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! You may also be interested in browsing all of our vacation rentals.

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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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Federal 30-year interest rate: 3.18% last updated on Jun 4, 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.

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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: 3.18% last updated on Jun 4, 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 TourAsk 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.

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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: 3.18% last updated on Jun 4, 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$10,000 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!

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 TourAsk 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.

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 TourAsk A QuestionMore Details

Chilmark, MA

Rental Price$6,000 to $13,000

Rental ID 116377

  • RTR Vacation Rental
  • Lease $6,000 to $13,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

Spectacular retreat overlooking sweeping views of Menemsha, Elizabeth Islands, Gay Head Lighthouse and Aquinnah. Wonderfully furnished interior with special features and design throughout. Beautiful stone fireplace, open living area, fully equipped kitchen, perfect for entertaining. Master bedroom offers incredible views with its own private balcony. Relax and enjoy sunsets out on the field stone patio. An amazing summer hideaway.

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 TourAsk A QuestionMore Details

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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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 TourAsk A QuestionMore Details

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 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 TourAsk A QuestionMore Details