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Chilmark: Houses, Cottages & More (1,675)

  • 1 - 50 of 1,675
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 8
    9
      • 4 BR
      • 4 BA
      • Sleeps 8
      12
        • 3 BR
        • 2 BA
        • Sleeps 6
        3
          • 4 BR
          • 3 BA
          • Sleeps 8
          10
            • 3 BR
            • 1 BA
            • Sleeps 8
            4
              • 4 BR
              • 2 BA
              • Sleeps 7
              4
                • 3 BR
                • 2 BA
                • Sleeps 6
                4
                  • 4 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 9
                  3
                    • 4 BR
                    • 1 BA
                    • 1 HF BA
                    • Sleeps 8
                    1 Review
                      • 4 BR
                      • 1 BA
                      • 1 HF BA
                      • Sleeps 6
                      5
                        • 3 BR
                        • 2 BA
                        • Sleeps 6
                        3
                          • 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
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 6
                                    5
                                      • 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
                                            • 5 BR
                                            • 3 BA
                                            • 1 HF BA
                                            • Sleeps 10
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 5
                                              5
                                                • 5 BR
                                                • 2 BA
                                                • 2 HF BA
                                                • Sleeps 12
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  6
                                                    • 4 BR
                                                    • 3 BA
                                                    • 2 HF BA
                                                    • Sleeps 10
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                        • 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
                                                                    • 1 BR
                                                                    • Sleeps 2
                                                                    10
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 8
                                                                        9
                                                                          • 5 BR
                                                                          • 3 BA
                                                                          • Sleeps 10
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 5
                                                                            5
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 5
                                                                              1 Review
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                3
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 8
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 8
                                                                                        6
                                                                                          • 5 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 12
                                                                                          1 Review
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 7
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 6
                                                                                              4
                                                                                                • 5 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 10
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
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                                                                                                    • 1 - 50 of 1,675
                                                                                                     

                                                                                                    Recent Chilmark Reviews

                                                                                                    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

                                                                                                    Take me away to my Happy Place

                                                                                                    5 of 5
                                                                                                    Exceptional Property. We’ve long been enjoying our time at this property as repeat summer guests. A much-loved family tradition! We take the big main house as well as the smaller guest house (Lovey’s Cottage), which allows our 3-generation family a lot of flexibility. Here’s what we enjoy about the Tower House, specifically: - The house is beautifully kept – well-furnished and maintained. And we love being part of its special history! - Such a spacious feel – and lots of light -- in all the rooms (comfortable beds in the bedrooms!) - The kitchen’s big and sunny, very inviting. And the huge back hang-out deck…sublime. - Fabulous view: all the way to Menemsha fishing village, and past the islands beyond. - The property’s big, private grounds. Great for kids running around, exploring, and just having fun. - Having Lovey’s Cottage guest house on the property, which we also really enjoy renting, for smaller family groups, and our guests. - The 2 private beaches are a big deal for us… Lovey’s beach (fantastic for small kids), and Hancock beach (wow, no crowds!). - 3 other public beaches only minutes from the house: Squibnocket, Lucy Vincent, and Aquinnah. - Wonderful restaurants within a 5-10 minute drive: Outermost, Chilmark Tavern, HomePort, Beach Plum. - A lot of nice island walking trails in close range of the house. - Grocery stores, gas, library, community center (with kids’ programs), farm stands and fish markets all in Chilmark and nearby Menemsha.. These are some of the best weeks of every summer for us.
                                                                                                    • Submitted: Aug 22, 2016
                                                                                                    • Stayed: Jun 2016

                                                                                                    So Lovely!

                                                                                                    5 of 5
                                                                                                    Our Sweet Spot. Here’s what we enjoy about Lovey’s Cottage, specifically: - Its open plan first-floor rooms: so the small house reads big. And upstairs, it sleeps up to six. - It’s always kept clean, neat, and very comfortably furnished. Linens, towels are all stocked too. - Its kitchen is well-equipped. Its library holds good books/games for kids (of many ages). - The view is amazing: all the way across the pond to Menemsha fishing village, and out over the Sound. - The sunny deck is where we spend a lot of time, hanging out, and enjoying the fabulous view. - The 2 private beaches are a big deal for us… Lovey’s beach (fantastic for small kids), and Hancock beach (bliss, no crowds!). - Plus 3 other public beaches only minutes from the house: Squibnocket, Lucy Vincent, and Aquinnah. - Wonderful restaurants within a 5-10 minute drive: Outermost, Chilmark Tavern, HomePort, Beach Plum. - A lot of nice island walking trails within close range of the house. - Grocery stores, gas, library, community center (with kids’ programs), farm stands and fish markets all in Chilmark and nearby Menemsha. Lovey’s Cottage is perfect for our smaller family units, and our guests, but with privacy from the Tower House, on the same property. Coming back here year after year – these are some of the best weeks of every summer for us!
                                                                                                    • Submitted: Aug 22, 2016
                                                                                                    • Stayed: Jun 2016