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Chilmark: Houses, Cottages & More (1,678)

  • 1 - 50 of 1,678
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
                • 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 8
                    1 Review
                      • 4 BR
                      • 1 BA
                      • 1 HF BA
                      • Sleeps 6
                      4
                        • 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
                                  3
                                    • 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
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                5
                                                  • 4 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  1 Review
                                                    • 5 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                      • 6 BR
                                                      • 2 BA
                                                      • Sleeps 12
                                                      7
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        10
                                                          • 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
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  6
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • 2 HF BA
                                                                    • Sleeps 10
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 4
                                                                        • 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
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 6
                                                                                            4
                                                                                              • 5 BR
                                                                                              • 4 BA
                                                                                              • Sleeps 12
                                                                                              1 Review
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 8
                                                                                                6
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 7
                                                                                                  • 1 - 50 of 1,678
                                                                                                   

                                                                                                  Recent Chilmark Reviews

                                                                                                  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

                                                                                                  You can not find a better place!!

                                                                                                  5 of 5
                                                                                                  This is the best hidden GEM on the island. The property is just gorgeous, if you are looking for peace and quiet this is your place. The apartment is spotless!! Everything is new and clean and it looks much larger then 750sq. The owner Richard is the definition of a perfect gentleman. He has been in the hospitality business for 20 years and he passes it right on to make sure your stay is perfect!, When he would leave early in the morning he would do everything possible to avoid waking us up at 630 am. Staying above his garage in consideration he would leave his car in the driveway to avoid and noise. His dog Tucker is the most gentle and lovable dog. I rarely ever write a review and I hope I'm not giving it away for next year but if you have a chance to stay here you will have no regrets. Everything you are looking for is in the beautiful carrage house.
                                                                                                  • Submitted: Jul 24, 2016
                                                                                                  • Stayed: Jul 2016