Chilmark Rentals

CHILMARK is the island’s most bucolic town, featuring rolling pastures and the scenic byways of North, Middle and South Roads. Miles of stone fences date back to the English settlements of the 1700s. Today, they define sheep and horse farms as well as the secluded homesteads of “settlers” of the present day. Chilmark’s south shore beaches are considered some of Martha’s Vineyard’s finest. The town’s quaint fishing village of Menemsha is popular in summer with seafood picnickers and sunset watchers. 

Learn more about Chilmark.

Chilmark real estate subareas:

Please contact Coldwell Banker Landmarks Real Estate online or call 508-693-6866 with any questions about Martha’s Vineyard vacation rentals.

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Rental Price$2,500 to $2,800

Rental ID 116554

  • RTR Vacation Rental
  • Lease $2,500 to $2,800
  • Village Chilmark
  • Bedrooms 3
  • Bathrooms 2

This charming newly remodeled three bedroom, two bath Cape has a spacious master bedroom suite, cozy sun room and updated kitchen. Spend your Chilmark vacation here and enjoy rights to desirable Lucy Vincent and Squibnocket beach. A memorable up-island retreat awaits you!

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Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$6,500 to $9,000

Rental ID 116399

  • RTR Vacation Rental
  • Lease $6,500 to $9,000
  • Village Chilmark
  • Bedrooms 6
  • Bathrooms 4

Wonderful, Vineyard oversized Cape with expansive views of picturesque farmland (Keith Farm) and Atlantic Ocean. Separate main house and guest house allow for comfortable space between guests and families. Extremely charming home with all necessary amenities; beautifully renovated kitchen. Very close to Chilmark center and a quick drive, walk or hike to Lucy Vincent beach. Excellent location.

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$2,000 to $4,500

Rental ID 120760

  • RTR Vacation Rental
  • Lease $2,000 to $4,500
  • Village Chilmark
  • Bedrooms 2
  • Bathrooms 1

Chilmark family retreat. Overlooking the expansive meadows of Grey Barn s 62 acres of protected farmland. 2 bedrooms with an additional sleeping loft. Exclusive up-island beach access to Squibnocket and Lucy Vincent.

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$5,500 to $9,500

Rental ID 116766

  • RTR Vacation Rental
  • Lease $5,500 to $9,500
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 3

Expansive distant waterviews overlooking Vineyard Sound on three and a half acre property. Located in desirable Spring Point, this 40 home association is accessed by a private, well maintained dirt roads with 40 acres of common land consisting of nature trails and a private beach on the Sound. This property is nicely landscaped with two substantial gardens. A private mooring at Quitsa Pond along with Association Tennis.

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$4,000 to $9,400

Rental ID 116670

  • RTR Vacation Rental
  • Lease $4,000 to $9,400
  • Village Chilmark
  • Bedrooms 3
  • Bathrooms 2

Classic Vineyard Cape with exquisite rolling landscape and old stone walls. Views of Menemsha Pond and Vineyard Sound. Private white sandy beach. Peaceful up-island vacation retreat. Homeowner will include one bedroom-2 bath guesthouse for an additional fee. Please contact an agent for more details.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$6,000 to $7,000

Rental ID 116499

  • RTR Vacation Rental
  • Lease $6,000 to $7,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 1

Watch the sun set from your private, romantic waterfront cottage with unparalleled views of Menemsha Pond, wetlands, ocean, Elizabeth Islands and Gay Head. Key to a private Gay Head Beach is included with rental.

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$10,000 to $10,000

Rental ID 113602

  • RTR Vacation Rental
  • Lease $10,000 to $10,000
  • Village Chilmark
  • Bedrooms 3
  • Bathrooms 3

Beautifully renovated and restored antique Cape situated in Chilmark on two ponds. Three bedroom home plus loft area. Tastefullly furnished throughout with full modern amenities. Living room, dining room as well as an eat-in kitchen. Includes a game room with pool table and sitting area for relaxing and enjoying family time together. The perfect up-island retreat with access to Squibnocket and Lucy Vincent beach.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$6,500 to $8,000

Rental ID 120745

  • RTR Vacation Rental
  • Lease $6,500 to $8,000
  • Village Chilmark
  • Bedrooms 3
  • Bathrooms 3

Chilmark family compound. Overlooking the expansive meadows of Grey Barn s 62 acres of protected farmland. The Main house offers 3 bedrooms and a separate lovely bunk house, with kitchenette. The wraparound porch is complete with a hammock to relax on and a ping pong table for family fun.

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$8,000 to $10,000

Rental ID 114884

  • RTR Vacation Rental
  • Lease $8,000 to $10,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 4

Spacious up-island home situated high on hill of desirable Spring Point. Enjoy great sunsets and sweeping waterviews of the Atlantic on the outer decks and patio. Thoughtfully designed for privacy, two master bedrooms on either end of home, two living rooms one up and one down. Large kitchen, vaulted ceilings in great room, plus great space for kids in lower level (tv room). Perfect getaway for a large or extended family vacation.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$22,000 to $25,000

Rental ID 123611

  • RTR Vacation Rental
  • Property Name Chilmark -
  • Lease $22,000 to $25,000
  • Village Chilmark
  • Bedrooms 4

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental ID 116957

  • RTR Vacation Rental
  • Village Chilmark
  • Bedrooms 6
  • Bathrooms 4
  • Half Baths 2

Exceptional, private home set high on a hill with views of Menemsha Pond and Atlantic Ocean. Great outdoor space for entertaining and/or relaxing on the patio as well as deck areas. Beautifully landscaped setting with gardens and stonework throughout yard. Post and beam, tastefully furnished with hardwood floors throughout. First floor offers a large living room, open dining area with gourmet kitchen. Second floor views of South Shore from master bedroom. Walking path to Squibnocket beach, the perfect up-island retreat.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rental Price$7,500 to $11,000

Rental ID 119397

  • RTR Vacation Rental
  • Property Name Quansoo area retreat
  • Lease $7,500 to $11,000
  • Village Chilmark
  • Bedrooms 4

Stunning Quansoo/Great Pond setting. Lots of room to roam and explore at this waterfront property, which includes access to Quansoo beach, a private dock for launching your kayaks from, and a relaxing setting from which to take in the beautiful views this property has to offer. Air conditioned throughout, screened in porch, and many other amenities – this home offers a perfect vacation stay for any family.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details