check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar
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!

Chappaquiddick: Vacation Rentals (855)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    • 3 BR
    • 2 BA
    • Sleeps 5
      • 3 BR
      • 2 BA
      • Sleeps 7
      1 Review
        • 2 BR
        • 2 BA
        • Sleeps 4
          • 7 BR
          • 2 BA
          • 2 HF BA
          • Sleeps 12
          2 Reviews
            • 3 BR
            • 1 BA
            • 1 HF BA
            • Sleeps 8
            2 Reviews
              • 2 BR
              • 1 BA
              • 1 HF BA
              • Sleeps 5
              1 Review
                • 3 BR
                • 2 BA
                • Sleeps 8
                  • 3 BR
                  • 1 BA
                  • 1 HF BA
                  • Sleeps 6
                  2 Reviews
                    • 5 BR
                    • 4 BA
                    • Sleeps 9
                    1 Review
                      • 4 BR
                      • 2 BA
                      • 2 HF BA
                      • Sleeps 8
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          1 Review
                            Excellent! 4.6/5
                            (9 reviews)
                            avg/night
                            • 4 BR
                            • 2 BA
                            • Sleeps 8
                            9
                              • 3 BR
                              • 2 BA
                              • Sleeps 12
                              13
                                • 4 BR
                                • 4 BA
                                • Sleeps 8
                                1 Review
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 2
                                  2 Reviews
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 8
                                    6
                                      Excellent! 4.6/5
                                      (9 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 4
                                      9
                                        Exceptional! 5.0/5
                                        (6 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        6
                                          NEW!
                                          • 3 BR
                                          • Sleeps 9
                                          1 Review
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 6
                                            9
                                              Excellent! 4.3/5
                                              (9 reviews)
                                              View details for price
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              9
                                                NEW!
                                                • 2 BR
                                                • 1 BA
                                                • 1 HF BA
                                                • Sleeps 6
                                                  • 3 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 8
                                                  6
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    30
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      5
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        4
                                                          • 3 BR
                                                          • 1 BA
                                                          • 1 HF BA
                                                          • Sleeps 6
                                                          2 Reviews
                                                            • 5 BR
                                                            • 4 BA
                                                            • Sleeps 10
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                                Exceptional! 5.0/5
                                                                (9 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 3 BA
                                                                • Sleeps 8
                                                                9
                                                                  • 4 BR
                                                                  • 4 BA
                                                                  • Sleeps 10
                                                                  4
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    3
                                                                      Wonderful! 4.9/5
                                                                      (10 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      10
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • Sleeps 6
                                                                        24
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 5
                                                                            Wonderful! 4.8/5
                                                                            (9 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 7
                                                                            9
                                                                              Exceptional! 5.0/5
                                                                              (5 reviews)
                                                                              avg/night
                                                                              • 7 BR
                                                                              • 5 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 14
                                                                              5
                                                                                NEW!
                                                                                • 4 BR
                                                                                • 4 BA
                                                                                • Sleeps 8
                                                                                  NEW!
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                  1 Review
                                                                                    • 4 BR
                                                                                    • 4 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 10
                                                                                    5
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 9
                                                                                      2 Reviews
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 8
                                                                                          NEW!
                                                                                          • 4 BR
                                                                                          • 4 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 8
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 8
                                                                                              • 3 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 7
                                                                                              1 Review
                                                                                                Excellent! 4.4/5
                                                                                                (7 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                7
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  1 Review
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    1 Review
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 9
                                                                                                      3
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Chappaquiddick Reviews

                                                                                                      September getaway

                                                                                                      5 of 5
                                                                                                      This home is a lovely, exceptionally well cared for, well appointed place for a quiet getaway on Chappy. We have traveled to Martha's Vineyard for over 45 years & would not hesitate to say that this is the nicest vacation rental we have ever stayed in.
                                                                                                      • Submitted: Sep 25, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Great place....pleasant stay!

                                                                                                      4 of 5
                                                                                                      We had a great stay at this comfortable cottage. It's a very quiet and private location. Close to Edgartown, the bike path and South Beach. Great access to Wilson's Landing and Katama Bay for kayaking. There were bicycles and kayaks available. John and Kelly were helpful with any questions or needs. We hope to plan another stay in the future.
                                                                                                      • Submitted: Sep 21, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Comfortable home, wonderful stay, lots of history, location is unparalleled

                                                                                                      5 of 5
                                                                                                      Pam Spear's home was wonderful to stay at and she was very easy to work with. It was very comfortable house with plenty of room and easy to entertain in. You absolutely cannot beat the location, which is about a 2 min walk to downtown historic Edgartown. We had a wonderful time over Labor Day weekend and look forward to hopefully staying at this great home again!
                                                                                                      • Submitted: Sep 6, 2016
                                                                                                      • Stayed: Sep 2016