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Chilmark: Houses, Cottages & More (1,673)

  • 1 - 50 of 1,673
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
        2 Reviews
          • 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
                      4
                        • 3 BR
                        • 2 BA
                        • Sleeps 6
                        3
                          • 7 BR
                          • 6 BA
                          • Sleeps 18
                            • 4 BR
                            • 3 BA
                            • Sleeps 12
                            5
                              • 4 BR
                              • 4 BA
                              • 1 HF BA
                              • Sleeps 8
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                7
                                  • 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 5
                                        5
                                          • 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
                                                • 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
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      1 Review
                                                        • 6 BR
                                                        • 2 BA
                                                        • Sleeps 12
                                                        7
                                                          • 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
                                                                      • 5 BR
                                                                      • 3 BA
                                                                      • Sleeps 10
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 5
                                                                        5
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          3
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                              • 5 BR
                                                                              • 4 BA
                                                                              • Sleeps 12
                                                                              1 Review
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                    • 5 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 10
                                                                                    6
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 8
                                                                                      7
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 8
                                                                                        9
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 8
                                                                                          6
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 7
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 5
                                                                                              1 Review
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 6
                                                                                                4
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                    • 4 BR
                                                                                                    • 1 BA
                                                                                                    • 2 HF BA
                                                                                                    • Sleeps 10
                                                                                                    • 1 - 50 of 1,673
                                                                                                     

                                                                                                    Recent Chilmark Reviews

                                                                                                    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

                                                                                                    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

                                                                                                    Lovely home in spectacular, secluded location

                                                                                                    5 of 5
                                                                                                    This review is late in coming but my memories of this magical property are still fresh because I've thought about it so often since. I'll start with what was my biggest criterion: the location. The house is nestled in the Menemsha Hills Reservation, which is my favorite part of Martha's Vineyard, which in turn is my favorite place in the world (and I've explored nearly all of the vineyard, including almost the entire coastline). Menemsha Hills combines staggering natural beauty of great variety (panoramic vantage points, lush forest, gorgeous beaches) with a surprising but welcome lack of people. Even at the height of the season, one rarely sees more than two or three other people in this vast reservation. I've never found anyplace more beautiful, anywhere. Aside from MHR, the house is located near all the best parts of the island. It's close enough to South Shore beaches that you can actually hear the crashing waves on windless nights, very near to Menemsha village if you desire a touch of civilization, and also near Aquinnah and the phenomenal beaches there. The house itself is the most secluded I've stayed at on the island. You can neither see nor hear any neighbors, or any signs of humanity at all. Well, except for the twinkling lights of the Elizabeth islands and the mainland beyond. That's right, the house is at such a high elevation that you can actually see over the Elizabeths. The views are exceptional from the deck, all the living areas, and even some of the bedrooms. And entire house is extremely comfortable, roomy and tranquil. I was there alone, but I'd imagine it could accommodate a large group comfortably. The bed in the master is among the most comfortable I've ever slept on. Oh, and it has heat. I didn't think this would be necessary, and usually, at the time of year I visited, it wouldn't be, but I happened to hit a stretch of severe weather (downpours every day for a solid week, very unusual) which brought nightime temps into the upper 40s. So the heat was a godsend. The owner was a pleasure to work with - very responsive and helpful. All in all, a great house in a spectacular location. Stay here if you can.
                                                                                                    • Submitted: Aug 20, 2016
                                                                                                    • Stayed: Sep 2015