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:

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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.

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Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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$2,500 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!

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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.

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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$12,000 to $22,000

Rental ID 116303

  • RTR Vacation Rental
  • Lease $12,000 to $22,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 2

Beautiful converted barn located in exclusive Squibnocket Farm. Access to one of the Vineyards most pristine and private ocean beaches. This home has the original exposed beams and floor to ceiling windows offering spectacular views of the surrounding meadows, ocean, pond and gardens. Balconies and lofts overlook the large open living area below. Tastefully decorated furnishings and artwork with modern amenities throughout. A rare opportunity to experience this special area of the island.

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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$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.

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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$2,500 to $7,500

Rental ID 113585

  • RTR Vacation Rental
  • Lease $2,500 to $7,500
  • 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.

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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 $8,500

Rental ID 131781

  • RTR Vacation Rental
  • Lease $7,500 to $8,500
  • Village Chilmark
  • Bedrooms 3
  • Bathrooms 2

The house is in an idyllic location on Upper Chilmark Pond. It has direct pond access and the ocean is directly across the pond. Lucy Vincent Beach is a short walk West along the shore. The property is 3 miles from Alley s and 7A in West Tisbury and 1.5 miles from the Chilmark store.

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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

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

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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

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.

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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

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.

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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

Rental Price$15,000 to $15,000

Rental ID 116957

  • RTR Vacation Rental
  • Lease $15,000 to $15,000
  • Village Chilmark
  • Bedrooms 6
  • Bathrooms 4

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.

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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

Rental Price$7,000 to $7,000

Rental ID 116499

  • RTR Vacation Rental
  • Lease $7,000 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.

{$office->Name}

Coldwell Banker Landmarks Real Estate
15 Church Street
Vineyard Haven MA, 02568
Office: 508-693-6866

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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