Chilmark: Vacation Rental By Owner

Showing 20 Of 24 Vacation Rentals
  • Property-1 Image 1
    House $599 / Nightly
    • 3 Bed
    • 2 Baths
    • (8) Exceptional
    Chilmark, MA

    Mid-Century modern glass house, in Menemsha, on Marthas Vineyard Designed by a Frank Lloyd Wright apprentice, this all glass house, embodies the integration of... ...more

  • Property-2 Image 1
    Cottage $360 / Nightly
    • 3 Bed
    • 1 Baths
    • (5) Very Good
    Chilmark, MA

    Renovated historic barn (1870). Lofts converted to open bedrooms, private main bedroom, roomy living room/dining/kitchen area. Private deck. Large yard with stone... ...more

  • Property-3 Image 1
    House $652 / Nightly
    • 4 Bed
    • 3 Baths
    • (3) Exceptional
    Chilmark, MA

    Renovated historic house (1870). Large living room/dining area. 4 bedrooms sleep 8 plus sofa sleepers. 3 full bathrooms. Located between Lucy Vincent and... ...more

  • Property-4 Image 1
    House $522 / Nightly
    • 4 Bed
    • 3 Baths
    • (9) Exceptional
    Chilmark, MA

    A recently renovated country home located in the Vineyard's most idyllic town. This 4 bedroom/2 full bath home offers you an updated kitchen, open living area,... ...more

  • Property-5 Image 1
    Cottage $920 / Nightly
    • 4 Bed
    • 2 Baths
    • (7)
    Chilmark, MA

    Dream on the Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" Make... ...more

  • Property-6 Image 1
    House $403 / Nightly
    • 4 Bed
    • 2 Baths
    • (5) Good
    Chilmark, MA

    Island Romance Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" Island... ...more

  • Property-7 Image 1
    House $287 / Nightly
    • 3 Bed
    • 2 Baths
    • (12)
    Chilmark, MA

    Superb fields-to-ocean-to-islands views from this charming guesthouse, on a historic Chilmark property. You'll enjoy a wealth of beach options. Squibnocket beach... ...more

  • Property-8 Image 1
    Cottage $312 / Nightly
    • 2 Bed
    • 2 Baths
    • (5) Exceptional
    Chilmark, MA

    Charming rustic cottage located a short distance off South Rd just past Abels Hill in Chilmark. Chilmark is very rual with rolling hills and stone walls. Water... ...more

  • Property-9 Image 1
    House Select Dates for Price
    • 4 Bed
    • 3 Baths
    • (2) Exceptional
    Chilmark , MA

    A hidden gem tucked in the woods of the desirable Tea Lane neighborhood. A freshly painted interior, brand new second floor carpeting, conservation grade Birch... ...more

  • Property-10 Image 1
    House $532 / Nightly
    • 3 Bed
    • 3 Baths
    • (4) Exceptional
    Chilmark, MA

    This charming and simple rustic shingled cottage is located in the quiet Spring Point area of Chilmark along Vineyard Sound. A full size deck extends across the... ...more

  • Property-11 Image 1
    House Select Dates for Price
    • 3 Bed
    • 1 Baths
    • (5) Wonderful
    Chilmark, MA

    Cancellation Policy: A full refund will be given if we are able to re-rent a canceled week. You can enjoy the Menemsha Sunsets from your own private deck.... ...more

  • Property-12 Image 1
    House $492 / Nightly
    • 2 Bed
    • 1 Baths
    • (15) Wonderful
    Chilmark, MA

    Our antique cottage offers an idyllic up island experience, including privacy, tranquility, and breathtaking views from sun up to sunset. Walk down the wooden... ...more

  • Property-13 Image 1
    House $450 / Nightly
    • 4 Bed
    • 3 Baths
    • (2) Exceptional
    Chilmark, MA

    Situated on the quiet end of the Island, yet only a 15 minute drive from Vineyard Haven, this rustic, authentic Chilmark farm house boasts four bedrooms, two... ...more

  • Property-14 Image 1
    House $552 / Nightly
    • 3 Bed
    • 2 Baths
    • (9)
    Chilmark, MA

    Everything you think of when you dream of Chilmark... pastoral rolling 2+ acres with water views and stone walls. Ideal location less than 1.25 miles to all... ...more

  • Property-15 Image 1
    House $956 / Nightly
    • 4 Bed
    • 2 Baths
    • (1) Exceptional
    Chilmark, MA

    Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house... ...more

  • Property-16 Image 1
    House $571 / Nightly
    • 2 Bed
    • 2 Baths
    Chilmark, MA

    Perfect for two couples or a small family, this is a fully furnished one story ranch house overlooking Menemsha Bight. The large wood-paneled center living room... ...more

  • Property-17 Image 1
    Estate Select Dates for Price
    • 4 Bed
    • 3 Baths
    • (43)
    Chilmark, MA

    One of Chilmark's most stately and classic farmhouses,which has been thoughtfully and fashionably edited and updated with every modern comfort. The house is in a... ...more

  • Property-18 Image 1
    Cottage $624 / Nightly
    • 5 Bed
    • 3 Baths
    • (1) Exceptional
    Chilmark, MA

    Enter our vacation world up a 0.2 mile paved driveway through the woods to the private hilltop with only two other houses. Open the gate and delight at the... ...more

  • Property-19 Image 1
    House $409 / Nightly
    • 4 Bed
    • 3 Baths
    • (19) Wonderful
    Chilmark, MA

    Next Season We will be posting prices and taking reservations on the day after Labor Day. We do have a number of guests that love to return at the same time each... ...more

  • Property-20 Image 1
    Cottage $651 / Nightly
    • 2 Bed
    • 1 Baths
    • (3) Exceptional
    Chilmark, MA

    Built as guest house, this 800 square foot cottage has two bedrooms, gourmet kitchen, bright living dining room, and a queen bed room and a detached bunkhouse... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Chilmark. Many accommodations in Chilmark provide "Non Smoking Only", there are 67, or there are 57 of Vacation Rentals in Chilmark with a "Children Welcome", there are also 48 with "Fishing", which is another great reason to visit Chilmark.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Chilmark. The most expensive month of the next 12 months is in July, where prices hit an average of $451 a night. In , prices will hit an average low of $0 per night.