Chilmark Rentals

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241 Houses

Chilmark Farmhouse with access to Hancock Beach

Chilmark house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$714

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

Chilmark house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$900

Gracious and Spacious Chilmark Home with a Pool

Chilmark house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$686

CHARMING COUNTRY HOME IN CHILMARK

Chilmark house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$500

Great rentals within 20 miles that match your search

Walk to Private Beach

Falmouth studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$148

Salt Water Front South of Rt. 28 with Private Dock and Amazing Views!

Teaticket house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$658

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Price per night from

$3,831

Walk to the Beach! NEW Hot Tub! Pets welcome!

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$387

Renovated Cottage near center and beaches

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$801

Coastal Contemporary in Katama / South Beach / Edgartown / Bike Paths /

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$601

New Construction beach retreat- 1/3 of a mile from Old Silver Beach

Silver Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$1,024

Vineyard Charming Retreat near beaches and center

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$401

Spacious Beach House 6 Min Walk to Beach!

Waquoit house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$269

Style & Comfort at Modern Waterfront Home!

Waquoit house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$291

Deluxe suite at the oceanfront Surfside Resort

Falmouth hotel apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$458

#CozyBluffs 1 BR House in Historic Oak Bluffs - walk to town and ferry

Oak Bluffs house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$801

Captain's Quarters charming oceanfront resort with swimming pool

Falmouth hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$458

Captain's Quarters - charming oceanfront resort with swimming pool

Falmouth hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$458

West Wing of Captain Morse House Waterfront, Town & Beach - Pets OK, - 5 stars

Oak Bluffs house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$626

East Wing of Captain's Mansion - Luxury, Waterfront, Town, & Beaches - 5 stars

Oak Bluffs house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$734

Quiet, Pet Friendly, Close to Edgartown and Oak Bluffs Beaches - FIVE STARS

Edgartown guest house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$241

Sea Glenn Flowers Private home new to market

Vineyard Haven house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$481

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Price per night from

$241

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$1,963

Seaside cottage

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$492

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Price per night from

$781

3 bedroom 2 bath Fully remodeled home

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$315

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$829

Heated Pool, AC, WiFi, Sleeps 18, 2 mi to beach!

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

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Price per night from

$6,870

Luxurious Captains Mansion - Waterfront, Town, & Beaches - 5 stars

Edgartown house

  • 12 bedrooms
  • 7 bathrooms
  • sleeps 26

“great trip!” Definately would do it again! Loved the house and the area. Marthas Vineyard is a very special place!

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Price per night from

$866

GREAT VACATION HOUSE-GREAT LOCATION TO SOUTH BEACH

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$344

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

66 Central Ave

Falmouth farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$210

Waterfront Resort in Falmouth - 5/31/24 - 6/7/24

Falmouth apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$172

Clean, comfortable ranch with lots of amenities

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$544

Katama House "CLOSE TO THE BEACH"

Acushnet house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$311

Great Family Home, Close to South Beach, And Town

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

Great Martha's Vineyard Island Cottage!

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

Viewing 38 of 241
rentals in Chilmark

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