VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

Show moreless regions

This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Other areas nearby to Chilmark:

Recent Chilmark property reviews

  • Great House, Great Setting

    "This house is filled with light. The BR, LR, kitchen, screened porch and deck all face the ocean. It's up a hard-packed, typical Vineyard dirt road, easy to travel with car or mountain bike. Perfect location, between West Tisbury and Chilmark with easy access to OB and E-town. Small but well-appointed kitchen, good firm bed, excellent outdoor shower, easy access to boats no more than 20 feet from the dock. Dark skies at night make for great constellation sightings."
    Guest: Larry Date of Stay: July 2014 Review Submitted: August 5, 2014
    View listing
  • Mill Valleyian

    "We loved this property and had a wonderful vacation. The highlights were the incredible beach ( the kids loved the adventure of crossing the pond to get to the beach) and having access to tennis courts that were nearly always empty. The house was well equipped for our family of five, with a brand new barbeque and beach equipment such as towels, umbrella and cooler. The owner was incredibly helpful and available to us for questions and advice. ( The house has a great book with local tips). Up island is the way to go for beauty and quiet."
    Guest: janet Date of Stay: June 2011 Review Submitted: August 18, 2011
    View listing
  • Chilmark house

    "Very nice and clean "lodge" like home in a farm land setting with 100 acre views and comfortable air conditioned accommodations. Fishing with the owner is a special and memorable experience every time we visit. The private beach is a very nice bonus to this rental. Would recommend this property for families or up to 5 couples."
    Guest: jerry Date of Stay: July 2012 Review Submitted: July 23, 2012
    View listing
  • Unforgettable vacation spot

    "My family enjoyed a week full of rest, fun, and the most beautiful Up Island beaches in this comfortable and affordable house. The view is gorgeous! The porch and enclosed lawn area was perfect for my kids to play in and the TV and games and upstairs area kept them happy inside. We can't wait to return!"
    Guest: Kidlitter Date of Stay: August 2009 Review Submitted: May 18, 2010
    View listing

Chilmark Travel Tips

Experience the Best of Martha's Vineyard with Chilmark Vacation Rentals

Chilmark, Massachusetts is a 34-square-mile town on the western end of the island of Martha's Vineyard steeped in history and culture. The town features buildings that are more than one hundred years old and still in use. The town hall was built in about 1897, and an old church nearby was built in 1843. And children from pre-kindergarten through fifth grade still learn in the one-room schoolhouse that was put up in about 1850. When you stay in Chilmark vacation rentals, you get to experience a little piece of Martha's Vineyard as it was more than a century ago.

Chilmark's Local Fare: There's Something for Everyone

Though the town of Chilmark is small, the agriculture there is strong and varied. If you're interested in eating and buying organically and locally, Chilmark has a wide array of products to offer you. During your stay at one of the Chilmark beach homes, you can drink milk from local cows, eat eggs laid by free-range chickens, nibble on bacon from island-raised pigs, or cozy up in some wool shorn from the town's sheep. Of course, there's always a fresh catch of the day up for grabs at the town's two fish markets. And don't forget dessert! Get in line at Chilmark Chocolates to experience the town's trademark sweet.

The Perfect Small-Town Vacation

When it comes to Martha's Vineyard lodging, Chilmark vacation rentals have it all: access to amazing beaches with spectacular sunsets; delicious, fresh local food; top-notch historical sites; and unique, exciting live theater. The tiny town has all the activities and attractions you could ask for in a great vacation destination, and it's all wrapped up in a quaint, peaceful package that's full of original Martha's Vineyard character.

Sponsored Advertisement