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$2,000 to $5,500

Rental ID 142111

  • RTR Vacation Rental
  • Lease $2,000 to $5,500
  • Village Chilmark
  • Bedrooms 3
  • Bathrooms 1

Charming cottage with water view just steps into Menemsha. Great outdoor deck, new kitchen - everything recently updated. Wonderful antiques for decoration and top quality furnishings throughout.

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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$1,250 to $2,500

Rental ID 116552

  • RTR Vacation Rental
  • Lease $1,250 to $2,500
  • Village Chilmark
  • Bedrooms 2
  • Bathrooms 1

Nice two bedroom cottage located in the heart of Menemsha. Watch the beautiful sunsets from the deck while dining. Five minute walk to beach, fish market or quaint shops in this fishing village.

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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$8,000 to $18,000

Rental ID 116302

  • RTR Vacation Rental
  • Lease $8,000 to $18,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 3

Squibnocket Farm is comprised of over 325 acres of beautiful rolling land nestled between Squibnocket Pond and the Atlantic Ocean. A very exclusive island location with only a few homes throughout the farm. Private access to a world-class beach and Squibnocket Pond - a rare combination of rural habitats. The home includes fine furnishings throughout with a fabulous kitchen and living area.

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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$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.

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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$1,250 to $3,500

Rental ID 116588

  • RTR Vacation Rental
  • Lease $1,250 to $3,500
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 2

Spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. House is fully equipped, open living area with cathedral ceilings, wood floors, operable skylights, large outdoor deck and separate family room with sleeper sofa. Private setting with access to Chilmark beaches. The home is perfect for couples, families with children or a couple of families who want to share their vacation. Cleaning and trash collection are included.

$
$
%
$/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$25,000 to $25,000

Rental ID 133977

  • RTR Vacation Rental
  • Lease $25,000 to $25,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

The house itself is spacious with elegant details, state of the art systems, and an attractive floor plan. Craftsmanship quality in this 5,400 square foot home is everywhere, from the kitchen, with its granite counters, center island with copper counter, custom cabinetry, and tile floors & backsplash. To the living areas and bedrooms, that include heart pine flooring, high-ceilings with exposed wood beams, wainscoting and moldings. And, the bathrooms, with their high-end fixtures, tile flooring and custom elements. The kitchen includes a Sub-Zero refrigerator, eight-burner, gas, Viking, stovetop, and two Bosch dishwashers. Heating/AC system includes a Viessmann boiler, forced hot air heat and air conditioning, and radiant heat in the lower level. Floor plan includes a number of bonus areas, table tennis room, media/TV room, wine cellar with brick floor and cedar paneling; two master suites, and an open main level that centers on the living room, which includes cathedral ceilings, fieldstone fireplace, and egress to exterior decking. Many rooms with water views. This beautiful home features all of the finest amenities as well as a heated pool for outdoor entertaining and enjoyment and just recently put tennis court.

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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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Rental ID 116953

  • RTR Vacation Rental
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 4

This is a peaceful four bedroom Cape located directly on Chilmark Pond with a highly desirable Hancock Beach Association key. Tastefully decorated with all amenities. the first floor includes an open concept living room, dining cook s kitchen with an adjacent pantry laundry room. there two en suite bedrooms and a three season porch. All rooms overlook Chilmark Pond. Upstairs includes two en suite bedrooms and a tv room that leads a second floor deck with views of Chilmark Pond. This home offers all ingredients necessary to create a wonderful and relaxing up island vacation escape. It is conveniently located between West Tisbury and Chilmark village centers. Kick back and enjoy the best that Chilmark has to offer!

$
$
%
$/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$10,965 to $26,500

Rental ID 116998

  • RTR Vacation Rental
  • Lease $10,965 to $26,500
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 5

Located in one of the most exclusive associations on the Vineyard, this five bedrooms home offers some of the most stunning water views the island has to offer. This home includes spacious decks, vaulted ceilings, and all the amenities one expects in a premier property. Tenants have access to both the association and homeowners beaches.

$
$
%
$/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 $9,750

Rental ID 116752

  • RTR Vacation Rental
  • Lease $7,500 to $9,750
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 4

Relax and enjoy sweeping views of the South Shore from the upper deck balcony. Sprawling interior design provides an open and comfortable space, ideal for family living. A fully loaded kitchen with top of the line appliances, perfect for entertaining. Unwind in the screened-in porch which overlooks an amazing yard. Ideally located near desirable Lucy Vincent beach.

$
$
%
$/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$4,000 to $12,000

Rental ID 134575

  • RTR Vacation Rental
  • Lease $4,000 to $12,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

This fully renovated 5-bedroom, 3½ bath, farmhouse is set well back behind Chilmark stonewalls and comes with a key to the private South Shore Hancock Beach! The house lies conveniently between West Tisbury and Chilmark town centers. This Mayhew farmhouse underwent a complete gut-renovation in 2017 and was reborn to embrace today’s contemporary lifestyle. The house is fully air-conditioned, has Wi-Fi, high speed Internet and cable TV. A beautiful enclosed porch was added to the back of the house. The porch leads to a lovely, private bluestone patio with a teak dining table, lounge chairs and gas grill. Adjacent to the patio is a large outdoor shower. Beyond the patio is a very private expansive back yard bordered by Chilmark stonewalls. The house is remarkably open on the first floor. The porch leads into a fully equipped cook’s kitchen with high-end appliances, quartz countertops and an island with seating. The dining room with fireplace seats up to ten comfortably. The library/media room is a peaceful place to gather, read, or watch TV by the fireplace. Also on the first floor is an en-suite queen-sized master bedroom with a third fireplace and a French door that leads to the outside patio. The central hallway, with half bath, has double stairways that lead to the second floor. Here one finds four additional bedrooms, a full laundry and a large bathroom with an oversized tub/shower. The king-sized 2nd floor master bedroom has a flat screen TV, and an attached walk-in closet and en-suite master bath. The real bonus of this house is its key to Hancock Beach—located approximately 1.5 miles from the house down a private road. Hancock Beach is adjacent to Chilmark Pond so that both can be enjoyed. Tenants also have access to Chilmark town beaches –Lucy Vincent and Squibnocket.

$
$
%
$/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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Rental ID 114884

  • RTR Vacation Rental
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 4
  • Half Baths 1

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: 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$2,500 to $4,400

Rental ID 116925

  • RTR Vacation Rental
  • Lease $2,500 to $4,400
  • Village Chilmark
  • Bedrooms 1
  • Bathrooms 1

Adorable, private boathouse at the edge of Stonewall Pond. Wrap around deck provides gorgeous views (as well as sound effects) of the pond and the barrier beach beyond, great for swimming! Perfect for a small family or a romantic getaway. An idyllic 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