About This Property

Welcome to Hennessey Cottage at 22 Plantingfield Wood Circle in Edgartown, MA. This charming cottage is located just half a mile from downtown Edgartown, one of the most beloved villages on Martha's Vineyard. It's a short walk to local restaurants, cafes, and boutiques. The cottage has a rich artistic history — painter Ray Ellis once lived and worked here, inspired by the island's unique light. You'll find his prints throughout the cottage along with coffee table books he created with Walter Cronkite. The property features four bedrooms and three and a half bathrooms, a studio loft with kitchenette, and wonderful outdoor spaces including a jacuzzi, screened-in back patio, fire pit, gas grill, and a spacious yard perfect for lawn games. Bikes are available in the garage for exploring the island.

What This Place Offers

Outdoor Shower
Jacuzzi
Screened Patio
Fire Pit
Bikes
Board Games
Espresso Machine
BBQ Grill
Outdoor BBQ grill
Washer & Dryer
In-unit laundry
Smart TV
Smart TV with streaming services
WiFi
High-speed internet throughout the property
Free Parking
Free on-site parking

Local Tips and Recommendations

Behind the Bookstore
Fun bar and cafe, great for morning coffee
Rosewater
Awesome breakfast spot
Espresso Love
Great breakfast sandwiches and coffee
The Harborview Hotel (Bettini)
Favorite hotel with a wonderful restaurant and bar. Enjoy cocktails on their expansive front porch with harbor views
The Newes
Favorite for lobster rolls and burgers, historical spot
Alchemy
Fancy restaurant and great bar
The Atlantic Fish and Chop House
Amazing food and ocean views (no reservations, not open off-season)
The Shanty
Family-style restaurant with ocean views, great lobster rolls and cocktails (not open off-season)
Faraway Hotel (Pelican Club)
Swanky outdoor bar, perfect for sushi and cocktails
19 Raw Oyster Bar
Great drinks, sister restaurant Prime is a fantastic steakhouse
The Wharf
Fun bar with lots of MV culture
Also great: Rockfish, Port Hunter, Covington
South Beach in Katama
Oak Bluffs
Cute seaside town with the famous Gingerbread House Village
Island Alpaca
Adorable alpaca farm
Edgartown Lighthouse
Aquinnah Cliffs in Chilmark
The Dunes on Chappaquiddick Island
Sheriff's Meadow Sanctuary nature trail
not far from the house at 51 Plantingfield Way, a gorgeous way to walk into town
Edgartown is very walkable (biking on cobblestone streets is not recommended)
Martha's Vineyard Transit Authority bus
closest stop is half a mile away on Church Street (next to 19 Raw Oyster Bar). Buses have bike racks.
Rent a car in Oak Bluffs or Vineyard Haven
Uber is available
Bike rentals available on the island

Check-in and Check-out

Check-in

Contact Jackie at 401-743-9512 for the door code. To unlock: Press the symbol first, then enter the four-digit code. Note: The front door handle can be tricky — please make sure not to slam it. Pull the latch tightly when leaving. Back patio doors in kitchen: Close the door, then hold the handle up all the way to latch, lock, and unlock.

Check-out

Check-out: 11:00 AM • Please strip beds and place used towels in the laundry room • Turn off all lights and lock all doors • Return keys to the lockbox • Ensure all windows are closed and thermostat is set to 65°F

Emergency Information

Contact Jackie at 401-743-9512 for any issues. Sunscreen and insect repellent are in the bottom island drawer on the right-hand side. Beach towels are in the garage in the wooden cabinet. Extra toilet paper, paper towels, and towels are in the basement linen closet.