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Chilmark: Houses, Cottages & More (900+)

  • 1 - 50 of 900+
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 8
    10
      • 4 BR
      • 4 BA
      • Sleeps 8
      12
        • 4 BR
        • 3 BA
        • Sleeps 8
        10
          • 3 BR
          • 2 BA
          • Sleeps 6
          4
            • 3 BR
            • 1 BA
            • Sleeps 8
            4
              • 4 BR
              • 2 BA
              • Sleeps 7
              5
                • 4 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 9
                3
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                  4
                    • 4 BR
                    • 1 BA
                    • 1 HF BA
                    • Sleeps 6
                    5
                      • 2 BR
                      • 2 BA
                      • Sleeps 4
                      1 Review
                        • 7 BR
                        • 6 BA
                        • Sleeps 18
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          7
                            • 4 BR
                            • 3 BA
                            • Sleeps 12
                            5
                              • 4 BR
                              • 4 BA
                              • 1 HF BA
                              • Sleeps 8
                                • 4 BR
                                • 2 BA
                                • Sleeps 7
                                5
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 2
                                  6
                                    • 3 BR
                                    • 2 BA
                                    • 1 HF BA
                                    • Sleeps 7
                                    3
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 10
                                      2 Reviews
                                        • 5 BR
                                        • 3 BA
                                        • 1 HF BA
                                        • Sleeps 10
                                        5
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 5
                                          6
                                            • 5 BR
                                            • 2 BA
                                            • 2 HF BA
                                            • Sleeps 12
                                              • 5 BR
                                              • 3 BA
                                              • 1 HF BA
                                              • Sleeps 10
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                5
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  5
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    8
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      1 Review
                                                        • 5 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                          • 5 BR
                                                          • Sleeps 11
                                                          4
                                                            • 3 BR
                                                            • 1 BA
                                                            • 1 HF BA
                                                            • Sleeps 6
                                                            2 Reviews
                                                              • 5 BR
                                                              • 4 BA
                                                              • 1 HF BA
                                                              • Sleeps 8
                                                                • 4 BR
                                                                • 3 BA
                                                                • 1 HF BA
                                                                • Sleeps 8
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • 2 HF BA
                                                                  • Sleeps 10
                                                                  2 Reviews
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 7
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      9
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 5
                                                                        5
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          3
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 8
                                                                            6
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                                • 5 BR
                                                                                • 4 BA
                                                                                • Sleeps 12
                                                                                1 Review
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 8
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 8
                                                                                      2 Reviews
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 6
                                                                                        4
                                                                                          • 5 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 10
                                                                                          8
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                            1 Review
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                                • 3 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                2 Reviews
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 8
                                                                                                  7
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8
                                                                                                    • 1 - 50 of 900+
                                                                                                     

                                                                                                    Recent Chilmark Reviews

                                                                                                    Amazing location, excellent accommodations, wonderful service!

                                                                                                    5 of 5
                                                                                                    This was our third year doing a week-long vacation on the Vineyard and have to say it was the best! The house is set in the middle of the woods only a short drive/walk to the best beaches on the island, namely Lucy Vincent. Our first day there, we returned from the beach and saw a deer right in the front "yard" while eating dinner. How cool is that! The cottage had everything we needed for a great week- cooking supplies, linens, beach chairs, etc. It was very clean. What I loved most about the house was how well-built and high-quality it was. The screened-in porch, for example, has a screen below the deck floor, something most people don't think of, but made all the difference during a pretty buggy time of year. The garage door idea is quirky but after a week there I want one myself! Having that cool breeze circulate through the house is so refreshing after a hot day at the beach. We will be back next year for sure!
                                                                                                    • Submitted: Sep 26, 2016
                                                                                                    • Stayed: Sep 2016

                                                                                                    Picture Perfect Rental

                                                                                                    5 of 5
                                                                                                    Our experience renting this cottage was nothing short of perfect. The views from this property are truly gorgeous, and we spent so much time simply sitting on the deck enjoying coffee and breakfast (from the General Store!) or reading in the afternoon. The beautiful landscaping, wildlife (deer, birds, butterfly, etc), water views, and serenity can not be beat. The cottage was very comfortable for our group of 5. I am 8 months pregnant here with my husband, my older parents, and our 12 year old son. The downstairs is handicap accessible, complete with roll in shower/bathroom. One caveat: the stairs to the second floor are steep; I would consider bringing a baby gate and watching closely if traveling with small children. The house was FULLY equipped with everything we might need; in fact, it was better stocked than most rentals we have encountered. Trash bags, toilet paper, every kitchen appliance you might need, games, books, abundance of towels, hand soap...you name it, they have thoughtfully provided it. There is a small TV in the living room and a DVD player which we enjoyed in the evening watching a family movie. There is wifi throughout the house, though I am not sure about streaming speed - we didn't really test it, and brought DVDs with us. The house had fans in the rooms, but the open windows caught wonderful breezes in the evening and we were comfortable without AC. The house was spotlessly clean; no beachy mildew smells here! The location is not to be beat. Very close to the General Store, Lucy Vincent, Squibnocket, Menemsha, etc. We also had access to an incredible private beach accessible by key a little further down from LV. We were the only people there when we went, and it was spectacular. The cottage is next to the main house, and the family who owns it is incredibly kind and generous. We felt lucky to rent their home. They were very responsive to my (numerous!!!) questions and made us feel so welcome in renting their home. We just learned it is booked up for all of next August and are devastated as we would return in a heartbeat. We feel so fortunate to have spent a week at Lovey's!
                                                                                                    • Submitted: Aug 29, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    Quiet, private retreat with beautiful views; well-appointed, spacious house

                                                                                                    4 of 5
                                                                                                    The house has a great deck with a beautiful view and a nice open flow and living room/dining room. It's set on a very quiet and secluded piece of property with no background noise or direct neighbors. The owner's artwork collection is impressive and adds an unexpected visual dimension to your stay. The kitchen is very open and well-appointed with everything one could need--very conducive to family cooking. It was helpful to have DirecTV, as well as a great sound system, though the wifi and cell service were spotty and weak (probably fault of the services and beyond the control of the owner). The private beach is a nice bonus, but you probably won't use it as your primary beach, as it's a 25 minute hike and a very rocky beach. The back deck with grill and coi pond is a relaxing retreat, too. Overall, we had a lovely stay and would definitely consider this house for future Vineyard visits.
                                                                                                    • Submitted: Aug 28, 2016
                                                                                                    • Stayed: Aug 2016