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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.

  • Showing 1-50 of 300+
Additional service fee may apply.
    Exceptional! 5.0/5
    (10 reviews)
    avg/night
    • 4 BR
    • 4 BA
    • Sleeps 8
    House #704051vb
    10
    Viewed 11 times in the last 48 hours
      Exceptional! 5.0/5
      (8 reviews)
      avg/night
      • 4 BR
      • 2 BA
      • Separate Toilet
      • Sleeps 8
      House #679747vb
      8
      Viewed 22 times in the last 48 hours
        avg/night
        • 4 BR
        • 3 BA
        • Separate Toilets
        • Sleeps 10
        House #837823vb
        3
        Viewed 18 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 9 times in the last 48 hours
            • 3 BR
            • 2 BA
            • Sleeps 8
            House #663482vb
            6
              Wonderful! 4.8/5
              (8 reviews)
              avg/night
              • 5 BR
              • 3 BA
              • Sleeps 10
              House #980094
              8
                Exceptional! 5.0/5
                (5 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 6
                House #840127vb
                5
                Viewed 6 times in the last 48 hours
                  Wonderful! 4.9/5
                  (10 reviews)
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                  • Studio
                  • Sleeps 2
                  Studio #165500
                  10
                  Viewed 8 times in the last 48 hours
                    Wonderful! 4.9/5
                    (14 reviews)
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                    • 4 BR
                    • 4 BA
                    • Sleeps 8
                    Estate #559364vb
                    14
                    Viewed 44 times in the last 48 hours
                      • 2 BR
                      • 2 BA
                      • Sleeps 6
                      Cottage #580958vb
                      3
                        Exceptional! 5.0/5
                        (6 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        Apartment #3802195
                        6
                        Viewed 24 times in the last 48 hours
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                          • 2 BR
                          • 2 BA
                          • Sleeps 4
                          Cottage #4231281
                          3
                          Viewed 8 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 14 times in the last 48 hours
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                              • 3 BR
                              • 2 BA
                              • Sleeps 8
                              House #4165995
                              Viewed 14 times in the last 48 hours
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Separate Toilet
                                • Sleeps 7
                                House #3708573
                                3
                                Viewed 12 times in the last 48 hours
                                  • 5 BR
                                  • 3 BA
                                  • Sleeps 8
                                  House #597355vb
                                  Viewed 5 times in the last 48 hours
                                    Excellent! 4.7/5
                                    (6 reviews)
                                    avg/night
                                    • 3 BR
                                    • 1 BA
                                    • Sleeps 8
                                    House #568907vb
                                    6
                                    Viewed 24 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (5 reviews)
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                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 7
                                      House #720739vb
                                      5
                                      Viewed 10 times in the last 48 hours
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                                        • 4 BR
                                        • 2 BA
                                        • Sleeps 11
                                        House #911333vb
                                        Viewed 119 times in the last 48 hours
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                                          • 5 BR
                                          • 2 BA
                                          • Sleeps 10
                                          House #415177vb
                                          Viewed 7 times in the last 48 hours
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 7
                                            House #454191vb
                                            1
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 8
                                              House #3549672
                                              4
                                              Viewed 8 times in the last 48 hours
                                                • 3 BR
                                                • 2 BA
                                                • Separate Toilet
                                                • Sleeps 8
                                                House #505692vb
                                                7
                                                  avg/night
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 5
                                                  Cottage #874121vb
                                                  1
                                                  Viewed 5 times in the last 48 hours
                                                    • 3 BR
                                                    • 2 BA
                                                    • Separate Toilet
                                                    • Sleeps 4
                                                    House #223892
                                                    Viewed 12 times in the last 48 hours
                                                      Good! 3.8/5
                                                      (8 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                      Cottage #302374vb
                                                      8
                                                      Viewed 98 times in the last 48 hours
                                                        • 4 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        House #843514vb
                                                          Exceptional! 5.0/5
                                                          (5 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 5
                                                          Cottage #508322vb
                                                          5
                                                          Viewed 12 times in the last 48 hours
                                                            • 4 BR
                                                            • 5 BA
                                                            • Sleeps 12
                                                            House #883157vb
                                                            1
                                                            Viewed 45 times in the last 48 hours
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                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 7
                                                              House #846409vb
                                                              Viewed 7 times in the last 48 hours
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                                                                • 3 BR
                                                                • 2 BA
                                                                • Separate Toilet
                                                                • Sleeps 7
                                                                House #81484vb
                                                                Viewed 9 times in the last 48 hours
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                                                                  • 3 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  Cottage #472272vb
                                                                  4
                                                                  Viewed 8 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (5 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    House #472487vb
                                                                    5
                                                                    Viewed 15 times in the last 48 hours
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      Cottage #3779593
                                                                      1
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                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        House #3942407
                                                                        1
                                                                        Viewed 13 times in the last 48 hours
                                                                          • 4 BR
                                                                          • 1 BA
                                                                          • Separate Toilets
                                                                          • Sleeps 10
                                                                          Cottage #712092vb
                                                                            • 5 BR
                                                                            • 3 BA
                                                                            • Sleeps 9
                                                                            Cottage #3959151
                                                                              avg/night
                                                                              • 5 BR
                                                                              • 3 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 14
                                                                              Estate #813704vb
                                                                              1
                                                                              Viewed 6 times in the last 48 hours
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                House #859100vb
                                                                                3
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                                                                                  • 6 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 12
                                                                                  House #858582vb
                                                                                  Viewed 16 times in the last 48 hours
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                                                                                    • 5 BR
                                                                                    • 4 BA
                                                                                    • Sleeps 12
                                                                                    House #733046vb
                                                                                    1
                                                                                    Viewed 30 times in the last 48 hours
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      House #753236vb
                                                                                      4
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                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        House #106032
                                                                                        Viewed 5 times in the last 48 hours
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 8
                                                                                          House #182266
                                                                                          2
                                                                                            • 4 BR
                                                                                            • 1 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 8
                                                                                            House #761276vb
                                                                                            1
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 10
                                                                                              House #845741vb
                                                                                                Exceptional! 5.0/5
                                                                                                (9 reviews)
                                                                                                View details for price
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 8
                                                                                                House #599182vb
                                                                                                9
                                                                                                  Exceptional! 5.0/5
                                                                                                  (8 reviews)
                                                                                                  avg/night
                                                                                                  • 5 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 10
                                                                                                  House #283441vb
                                                                                                  8
                                                                                                  Viewed 8 times in the last 48 hours
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 6
                                                                                                    House #151143
                                                                                                    4
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