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Vacation rentals in Chilmark

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Top-rated vacation rentals in Chilmark

Guests agree: these stays are highly rated for location, cleanliness, and more.

Vineyard Haven Walk to Ferry
Entire residential home · 6 guests · 5 beds · 2 baths

Vineyard Haven Walk to FerryI love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, garden and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

Cozy Waterfront Cottage, Newly Remodeled!
Entire residential home · 6 guests · 4 beds · 2 baths

Cozy Waterfront Cottage, Newly Remodeled!Beautifully upgraded waterfront cottage in Menemsha. All new linens, furnishings, paint, and HVAC system. Enjoy stunning sunsets from the second-story deck. Private and peaceful but conveniently located just a short drive or bike ride to Menemsha or Chilmark. Relax and take in the breathtaking views from almost every room.

2 BR- Private Home in  Chilmark Woods with Hot Tub
Entire residential home · 4 guests · 2 beds · 1 bath

2 BR- Private Home in Chilmark Woods with Hot Tub2 Bedroom home in wooded Chilmark neighborhood. 25 minute walk to Alleys General store and West Tisbury Center and Library. 5 Minute drive to Lucy Vincent Beach and Chilmark town center and 20 minute drive to Gay Head Cliffs. Spacious outdoor space with 8 people outdoor dining, fire pit, BBQ, 6 person hot tub and outdoor shower.

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Popular amenities for Chilmark vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Chilmark

  1. Private room
  2. West Tisbury
The Heart of West Tisbury
  1. Entire cottage
  2. West Tisbury
Cozy Cottage
SUPERHOST
  1. Entire rental unit
  2. Tisbury
Mayflower Haven
SUPERHOST
  1. Entire rental unit
  2. Chilmark
New Chilmark Gem
SUPERHOST
  1. Entire residential home
  2. Tisbury
Carolyn's Vineyard Haven
SUPERHOST
  1. Private room
  2. Tisbury
Spacious 2 Room Suite in Vineyard Haven
SUPERHOST
  1. Entire residential home
  2. Tisbury
Private Wooded Hillside New and Spacious Studio
SUPERHOST
  1. Entire guesthouse
  2. Chilmark
Beautifully Renovated 1800s Chilmark Barn
  1. Entire residential home
  2. Chilmark
Charming Chilmark Cottage
SUPERHOST
  1. Entire rental unit
  2. Tisbury
Quaint Vineyard Escape
SUPERHOST
  1. Entire guesthouse
  2. Chilmark
Beautiful Guest House in Chilmark
SUPERHOST
  1. Private room
  2. Tisbury
Serendipity Encore

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