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Make a self-catering beach house or holiday rental in Chilmark, Martha’s Vineyard, USA your home away from home

The town of Chilmark is in the southwest corner of Martha’s Vineyard, an exclusive island off the coast of Massachusetts. It is famous for its holiday homes, beautiful beaches and unspoilt natural reserves.

Things to Do in Chilmark, Martha’s Vineyard

Most visitors rent Cape Cod holiday homes to relax and chill out but there is plenty to do for those who are more active. The island has several beautiful sandy beaches for swimming, watersports, building sandcastles or sunbathing with a good book. There are scenic cycle trails and quiet roads which make cycling around the area a pleasure, visiting small towns along the way. West Chop Woods has miles of hiking trails or visitors can hire a boat and go fishing around the coast of Menemsha, just north of their Chilmark holiday home. Scenic cruises and whale watching trips in the spring are always popular activities. Golfers can enjoy playing at the Mink Meadow Golf Course near Vineyard Haven or at the Farm Neck Golf Course at Oak Bluffs.

Places to Visit Around Chilmark, Martha’s Vineyard

West Tisbury is one of the prettiest villages on Martha’s Vineyard with a downtown area featuring Alley’s General Store which claims to sell almost everything. Browse the local artworks nearby in the Field Gallery and pick up a souvenir of your stay. Edgartown is the oldest English settlement in the area with characterful captain’s houses and New England-style architecture which dates back to the island’s whaling days. Vincent House is the oldest residence on the island, built in 1672 and filled with period furniture. Alternatively, take a trip by ferry to nearby Chappaquiddick Island which was joined to Martha’s Vineyard until a storm in 2007 washed away the causeway.

Weather in Chilmark, MA

Holiday rentals in Chilmark generally have warm sunny days in the summer and cold winters with some snow. This is mainly a summer vacation resort when temperatures reach a pleasant 79°F (26°C) in July and August. From November to March temperatures regularly drop below freezing overnight. The area has moderate rainfall throughout the year.

Travel to Chilmark, Martha’s Vineyard

The nearest airport to your holiday rental in Chilmark is Boston Logan International (BOS) Airport which is 102 miles away. It is easy to pick up a hire car and drive to Martha’s Vineyard along the I-93. Boston Airport is a key airport for JetBlue Airways and a major operating destination for Delta and US Airways. It has frequent flights from most American cities as well as from Canada and Europe. There is a small regional airport on Martha’s Vineyard (MVY) which has connecting flights to Boston, Providence and New Bedford airports. It is just 9 miles from Chilmark holiday homes.

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  • 1 - 50 of 300+
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    Exceptional! 5.0/5
    (10 reviews)
    avg/night
    • 4 BR
    • 4 BA
    • Sleeps 8
    House #704051vb
    10
    Viewed 10 times in the last 48 hours
      Exceptional! 5.0/5
      (5 reviews)
      avg/night
      • 4 BR
      • 1 BA
      • Separate Toilet
      • Sleeps 6
      House #3932081
      5
      Viewed 13 times in the last 48 hours
        Exceptional! 5.0/5
        (5 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 6
        House #840127vb
        5
        Viewed 21 times in the last 48 hours
          Wonderful! 4.8/5
          (5 reviews)
          avg/night
          • 4 BR
          • 2 BA
          • Sleeps 7
          House #720739vb
          5
          Viewed 13 times in the last 48 hours
            • 4 BR
            • 3 BA
            • Separate Toilets
            • Sleeps 10
            House #837823vb
            2 Reviews
              Exceptional! 5.0/5
              (7 reviews)
              avg/night
              • 4 BR
              • 2 BA
              • Separate Toilet
              • Sleeps 8
              House #679747vb
              7
              Viewed 8 times in the last 48 hours
                Wonderful! 4.8/5
                (8 reviews)
                avg/night
                • 5 BR
                • 3 BA
                • Sleeps 10
                House #980094
                8
                Viewed 12 times in the last 48 hours
                  • 4 BR
                  • 5 BA
                  • Sleeps 12
                  House #883157vb
                  1 Review
                  Viewed 21 times in the last 48 hours
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    House #4165995
                    Viewed 5 times in the last 48 hours
                      avg/night
                      • 4 BR
                      • 2 BA
                      • Sleeps 11
                      House #911333vb
                      Viewed 20 times in the last 48 hours
                        Exceptional! 5.0/5
                        (12 reviews)
                        avg/night
                        • 3 BR
                        • 1 BA
                        • Separate Toilet
                        • Sleeps 8
                        House #371811vb
                        12
                        Viewed 8 times in the last 48 hours
                          Wonderful! 4.9/5
                          (13 reviews)
                          avg/night
                          • 4 BR
                          • 4 BA
                          • Sleeps 8
                          Estate #559364vb
                          13
                          Viewed 12 times in the last 48 hours
                            avg/night
                            • 2 BR
                            • 2 BA
                            • Sleeps 4
                            Cottage #4231281
                            3
                            Viewed 11 times in the last 48 hours
                              avg/night
                              • 4 BR
                              • 3 BA
                              • Sleeps 8
                              House #182266
                              2 Reviews
                              Viewed 8 times in the last 48 hours
                                avg/night
                                • 4 BR
                                • 2 BA
                                • Sleeps 8
                                House #106032
                                Viewed 5 times in the last 48 hours
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 7
                                  House #454191vb
                                  1 Review
                                  Viewed 8 times in the last 48 hours
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 6
                                    House #753236vb
                                    4
                                    Viewed 27 times in the last 48 hours
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 5
                                      Cottage #874121vb
                                      1 Review
                                      Viewed 5 times in the last 48 hours
                                        avg/night
                                        • 5 BR
                                        • 4 BA
                                        • Sleeps 12
                                        House #733046vb
                                        1 Review
                                        Viewed 8 times in the last 48 hours
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          Cottage #580958vb
                                          3
                                          Viewed 6 times in the last 48 hours
                                            • 4 BR
                                            • 1 BA
                                            • Separate Toilet
                                            • Sleeps 8
                                            House #761276vb
                                            1 Review
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • Separate Toilet
                                              • Sleeps 7
                                              House #3708573
                                              3
                                              Viewed 7 times in the last 48 hours
                                                Excellent! 4.7/5
                                                (6 reviews)
                                                avg/night
                                                • 3 BR
                                                • 1 BA
                                                • Sleeps 8
                                                House #568907vb
                                                6
                                                Viewed 8 times in the last 48 hours
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  House #3942407
                                                  1 Review
                                                    • 5 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    House #597355vb
                                                    Viewed 6 times in the last 48 hours
                                                      avg/night
                                                      • 5 BR
                                                      • 3 BA
                                                      • Sleeps 10
                                                      House #202640vb
                                                      Viewed 27 times in the last 48 hours
                                                        • 3 BR
                                                        • 1 BA
                                                        • Sleeps 6
                                                        Cottage #472272vb
                                                        2 Reviews
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          House #681481vb
                                                          2 Reviews
                                                          Viewed 10 times in the last 48 hours
                                                            • 5 BR
                                                            • 3 BA
                                                            • Sleeps 9
                                                            Cottage #3959151
                                                              Excellent! 4.5/5
                                                              (6 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              House #663482vb
                                                              6
                                                              Viewed 10 times in the last 48 hours
                                                                Good! 3.8/5
                                                                (8 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                Cottage #302374vb
                                                                8
                                                                Viewed 29 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (13 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 7
                                                                  House #347615vb
                                                                  13
                                                                  Viewed 5 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (5 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    House #472487vb
                                                                    5
                                                                    Viewed 8 times in the last 48 hours
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 8
                                                                      House #599182vb
                                                                      9
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Separate Toilet
                                                                        • Sleeps 6
                                                                        House #151143
                                                                        4
                                                                          avg/night
                                                                          • 5 BR
                                                                          • 2 BA
                                                                          • Sleeps 10
                                                                          House #415177vb
                                                                          Viewed 14 times in the last 48 hours
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            House #843514vb
                                                                              • 4 BR
                                                                              • 3 BA
                                                                              • Sleeps 8
                                                                              House #738870vb
                                                                              Viewed 7 times in the last 48 hours
                                                                                • 4 BR
                                                                                • 1 BA
                                                                                • Separate Toilets
                                                                                • Sleeps 10
                                                                                Cottage #712092vb
                                                                                  Exceptional! 5.0/5
                                                                                  (7 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 8
                                                                                  House #505692vb
                                                                                  7
                                                                                  Viewed 9 times in the last 48 hours
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    House #859100vb
                                                                                    3
                                                                                      • 3 BR
                                                                                      • 3 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 8
                                                                                      House #688443vb
                                                                                        Exceptional! 5.0/5
                                                                                        (9 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 4 BA
                                                                                        • Separate Toilet
                                                                                        • Sleeps 8
                                                                                        House #507862vb
                                                                                        9
                                                                                        Viewed 9 times in the last 48 hours
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 9
                                                                                          House #277295
                                                                                          3
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 4
                                                                                            House #715165vb
                                                                                            3
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Separate Toilets
                                                                                              • Sleeps 8
                                                                                              House #329587vb
                                                                                              21
                                                                                                Exceptional! 5.0/5
                                                                                                (5 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 12
                                                                                                House #136112
                                                                                                5
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  House #112239
                                                                                                  Viewed 16 times in the last 48 hours
                                                                                                  • 1 - 50 of 300+