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4-Season Guest House on Historic Chilmark Estate

Entire guesthouse
hosted by Jessica
  1. 2 guests
  2. 1 bedroom
  3. 1 bed
  4. 1 bath
Jessica is a Superhost
Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.
Great location
100% of recent guests gave the location a 5-star rating.
Great check-in experience
100% of recent guests gave the check-in process a 5-star rating.


Every booking includes free protection from Host cancellations, listing inaccuracies, and other issues like trouble checking in.
Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store.
Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

The space
Continental breakfast supplies provided on check-in including honey from our bees and the best granola.
Owner lives in main house adjacent. Old-style Chilmark charm on historic property. Hear the ocean at night if the wind is right, and the stars are always amazing. Cool, casual and comfortable.
1 mile from Lucy Vincent Beach and Squibnocket Beach.

Drive on pass to Lucy Vincent and Squibnocket beaches available for purchase at Chilmark Town Hall (town requires purchase of a seasonal pass) - otherwise free walk-on beach passes are provided to both beaches.

To accommodate more family members consider also booking my other listing on the property: Beautifully Renovated 1800s Chilmark Barn - sleeps 4.

Where you'll sleep

1 queen bed

What this place offers

Garden view
Beach access
Free parking on premises
Private patio or balcony
Shared backyard – Not fully fenced
Indoor fireplace: wood-burning
Luggage dropoff allowed
Hair dryer

Where you’ll be

Chilmark, Massachusetts, United States

Chilmark is the best place in the world. Gorgeous beaches and walks, the best people, great food. Quiet and restorative.

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5.0 out of 5 stars from 60 reviews

Hosted by Jessica

Joined in September 2017
  • 125 Reviews
  • Identity verified
  • Superhost

Jessica is a Superhost

Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.
  • Response rate: 100%
  • Response time: within an hour
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Rated 5.0 out of 5 from 60 reviews.