Chilmark Rentals

Discover the latest rentals available in Martha's Vineyard's seaside village of Chilmark. When you register with us you can save your favorite searches, and receive updates when similar are posted. If you already have an account with us, log in here!

Learn more about Chilmark.

Search through a variety of beautiful listings, and feel free to contact us if you have any questions or would like to schedule a tour.

Rental Price$2,500 to $8,000

Rental ID 113585

  • RTR Vacation Rental
  • Lease $2,500 to $8,000
  • 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.

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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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$2,000 to $5,000

Rental ID 116972

  • RTR Vacation Rental
  • Lease $2,000 to $5,000
  • 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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$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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 $18,000

Rental ID 116303

  • RTR Vacation Rental
  • Lease $12,000 to $18,000
  • 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: 4.63% last updated on Dec 13, 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 $4,000

Rental ID 116331

  • RTR Vacation Rental
  • Lease $2,500 to $4,000
  • Village Chilmark
  • Bedrooms 2
  • Bathrooms 1

What could be a more elegant, peaceful and romantic hideaway for a week than the Pond House? It sits at the conjunction of ocean and land, pond and meadow, with a view beyond dazzling outside and a warm fire in the fireplace inside. Gourmet kitchen. Antique and comfortable furniture. Quality bedding. Toasty. Snug. Sweet. Free Wifi. Hundreds of books. Outside, walks to be taken. Inside, dreams to be dreamed. Kayaks are always available if the weather encourages such bold adventure. Truly, the Pond House is a remarkable cottage, beautiful and well maintained, completely fitted-out to the highest standard. Main house is next door.

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%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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$3,000 to $5,000

Rental ID 116330

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

Sunrise from the ocean, sunset over Stonewall Pond and view towards Squibnocket Beach. Old Vineyard look and feel, an elegant and comfortable beach house with landscaped gardens. Recently built 500 sq ft addition includes ground floor MBR suite offering full amenities. On-site recreation includes kayaks, canoe, sail boat, clam rakes and buckets, as well as mountain bikes, road bikes, walking sticks and walking guides. For a more detailed list of services provided or arranged please contact your rental agent.

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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.

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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 $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.

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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 $6,700

Rental ID 116921

  • RTR Vacation Rental
  • Lease $3,500 to $6,700
  • Village Chilmark
  • Bedrooms 3
  • Bathrooms 2

Beautiful Chilmark setting, located on Stonewall Pond with spectacular waterviews! The east offers views of Stonewall Pond to the Atlantic ocean. The west offers views of Quitsa Pond to Menemsha Pond. Great outdoor deck perfect for relaxing and/or outdoor entertaining. Large sweeping lawn and mature landscaping provide a nice up-island feel. Private mooring available. Access to Stonewall Beach, just a short walk away.

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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$3,000 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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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$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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 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