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Chilmark 1,910 rentals
    •  
      $400 avg/night
      4 Bedrooms, Sleeps 10
      3
    •  
      $500 avg/night
      4 Bedrooms+, Sleeps 6
      5
      Frequently Booked
    •  
      $276 avg/night
      3 Bedrooms, Sleeps 8
      6
    •  
      $450 avg/night
      3 Bedrooms, Sleeps 6
      5
    •  
      $643 avg/night
      5 Bedrooms+, Sleeps 10
    •  
      $502 avg/night
      5 Bedrooms, Sleeps 10
      8
    •  
      $388 avg/night
      4 Bedrooms, Sleeps 8
      14
    •  
      $300 avg/night
      3 Bedrooms, Sleeps 8
      6
    •  
      $357 avg/night
      3 Bedrooms+, Sleeps 8
      12
    •  
      $686 avg/night
      4 Bedrooms, Sleeps 8
      10
    •  
      $1,000 avg/night
      4 Bedrooms, Sleeps 11
    •  
      $309 avg/night
      2 Bedrooms, Sleeps 4
      3
    •  
      $395 avg/night
      3 Bedrooms, Sleeps 6
      4
    •  
      $357 avg/night
      2 Bedrooms+, Sleeps 6
      3
    •  
      $445 avg/night
      2 Bedrooms, Sleeps 5
      1
    •  
      $164 avg/night
      Studio, Sleeps 2
      10
    •  
      $400 avg/night
      3 Bedrooms, Sleeps 8
    •  
      $1,000 avg/night
      7 Bedrooms, Sleeps 18
    •  
      $586 avg/night
      5 Bedrooms+, Sleeps 11
      1
    •  
      $471 avg/night
      5 Bedrooms, Sleeps 10
    •  
      $200 avg/night
      4 Bedrooms, Sleeps 8
      8
    •  
      $171 avg/night
      4 Bedrooms+, Sleeps 11
      14
    •  
      $398 avg/night
      5 Bedrooms, Sleeps 10
    •  
      $413 avg/night
      5 Bedrooms, Sleeps 8
    •  
      $171 avg/night
      1 Bedroom, Sleeps 2
      6
    •  
      $528 avg/night
      4 Bedrooms, Sleeps 8
      1
    •  
      $467 avg/night
      4 Bedrooms, Sleeps 7
      5
    •  
      $1,357 avg/night
      3 Bedrooms+, Sleeps 8
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      View listing for price
      4 Bedrooms, Sleeps 8
    •  
      $393 avg/night
      3 Bedrooms, Sleeps 7
      1
    •  
      $464 avg/night
      3 Bedrooms, Sleeps 8
      4
    •  
      $514 avg/night
      3 Bedrooms+, Sleeps 8
      7
    •  
      $286 avg/night
      3 Bedrooms, Sleeps 7
      3
    •  
      $414 avg/night
      4 Bedrooms, Sleeps 8
      2
    •  
      $143 avg/night
      2 Bedrooms+, Sleeps 6
      8
    •  
      $3,076 avg/night
      4 Bedrooms+, Sleeps 12
      1
    •  
      $1,000 avg/night
      4 Bedrooms, Sleeps 8
    •  
      $250 avg/night
      2 Bedrooms, Sleeps 5
      5
    •  
      $378 avg/night
      3 Bedrooms, Sleeps 7
    •  
      $286 avg/night
      3 Bedrooms+, Sleeps 7
    •  
      $466 avg/night
      3 Bedrooms, Sleeps 8
      1
    •  
      $872 avg/night
      4 Bedrooms, Sleeps 8
    •  
      $1,143 avg/night
      5 Bedrooms, Sleeps 14
      1
    •  
      $283 avg/night
      2 Bedrooms, Sleeps 4
      3
    •  
      $1,000 avg/night
      7 Bedrooms, Sleeps 12
    •  
      $457 avg/night
      3 Bedrooms, Sleeps 6
      4
    •  
      $429 avg/night
      3 Bedrooms, Sleeps 6
      3
    •  
      $429 avg/night
      3 Bedrooms, Sleeps 6
      5
    •  
      $443 avg/night
      6 Bedrooms, Sleeps 12
    •  
      $300 avg/night
      3 Bedrooms, Sleeps 4
Other areas nearby to Chilmark:

Recent Chilmark reviews

  • Definitely will return

    Charles M.

    "We recently visited this wonderful Vineyard home. It was perfect. Centrally located. Very quiet , Nature surrounding us, wild turkeys in yard, just absolutely beautiful. Everything we needed for our vacation. Being so close to Alley's was perfect for our son. The house has so much charm. I would spend each morning watching the sunrise in the window bench in the living room. We will definitely return!"
    • Stayed September 2016
    • Submitted September 27, 2016
    • Source VRBO
    View this listing
  • Beautifully decorated with all the comforts of home

    Erin I.

    "Tucked away in the woods, this felt like a private retreat but still had easy access to local beaches and the rest of the island. The decor is tasteful, simple and beautifully done. The owners thought of everything you need from kitchen essentials (coffee pot, bottle opener, etc) to beach towels. We only turned on the TV once, but it's nice that it's there for a rainy day. The wooden swing is a charming detail for an afternoon book with a glass of wine. I would highly recommend and we definitely plan to return."
    • Stayed July 2016
    • Submitted September 1, 2016
    • Source VRBO
    View this listing
  • Beautiful Property and very spacious

    John A.

    "Beautiful house, great area, very spacious, clean, and it was great staying there!"
    • Stayed November 2016
    • Submitted November 29, 2016
    • Source VRBO
    View this listing
  • Relaxing family vacation!

    Jeanne M.

    "My husband, myself and two older teens (and family dog) thoroughly enjoyed our week at this Spring Point/Chillmark cottage. The cottage was extremely clean and offered everything you would need for your stay including dishwasher, washer/dryer, grill, not to mention beach chairs, beach towels, games and books and more. The decor is simple and comfortable. The back deck with views of the sound is amazing, offering wonderful sunsets. The walk to the private beach easy - the beach extremely private and a bit different everyday. There are many lovely walks nearby and within the Spring Point area as well. The fish markets in Menemsha offered great seafood - cooked and fresh and is only a short drive. We also stumbled upon the Chillmark Flea Market which was fun to walk around. Opportunities for great lobster rolls through local churches exist throughout the week. If you need some groceries, Cronig's worked well. You truly feel away from it all here. If you are looking more for shopping, restaurants, people watching, this might not be the place for you. This place truly represents the Up Island experience! Working with the owner was a pleasure - very organized and responsive. This place is a gem!"
    • Stayed August 2016
    • Submitted August 31, 2016
    • Source VRBO
    View this listing