check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chilmark: Houses, Cottages & More (1,674)

  • 1 - 50 of 1,674
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
                            • 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
                                                                                                    7
                                                                                                    • 1 - 50 of 1,674
                                                                                                     

                                                                                                    Recent Chilmark Reviews

                                                                                                    Marvelous!

                                                                                                    5 of 5
                                                                                                    My daughter and I spent the second week of August, 2016 at Susanna's wonderful home. It's situated up Island, atop Prospect Hill in Chilmark with wonderful views of Vineyard Sound from the front deck. If seclusion, privacy and quick access to the beautiful beaches, Brickyard (a short walk from the house), Lucy Vincent, Squibnocket, Menemsha, Aquinnah and Gay Head are your objectives..well, this is the place! It's not just my opinion.. The POTUS and his family were our neighbors for the week. The Secret Service has it down and the security was friendly and welcoming, not disruptive at all. Chelsea and I enjoyed meeting Susanna. She's an artist, a Vineyard historian, a birder and responsive to your vacation needs. BTW, Everything in the house works! No surprises... David McLarnon
                                                                                                    • Submitted: Aug 26, 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