Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

Chilmark Guest House

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

Tucked away in a private glen on three secluded acres, this light-filled home in Chilmark is Martha's Vineyard at its most peaceful. It's the perfect escape for beach-goers, as it sits within minutes of Menemsha (three miles), Lucy Vincent Beach (four miles), and Squibnocket Beach (five miles).
The house enjoys a beautiful, natural setting, with thickets of woods surrounding the grassy lawn. On summer mornings, ride your bikes or walk less than two miles to the tranquil expanse of Great Rock Bight Preserve. Upon your return, linger outside on the deck and sip a steaming cup of coffee in a rocking chair.

It's a joy to come home after a day at the beach, as you light the gas grill, set the outdoor table for a sunset dinner, and watch the kids release any lingering energy on the outdoor play structure. Back inside, lofty ceilings, exposed cross beams, and large panes of glass bring in an abundance of light and nature. As a result, you'll feel surrounded by the island's beauty as you cook in the kitchen, play board games at the table, and stream movies in the living room.

Both bedrooms open to the deck, one of which is a charming children's room with bunks and a selection of toys and books. A private washer/dryer and complimentary WiFi are provided for your comfort and convenience as well.

Things to Know

If you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.
Parking notes: There is free parking available for 3 vehicles.

Please note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!

Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.