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$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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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: 4.53% last updated on Jul 12, 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: 4.53% last updated on Jul 12, 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 $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.

{$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: 4.53% last updated on Jul 12, 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$10,965 to $26,520

Rental ID 116998

  • RTR Vacation Rental
  • Lease $10,965 to $26,520
  • 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.

{$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: 4.53% last updated on Jul 12, 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$4,000 to $12,000

Rental ID 134575

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

This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach! The house lies between West Tisbury (Alley’s General Store, 7A Foods, Farmer’s Market, Artisan’s Market, galleries, etc.) and Chilmark (Chilmark Store, Chilmark Tavern, Chilmark Community Center, etc.). It is also a short ride to Menemsha Village (fishing, fish markets, galleries, restaurants, and sunsets on the beach). This 1713 Mayhew farmhouse underwent a complete gut-renovation in 2017 and was reborn to honor its past while embracing today’s contemporary lifestyle. The house is fully air- conditioned and has Wi-Fi, high speed Internet and cable TV. A beautiful three-season porch was added to the back of the house. It is a relaxing place to sit, read, play a game, watch TV, or simply observe what is going on outside. The porch leads to a bluestone patio with a teak dining table with seating for 8 under a market umbrella along with a number of chairs to relax in and a gas grill. Adjacent to the patio is a large private outdoor shower. The house is surrounded by an expansive lawn bordered by 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 has a farmer’s table that seats up to 10 along with an additional sitting area by the fireplace. The library/media room is a cozy place to sit and talk, read by the fireplace, or binge watch that show you just never got to last year on a large flat screen TV. The final room downstairs is the first, of two, en suite master bedrooms (queen bed). It has a fireplace, flat screen TV, and a marble and tile bathroom. A French door leads from this bedroom to the bluestone patio. The central hallway contains a half bath and two stairways that lead to the second floor where you will find four additional bedrooms, (two queens, one twin and an en suite king), a full laundry and a large bathroom with an oversized tub/shower. The 2nd floor master bedroom (king bed) has a flat screen TV, an attached walk-in closet and en suite marble and tile bath. High quality linens and towels are provided throughout the house. 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 a premier private South Shore ocean beach adjacent to Chilmark Pond so that both can be enjoyed. Tenants can bring kayaks to the pond to explore this beautiful, unspoiled environment. Tenants also have access to Chilmark town beaches—Lucy Vincent and Squibnocket. Beach chairs, towels, umbrellas and coolers are all provided.

{$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: 4.53% last updated on Jul 12, 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$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.

{$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: 4.53% last updated on Jul 12, 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$7,000 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.

{$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: 4.53% last updated on Jul 12, 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: 4.53% last updated on Jul 12, 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$4,500 to $8,000

Rental ID 120745

  • RTR Vacation Rental
  • Lease $4,500 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: 4.53% last updated on Jul 12, 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 $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.

{$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: 4.53% last updated on Jul 12, 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$10,000 to $20,000

Rental ID 116953

  • RTR Vacation Rental
  • Lease $10,000 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!

{$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: 4.53% last updated on Jul 12, 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$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.

{$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: 4.53% last updated on Jul 12, 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