Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.

Chilmark, Massachusetts
$819 avg/night Minimum Stay 2 Nights
Bed 2

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 3

Max Sleeps

Night 2 nights

Min Stay

Petite Mid-century, renovated guest house is private with own driveway, yard, and easy walk to Menemsha Pond, harbor, public beach, Galley restaurant & ice cream, fish markets. Views of Pond, Vineyard sound, Aquinnah. 2 bedrooms, galley kitchen, living room wrapped in sliding glass doors out to deck. Beach pass to amazing Lucy Vincent or Squibnocket beaches avail. Well behaved dogs welcome, streaming TV, Wifi, A/C, heat, laundry + level-2 EV charger.

Serene and calming location ideal for unwinding, unplugging, relaxation. unexpected daily visits from local bunnies, deer, hawks. At night enjoy clear starlit skies or summer fireflies.

Outdoor furniture included upholstered couch with small table, lounge chairs with giant umbrella, picnic table, weber gas grill. Close to Chilmark Store, Chilmark Community Center. Nestled in nature with a small lily pond onsite & ideal for disconnecting. .4 miles (7 mins) walk to Pond boat launch - great for paddle boarding or fishing (BYOB). Close to Menemsha Inn & Beach Plum Inn. Great dirt roads for running or walking. Loads of hiking trails nearby. Enjoy incredible light + sunsets from the deck.

Recently renovated with reclaimed barn door, translucent panels, new kitchen +bath. Simple Menemsha living with amenities. This cozy home is ideal for a single person, couple, or 3 close friends. A previous guest have compared it to a small houseboat as it's cozy inside. Enjoy outdoor shower, professionally manicured grounds, and bubbling brook next to house for natural ambiance. Kitchen has all the modern amenities, microwave, dishwasher and is fully stocked.

Feel like a local enjoying eggs from a nearby farmstand, or fresh fish from Larsen's market. Large grass yard great for pups.

NOTE - Our Main house just across a gentle stream via bridge is double the size of this home and may be rented together (if both available). Search VRBO # 2604149.

Bookings for next season open in October . Reach out if interested.

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

Feature Features

  • PETS

    2 Total Pets Pet Friendly Welcoming Dogs Only
  • BEACH

    Beach Sun Loungers Beach Towels Near The Beach
  • 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

    Eco-friendly Cleaning Products Used Recycling Unit Size: 480 Sq Ft (45 Sq M) Uses Some LED Lighting
  • KITCHEN

    Cookware/dishes/utensils Dishwasher Electric Kettle Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Electric Car Charging Station On Site Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Garden Outdoor Furniture Patio
  • BATHROOMS

    Bathtub Or Shower Eco-friendly Toiletries Hair Dryer Outdoor Shower Shampoo Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English German Hungarian Spanish
  • THINGS TO DO

    Fishing Nearby Hiking Nearby Hiking/biking Trails Nearby Kayaking Nearby Marina Nearby Mountain Biking Nearby Surfing/body Boarding Nearby Swimming Nearby Water Skiing Nearby Water Sports Equipment
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Rural Location Near The Bay On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    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 : 3

Map Map

School District Rates & Availability

Review Review

  • tim d.

    Submitted Oct 22, 2025

    Stayed Oct 17, 2025

    yes climate control worked perfect. Very Pet friendly great safe yard for dogs too play.

  • Kathryn M.

    Submitted Sep 27, 2025

    Stayed Sep 20, 2025

    A very special place—we loved the location, walking to Menemsha, the access to the pond for paddle boarding, the sunset views—everything!

  • Susan L.

    Submitted Sep 13, 2025

    Stayed Sep 6, 2025

    Incredible location-vistas, nature sounds, secluded, but walkable into Menemsha Harbor. Chris was super responsive and the house had everything we needed!

  • Mark E.

    Submitted Sep 8, 2025

    Stayed Aug 29, 2025

    Christian thought of everything. Extremely comfortable and livable space. One of the most stunning locations on the island for sure.

  • Beth H.

    Submitted Aug 18, 2025

    Stayed Aug 13, 2025

    Loved loved this house and location! Absolutely beautiful setting and fantastic home. Small and quaint and easy to manage, especially with the dogs. Clean, and extremely well-maintained. We absolutely loved it and would definitely come back again and again!

  • Ellen C.

    Submitted Aug 13, 2025

    Stayed Aug 9, 2025

    Wonderful home! Perfect size, stunning views, and everything you could possibly need for a stay in Chilmark!

  • Zack S.

    Submitted Jul 5, 2025

    Stayed Jun 28, 2025

    We spent two weeks on Cape Cod and Martha’s Vineyard this summer, and the few days we spent here were the best. The communication with the host reserving the property, getting great advice regarding scheduling ferries, and information on Lucy Vincent Beach was incredible! We were able to go to Lucy Vincent Beach as a result of renting here and it was a beautiful few days. It was an incredible experience. Never have had a more communicative host.Very thoughtfully laid out home. Heating and air was excellent, a beautiful deck overlooking the pond, and incredibly clean. You’re less than a mile to Chilmark General Store and Chilmark Tavern, as well as to Menemsha. It’s a 20 minute drive to the other larger towns on the other side of the island. I definitely recommend people stay here if they want to enjoy the beauty of Martha’s Vineyard.

  • Debra S.

    Submitted Jun 23, 2025

    Stayed May 31, 2025

    The house is in a beautiful setting close to stores and beach. A bit small for 3 adults but spotless and tasteful. The kitchen was very clean which I especially appreciated (particularly after a few sticky kitchens in expensive rentals). The picnic table outside allows to extend the eating space to the garden. Our hosts were responsive and discreet,

  • Eileen D.

    Submitted Jun 20, 2025

    Stayed Jun 15, 2025

    Perfect stay in this well appointed summer cottage. Amazing views! Enjoyed spending time the start and end of the day on the deck taking in the views. Very clear communications from host. Welcome package was very informative on hikes and local shops.

  • Beth G.

    Submitted May 31, 2025

    Stayed May 26, 2025

    The photo says it all.Thank you Christian.

  • Greg D.

    Submitted May 13, 2025

    Stayed May 3, 2025

    The guest house is small and quaint. Floor to ceiling glass over looking the yard and Menemsha pond make for a peaceful setting. Christian is an excellent host with great communication.

  • Neville A.

    Submitted May 4, 2025

    Stayed Apr 30, 2025

    The Guest House was perfectly located in a peaceful rural setting overlooking the water. The house itself was well appointed, clean and had everything we needed. The description in the listing was accurate and the communication with Christian was very prompt and helpful. In addition the weather was fantastic! We certainly hope to return. Thanks Christian for a wonderful time.

  • Erin L.

    Submitted Oct 14, 2024

    Stayed Oct 9, 2024

    We were in town for a wedding in Chilmark and the property was exactly what we needed!

  • Linda P.

    Submitted Oct 7, 2024

    Stayed Sep 29, 2024

    Perfect location. Clean and cozy. Private yard. A bit small, but was great for two adults and our dog! Christian was always available for any questions. He's a great host. Beautiful sunsets looking west across Menemsha pond, and a short walk to beach.

  • katherine M.

    Submitted Sep 30, 2024

    Stayed Sep 21, 2024

    The cottage has been very thoughtfully updated without losing its simple beach charm. Wonderful walls of windows flow into the open landscape and water on the horizon. It’s a cozy space perfect for a couple or a small young family - although we visited in the fall, can imagine it would feel like true indoor/outdoor living during the summer months when the weather allows. A quiet dirt road on the sleepy side of the island was perfect for long walks with the dog each morning with our coffee. Would very happily stay again.

  • brian b.

    Submitted Sep 13, 2024

    Stayed Aug 25, 2024

    Beautiful and peaceful

  • Robert D.

    Submitted Jul 14, 2024

    Stayed Jul 5, 2024

    This could not be more of a relaxing spot, located in a nature preserve area on the quiet side of MV. We were welcomed by many types of birds and a family of bunnies during our stay. It is very quiet and peaceful, with a few great spots for dining and access to resident only beaches which are never crowded. The deck is huge and the wrap around windows in the living room were really special. My only suggestion to other vacationers is to be aware the cottage is small, and the main bedroom is tight with only a full size matress, so it is a bit challenging if you’re used to a larger bed & bedroom. Overall my wife and I had a really nice & relaxing time.

  • Lincoln R.

    Submitted Jun 22, 2024

    Stayed Jun 15, 2024

    Beautiful spot for a couple, quiet except for songbirds and the Menemsha Harbor bell a mile or so distant. Big beautiful view, including Gay Head Lighthouse light. Private and peaceful.

  • Richard S.

    Submitted Jun 5, 2024

    Stayed May 27, 2024

    This beautiful little cottage with a view of the harbor was a perfect escape from our City life. The space is smartly laid out and the living room with glass walls on three sides is the perfect spot to relax with a book -- it was equally beautiful to watch a storm approach as it was to watch the sun set.

  • Amanda A.

    Submitted Jun 4, 2024

    Stayed May 31, 2024

    This spot was wonderful- even better than we anticipated from the online advertising. The yard is very private, with a spectacular view and walkable go various spots. Everything is clean and the kitchen essentials are well stocked. The host is very organized, great communication and everything went smoothly.

  • Molly M.

    Submitted Jun 1, 2024

    Stayed May 19, 2024

    Went here in May 2024 for my husband's 50th & a change of scenerty. Have been to MV many times but never stayed in Menemsha. This home was lovely - clean, serene, great yard for our mutt to run around. A few things to note for guests: it is in a very remote part of the island, so there is a lot of drive time (was fine for us); there are blackout curtains / shades, so you wake up with the sun (bring an eye mask); make sure you load up on groceries before you get to the house (especially ice); Chilmark is a dry town, so if you head to Chilmark Tavern (delightful place + 5 min drive from the house!) be sure to bring your favorite adult bev. Christian was very communicative the entire stay - super helpful. All in all, it was a really nice getaway.

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Total

Includes taxes and fees
$819+
View details