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. You may also be interested in viewing all vacation rentals on the Vineyard.

Chilmark real estate subareas:

Chilmark Vacation Rentals

Questions? Call Coldwell Banker Landmarks Real Estate: 508-693-6866

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Chilmark, MA

Rental Price$10,000 to $15,000

Rental ID 116754

  • RTR Vacation Rental
  • Lease $10,000 to $15,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 3

Wonderful four bedroom home directly on Quitsa Pond with private deep water dock. One bedroom guest cottage included in rental.

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Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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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Chilmark, MA

Rental Price$3,500 to $9,000

Rental ID 116734

  • RTR Vacation Rental
  • Lease $3,500 to $9,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 2

Spectacular views overlooking Squibnocket Pond and Atlantic Ocean. Contemporary home with two spacious living rooms. Walk to Squibnocket beach. Private access to Squibnocket pond, canoe provided. Key is also available for access to private Zach s Cliff Beach, maximum two cars.

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$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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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Chilmark, MA

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: 3.47% last updated on Feb 13, 2020
* 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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Chilmark, MA

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: 3.47% last updated on Feb 13, 2020
* 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

Chilmark, MA

Rental Price$6,500 to $10,000

Rental ID 116399

  • RTR Vacation Rental
  • Lease $6,500 to $10,000
  • 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

Chilmark, MA

Rental Price$6,000 to $13,000

Rental ID 116377

  • RTR Vacation Rental
  • Lease $6,000 to $13,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

Spectacular retreat overlooking sweeping views of Menemsha, Elizabeth Islands, Gay Head Lighthouse and Aquinnah. Wonderfully furnished interior with special features and design throughout. Beautiful stone fireplace, open living area, fully equipped kitchen, perfect for entertaining. Master bedroom offers incredible views with its own private balcony. Relax and enjoy sunsets out on the field stone patio. An amazing summer hideaway.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

Chilmark, MA

Rental Price$3,500 to $6,500

Rental ID 114865

  • RTR Vacation Rental
  • Lease $3,500 to $6,500
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 4

Spacious, contemporary Cape-style home with a wrap around deck tucked into a wooded hilllside on 3.8 acres. Distant waterviews of Cape Higon and Vineyard Sound. The overall design and layout with the 4 bedrooms and 2 lofts allows space for extended family get-togethers and special occasions.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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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Chilmark, MA

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: 3.47% last updated on Feb 13, 2020
* 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

Chilmark, MA

Rental Price$2,500 to $8,000

Rental ID 113585

  • RTR Vacation Rental
  • Lease $2,500 to $8,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 3

Charming, remodeled in 2000, this is a seaside cottage overlooking Menemsha Harbor and beach. Bright and open interior with upscale details, the house is very comfortable. Master suite upstairs with deck and views of harbor, beach and sunsets. Backyard is private with outdoor deck and screened in porch. Guest cottage on the property with one bedroom and bath. Outdoor shower attached to guest house.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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

Chilmark, MA

Rental Price$4,000 to $13,000

Rental ID 116976

  • RTR Vacation Rental
  • Lease $4,000 to $13,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

This mission style home is full of charm and warmth. Complete with two master bedrooms, both with water views and perched on a hill overlooking sweeping views of the Atlantic and Squibnocket Pond add to the magic of this special property.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.47% last updated on Feb 13, 2020
* 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