Book a Chilmark Rental for a Perfect Massachusetts Getaway

When you think of a Massachusetts vacation, Martha’s Vineyard probably comes to mind. Chilmark is on the western coast of the island and is often referred to as “up-island” by the locals. It is known for its stone walls, rolling meadows, and one of the best beaches on the island, Lucy Vincent Beach. Chilmark also has the highest property values in the state, which makes a Chilmark rental quite prestigious.

Chilmark Vacation Rentals in a Fishing Village


With Chilmark rentals, it is possible to take in the rustic charm of Menemsha, a small fishing village opening up to the Vineyard Sound. It was in this village that much of the film “Jaws” was shot. Local fishermen and visitors from Chilmark vacation rentals alike take advantage of the well-populated waters. Visitors to a Chilmark rental may charter a fishing boat or visit Dutcher’s Dock for a plethora of fresh fish markets.

Best Beach Offered to Chilmark Rentals


Lucy Vincent Beach is one of the best beaches available to those who stay in Chilmark rentals. It is a private beach, intended for island residents only, but if you have a Chilmark rental, this won’t be a problem as you can get the proper identification issued at the city hall. The popular beach may shock some people who stay in Chilmark vacation rentals as nudity is allowed, so just be advised when you arrive!

With a Chilmark Rental, There’s Plenty to Do


With a Chilmark rental, you don’t have to stay right in town. Martha’s Vineyard is small enough that you can visit each small town on a different day and still enjoy your time at your Chilmark rentals in the evening. There are plenty of antique shops and specialty stores to fill your days after beach bumming and eating! Chilmark vacation rentals allow for a true Massachusetts getaway and are perfect for three-day weekends or a week in the summer.

Increase your search options for Martha's Vineyard lodging in the following areas: vacation rentals in Chappaquiddick, lodging in Edgartown MA, Katama beach homes, Vineyard Haven home rental, or vacation accommodation West Tisbury MA.



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Chilmark: Houses, Cottages & More(180)

180 Results
2 - 7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
#559364vb
(3)
    2 - 7 night minimum stay
    • 3 BR,
    • 1 BA,
    • Sleeps 8
    #568907vb
    (3)
    7 night minimum stay
    • 4 BR,
    • 3 BA,
    • Sleeps 12
    #136112
    (4)
      3 - 7 night minimum stay
      • 3 BR,
      • 3 BA,
      • Sleeps 8
      #231734
      (5)
        7 night minimum stay
        • 3 BR,
        • 2 BA,
        • Sleeps 8
        #942442
          7 night minimum stay
          • 4 BR,
          • 3 BA,
          • Sleeps 8
          #942336
            $2,700 - $4,200
            per week
            7 night minimum stay
            • 2 BR,
            • 1 BA,
            • Sleeps 4
            #942337
              7 night minimum stay
              • 5 BR,
              • 3 BA,
              • Sleeps 8
              #981928
                7 night minimum stay
                • 5 BR,
                • 3 BA,
                • Sleeps 12
                #942400
                  $2,500 - $12,500
                  per week
                  7 night minimum stay
                  • 2 BR,
                  • 1 BA,
                  • Sleeps 4
                  #942260
                    $4,850 - $6,850
                    per week
                    7 night minimum stay
                    • 4 BR,
                    • 2 BA,
                    • Sleeps 8
                    #942381
                      7 night minimum stay
                      • 5 BR,
                      • Sleeps 9
                      #3197978
                        7 night minimum stay
                        • 4 BR,
                        • 3 BA,
                        • Sleeps 8
                        #3489200
                          7 night minimum stay
                          • 5 BR,
                          • 3 BA,
                          • Sleeps 10
                          #3489211
                            7 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 6
                            #372010
                            (5)
                              $4,000 - $7,000
                              per week
                              7 night minimum stay
                              • 4 BR,
                              • 3 BA,
                              • 1 HF BA,
                              • Sleeps 8
                              #3024982
                                7 night minimum stay
                                • 3 BR,
                                • 3 BA,
                                • Sleeps 8
                                #3572496
                                  7 night minimum stay
                                  • 5 BR,
                                  • 3 BA,
                                  • 1 HF BA,
                                  • Sleeps 10
                                  #347308
                                    7 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                    #293733
                                    1 Review
                                      7 night minimum stay
                                      • 5 BR,
                                      • 3 BA,
                                      • 1 HF BA,
                                      • Sleeps 10
                                      #293730
                                      (3)
                                        7 night minimum stay
                                        • 5 BR,
                                        • 3 BA,
                                        • Sleeps 10
                                        #3564258
                                          $1,000 - $12,500
                                          per week
                                          7 night minimum stay
                                          • 2 BR,
                                          • 1 BA,
                                          • Sleeps 4
                                          #3564231
                                            7 night minimum stay
                                            • 4 BR,
                                            • 3 BA,
                                            • Sleeps 10
                                            #3564253
                                              7 night minimum stay
                                              • 4 BR,
                                              • 4 BA,
                                              • 1 HF BA,
                                              • Sleeps 8
                                              #942261
                                                $4,150 - $6,150
                                                per week
                                                7 night minimum stay
                                                • 4 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 10
                                                #942200
                                                  14 night minimum stay
                                                  • 4 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
                                                  #942521
                                                    7 night minimum stay
                                                    • 6 BR,
                                                    • Sleeps 11
                                                    #3489194
                                                      7 night minimum stay
                                                      • 3 BR,
                                                      • 1 HF BA,
                                                      • Sleeps 6
                                                      #3489192
                                                        7 night minimum stay
                                                        • 5 BR,
                                                        • Sleeps 10
                                                        #3489199
                                                          7 night minimum stay
                                                          • 4 BR,
                                                          • 2 BA,
                                                          • Sleeps 8
                                                          #3197982
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