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

Chilmark, Massachusetts
$368 avg/night
Bed 2

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 4

Max Sleeps

Chilmark Guest House

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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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 800 Sq Ft (74 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Garden Gas Grill Patio
  • BATHROOMS

    1 Bathroom Hair Dryer Towels Provided
  • LANGS SPOKEN

    English French German Italian Spanish
  • THINGS TO DO

    Birdwatching Nearby Cycling Nearby Kayaking Nearby Marina Nearby Power Boating Nearby Scuba Diving Nearby Snorkeling Nearby Swimming Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Books Games TV
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair
  • LOCATION HIGHLIGHTS

    In A Village Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Note From Host: Smoking Is Not Permitted Anywhere On The Premises. Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 4

Map Map

School District Rates & Availability

Review Review

  • Chris E.

    Submitted Nov 1, 2025

    Stayed Oct 28, 2025

    Nice comfortable place, good for a relaxing time.

  • Charles M.

    Submitted Oct 2, 2025

    Stayed Sep 18, 2025

    Excellent trip, no surprises exactly what I hoped for.

  • Judy l.

    Submitted Aug 21, 2025

    Stayed Aug 14, 2025

    We had large carpenter ants from the beginning. We got in touch with Nicole who said we were on a list to treat them. Contacted her three times. We bought ant traps and sprayed with Raid. See picture below. Thermostat didn’t work after day one. More phone calls but still on a list. Never repaired. Had no AC the whole week. See photos below. Otherwise bed was super comfortable and shower good, kitchen was well stocked

  • Glenn M.

    Submitted Aug 21, 2025

    Stayed Aug 5, 2025

    My experience was simply amazing. Nestled in Chilmark in the woods was just an wonderful experience. However we all felt safe and the home was just right. I would sit on the deck for hours and no mosquitos.

  • Eve G.

    Submitted Aug 5, 2025

    Stayed Jul 27, 2025

    Great place. A bit hard to find at first but once we got there, read the house guide and told of better route to North Rd. Very happy with property and communication. Thank you!

  • Ellen L.

    Submitted Jun 26, 2025

    Stayed Jun 21, 2025

    Charming cottage in a nice, quiet part of the island. Very close to nearby beaches and fish markets, as well as the Chilmark General Store that was super cute. Bed was so comfortable and water pressure/water temperature was great too. Only downside is that the last day, a bunch of giant ants kept crawling into the house - not sure why as we didn't have any food out. Perhaps because it was really hot outside?

  • MARIA A.

    Submitted Apr 25, 2025

    Stayed Apr 21, 2025

    Very good

  • ed m.

    Submitted Sep 28, 2024

    Stayed Sep 24, 2024

    Very clean. Bed was incredibly comfortable

  • Richard G.

    Submitted Sep 27, 2024

    Stayed Sep 22, 2024

    A perfect cottage in the woods with all the amenities you could desire.

  • Danielle V.

    Submitted Sep 27, 2024

    Stayed Sep 14, 2024

    Had a lovely stay for a week in September with our dog! House is clean, well stocked and in a very private location. The house is perfect for a couple or small family. We could not have asked for a better stay! Highly recommend!

  • Dave D.

    Submitted Sep 9, 2024

    Stayed Sep 1, 2024

    The surrounding woods with trails were peaceful and a joy to walk on. The cottage was clean and tidy. Would highly recommend.

  • Kevin D.

    Submitted Aug 25, 2024

    Stayed Aug 10, 2024

    Private with beach access minutes away.

  • Monika C.

    Submitted Aug 9, 2024

    Stayed Jul 21, 2024

    We had such a lovely time staying at this house. It was absolutely immaculate inside and appointed with everything we could need and more. The house is light and airy inside, which helped when we had a few days of rain. The location is secluded in the woods (be careful, we did find ticks on us) but a short drive away from the beaches. We will definitely be back

  • Julia L.

    Submitted Jun 3, 2024

    Stayed May 31, 2024

    This is a nice small place. The neighbor yelled at me for walking my dog on the road that you are told to drive in on. There was NO hot water and requests to fix it were met with lots and lots of text messages from vacasa who after 8 hours on day 2 sent a local vacasa person (not a plumber or electrician or hvac person) to the property who accessed the locked cellar and the water heater to learn that it was unplugged. After plugging it in and checking the pilot he was very polite but left. I was told it would take an hour but it was never restored and there was no way to check or get someone to fix. It also begs two questions- did you not clean with hot water? And how would the dishes have gotten clean? Gross. And why would it be unplugged? The vineyard in early June with no hot water is rough when you go to fish in a fishing tournament. Or to the beach. Or want to be clean. The house was unlocked when I arrived and the slider door was wide open and so a bird had taken up residence and we know what birds do… so that was unsafe and also gross. I spent some time getting the bird to leave. Over all I didn’t spend my time the way I had planned. Vacasa now dominates the management market on the vineyard. After having rented homes there for 20 years it is now very challenging to find one not managed by this company that clearly has nice people on island trying to manage but they can’t actually get it done. Requests for a refund have been met with more text messages no action.

  • arianne s.

    Submitted May 6, 2024

    Stayed Dec 31, 1969

    Close to Menemsha, and not too far from the Lucy Vincent and Squibnocket beaches. Nice yard and deck with privacy. North Tabor Farm was just down the street where we found great food to stock our kitchen. Kids loved their room and the play structure. We had a great family vacation and would definitely return.

  • Adam P.

    Submitted Apr 24, 2024

    Stayed Dec 31, 1969

    This was an amazing house to stay in. The kitchen is well equipped, the bathroom has no issues, the kids' bedroom has a few toys, our bedroom had a huge comfortable bed, and the living area offers a fantastic view. The BBQ is working well—it is brand new. The swing and slide outside were a great hit. I wish to come again. The location worked perfectly for us.

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Total

Includes taxes and fees
$368+
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