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 svg-report-flag
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!

Vacation Rentals in Pittsfield, Massachusetts (407)

  • 1 - 50 of 407
Additional fees apply. Taxes may be added.
    • 1 BR
    • 1 BA
    • Sleeps 4
    House #310035vb
      • 3 BR
      • 1 BA
      • Sleeps 8
      House #469617vb
        • 3 BR
        • 2 BA
        • Sleeps 12
        House #420727vb
          • 3 BR
          • 3 BA
          • Sleeps 8
          Condo #878199vb
            • 5 BR
            • 3 BA
            • 2 HF BA
            • Sleeps 9
            Estate #802737vb
              • 2 BR
              • 1 BA
              • Sleeps 7
              Cottage #310698
                • 3 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 9
                Condo #595232vb
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  Apartment #133082
                    • 3 BR
                    • 1 BA
                    • Sleeps 6
                    Cottage #203288vb
                      • 5 BR
                      • 3 BA
                      • Sleeps 8
                      Cottage #425380vb
                        • 3 BR
                        • 2 BA
                        • Sleeps 7
                        House #344576vb
                          • 4 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 10
                          Townhome #4320036
                            • 7 BR
                            • 3 BA
                            • Sleeps 18
                            House #251195vb
                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              Apartment #615402vb
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Cottage #4231093
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Apartment #129461vb
                                    • 5 BR
                                    • 3 BA
                                    • Sleeps 8
                                    House #4160350
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 6
                                      Cottage #300900
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 3
                                        House #135474vb
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 8
                                          House #585864vb
                                            • 3 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 6
                                            House #693973vb
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 8
                                              Condo #907348vb
                                                • 5 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 9
                                                House #923513vb
                                                  • 4 BR
                                                  • 3 BA
                                                  • Sleeps 9
                                                  House #174313
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    Condo #4281302
                                                      • 2 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 4
                                                      House #3002071
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Condo #651723vb
                                                          • 5 BR
                                                          • 3 BA
                                                          • 2 HF BA
                                                          • Sleeps 12
                                                          House #679329vb
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            Condo #3815326
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              House #3731177
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                Condo #786429vb
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  Condo #575909vb
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 7
                                                                    House #700267vb
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      Condo #650023vb
                                                                        • 6 BR
                                                                        • 5 BA
                                                                        • Sleeps 20
                                                                        Estate #4258796
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          House #905333vb
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            Cottage #554803vb
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              Condo #3952850
                                                                                • 10 BR
                                                                                • 9 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 17
                                                                                Estate #4174661
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Townhome #3498317
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Cottage #962761
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 5
                                                                                      House #122780
                                                                                        • 5 BR
                                                                                        • 5 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 14
                                                                                        Chalet #923721
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 5
                                                                                          Condo #711064vb
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 9
                                                                                            House #404919vb
                                                                                              • 3 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              House #752883vb
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 8
                                                                                                House #3595415
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 7
                                                                                                  House #286733vb
                                                                                                    • 4 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 10
                                                                                                    Barn #346642vb
                                                                                                    • 1 - 50 of 407