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

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Chilmark, MA

Rental Price$3,000 to $5,500

Rental ID 116920

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

Beautifully furnished and decorated home with all the amenities. Bright, airy two story interior, lovely views over Stonewall Pond to the barrier beach beyond, great sunsets via roof deck. Two story fireplace, recently renovated kitchen with all new appliances and granite tile counters. Complete privacy, cedar filled property borders Stonewall Pond - excellent for swimming! A walk to Town landing and Stonewall Beach.

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Federal 30-year interest rate: 3.49% last updated on Feb 20, 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 $11,700

Rental ID 126257

  • RTR Vacation Rental
  • Lease $4,000 to $11,700
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 3

This mid - century modern four bedroom with a 4 foot wading pool is not to be missed! Master offers air conditioning and private bath. Located just past Able s Hill perched on hill abutting conservation land you really feel away from it all.

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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$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.

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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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$22,500 to $22,500

Rental ID 130842

  • RTR Vacation Rental
  • Lease $22,500 to $22,500
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 4

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$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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$5,000 to $6,000

Rental ID 125237

  • RTR Vacation Rental
  • Lease $5,000 to $6,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 2

Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four bedroom, 2 bath home has an expansive rear deck that offers panoramic water views. The main level offers an open kitchen and large living room complete with fireplace. An entire wall is floor to ceiling glass with French doors opening onto a large deck. All of the rooms on this floor offer stunning views, including the Master bedroom. The first level features a large family room and three ample sized bedrooms.

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%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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$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: 3.49% last updated on Feb 20, 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$2,000 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: 3.49% last updated on Feb 20, 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$6,500 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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$
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$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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$2,500 to $6,000

Rental ID 119742

  • RTR Vacation Rental
  • Lease $2,500 to $6,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 2

Located on the North side of Chilmark, this contemporary getaway offers a wide open living space with vaulted ceilings, stylish furnishings, a spacious deck and a stunning widow’s watch with water views. Completely renovated in 2012, this home feels like new and features a brand new kitchen with top of the line appliances, luxury showers with multiple fixtures and central air conditioning. Set on over two acres of land, the property boasts multiple gardens, a private outdoor shower and a fire pit. There are several Land Bank properties within walking distance, including the historic hiking trails at Waskosim’s Rock Reservation. For beach goers, you get access to gorgeous Lucy Vincent beach and are a bike ride away from the beach at Great Rock Bight, a well-kept secret among locals. The Chilmark Flea is just around the corner for those looking for an authentic up island experience. Perfect for families, this is a great venue to recharge and reconnect amidst some of the island’s most beautiful scenery.

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$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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$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.

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$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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$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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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$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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.49% last updated on Feb 20, 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