Chilmark Vacation Rentals

Discover our latest vacation rentals in the Martha's Vineyard town of Chilmark. Look through a variety of listings including beautiful oceanfront homes, luxury estates, cottages, and more! Save your favorites when you register with us, and we can send you email updates when similar properties are posted. If you already have an account with us, log in here. Please feel free to contact us with any questions, for more information, or to schedule a showing for any property below!

Rental Price$6,000 to 10,000

Rental ID 134575

  • RTR Vacation Rental
  • Lease $6,000 to $10,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

The Zaccheus Mayhew House (1713) has been described as "the largest and most stately of the early houses on the South Road". It recently underwent a complete gut renovation. It is now a fully functional contemporary home inside a Colonial post and beam frame. While it is mostly new, it maintains a lot of its original Colonial period character (exposed beams, wide board floors, wainscoting, etc.). The first floor has a large center hall with two staircases. Also on the first floor are a library/media room with a large flat screen TV and gas fireplace; a dining room with a large farmer s table, gas fireplace and two comfortable upholstered chairs that invite you to sit and read for a spell, as well as an en-suite queen sized bedroom with a gas fireplace and TV. There is also a fully equipped cook s kitchen with an island that includes stool seating, high-end stainless steel appliances as well as quartz and butcher block countertops and a small TV; a half bathroom and a three-season cathedral-ceilinged porch that leads to a large bluestone patio with a gas grill as well as dining, seating and reclining options. Adjacent to the patio is a large enclosed outdoor shower. The house is surrounded by a beautiful, large, private backyard with specimen trees all defined by traditional Chilmark stonewalls. The second floor, in addition to a large king-six=zed master bedroom suite with TV, includes three additional bedrooms - two queen-sized and one double twin bedrooms; a full soaker tub/shower combination bathroom; and an adjacent full-sized laundry. This lovely, comfortable home has high-end finishes and is fully air-conditioned. In addition, tenants have access to the highly sought after Hancock Beach - a private association beach located 1 mile from the residence via private roadway. Tenants can also transport their own kayaks to Hancock Beach where they can launch them and fully explore the calm waters of Chilmark Pond-one of the island s most beautiful natural habitats

{$agent->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: 4.03% last updated on Jul 13, 2017
* 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$25,000 to 30,000

Rental ID 133977

  • RTR Vacation Rental
  • Lease $25,000 to $30,000
  • 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.

{$agent->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: 4.03% last updated on Jul 13, 2017
* 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 9,000

Rental ID 126309

  • RTR Vacation Rental
  • Lease $7,000 to $9,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 2

This contemporary home commands one of Martha s Vineyard s most spectacular 180 degree views overlooking the Elizabeth Islands and Vineyard Sound. You will experience breathtaking sunsets as you dine in or out. Situated high on one of Chilmark’s hills, this home is bright and airy with colorful appointments and artwork to be enjoyed. Open kitchen, living, dining and master bedroom is on the upper level with a wrap-around deck. On the first floor you will find family/TV room and remaining four bedrooms. This house offers a great up-island Vineyard experience with the charm of a nearby fishing village, access to Lucy Vincent Beach, hiking trails and much more.

{$agent->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: 4.03% last updated on Jul 13, 2017
* 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

{$agent->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: 4.03% last updated on Jul 13, 2017
* 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$5,000 to 6,000

Rental ID 120760

  • RTR Vacation Rental
  • Lease $5,000 to $6,000
  • 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.

{$agent->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: 4.03% last updated on Jul 13, 2017
* 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.

{$agent->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: 4.03% last updated on Jul 13, 2017
* 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$7,500 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.

{$agent->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: 4.03% last updated on Jul 13, 2017
* 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$14,000 to 20,000

Rental ID 116953

  • RTR Vacation Rental
  • Lease $14,000 to $20,000
  • 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!

{$agent->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: 4.03% last updated on Jul 13, 2017
* 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$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.

{$agent->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: 4.03% last updated on Jul 13, 2017
* 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$1,050 to 3,250

Rental ID 116588

  • RTR Vacation Rental
  • Lease $1,050 to $3,250
  • 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.

{$agent->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: 4.03% last updated on Jul 13, 2017
* 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