
Bathrooms: 5
Min stay:1
Spacious, 10 room, architectual award-winning design home perched atop a hill w/panoramic view of Vineyard Sound and the Elizabeth Islands. The large deck has ...
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    £3,696 - £6,161
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Management: Professional
Property: Holiday Rental House
Bedrooms: 6, sleeps 12
Bathrooms: 4
Historic 18th century New England home in a private landscaped setting on two and 1/2 acres with a waterview over Vineyard Sound and the Elizabeth Islands; a ...
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    £2,772 - £7,393
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Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 3
Min stay:2
Front of house and patio Policy: Pets not allowed, Not handicap accessible Minimum Stay: 2 weeks
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    £10,165
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Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 3
Chilmark pondfront property with beautiful south shore views of pond, barrier beach and the Atlantic. Abel's Hill Beach and tennis rights. Walk to pond and ...
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    £1,848 - £7,393
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Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 2
Classic Eliot Noyes (architect) contemporary with spectacular views Lucy Vincent beach east towards West Tisbury. There is a great room (with dining, and ...
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    £2,464 - £4,312
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Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 3
Unique combination of 1940's camp-style home and new (2007) two-story addition. Beautiful Ocean views from all floors, two decks, two living rooms and ...
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    £2,772 - £4,620
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Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 2
This spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. The master bedroom and bath are ...
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    £616 - £1,817
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Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 4
Winter view! Policy: Pets not allowed, Not handicap accessible
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    £1,540 - £3,388
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Management: Professional
Property: Holiday Rental House
Bedrooms: 4, sleeps 8
Bathrooms: 3
Min stay:1
C-H-A-R-M-I-N-G is the only word to describe this privately set little contemporary with a big heart, tucked right into the woods in Spring Point. Lovely view ...
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    £1,232 - £2,932
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Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 4
Bathrooms: 1
The Pond House, located on Stonewall beach in Chilmark, is a charming cottage is situated on the edge of the rolling lawns of the main house. The beauty and ...
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    £2,464 - £4,312
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Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns