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Pittsfield: Houses, Cottages & More (323)

  • 1 - 50 of 323
Additional fees apply. Taxes may be added.
    • 1 BR
    • 1 BA
    • Sleeps 4
    21
      • 3 BR
      • 1 BA
      • Sleeps 8
      31
        • 3 BR
        • 3 BA
        • Sleeps 8
        1 Review
          • 5 BR
          • 3 BA
          • Sleeps 10
          1 Review
            • 5 BR
            • 3 BA
            • 2 HF BA
            • Sleeps 9
              • 3 BR
              • 2 BA
              • Sleeps 12
              27
                • 2 BR
                • 1 BA
                • Sleeps 7
                3
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  12
                    • 4 BR
                    • 3 BA
                    • 1 HF BA
                    • Sleeps 12
                    3
                      • 3 BR
                      • 1 BA
                      • Sleeps 6
                      12
                        • 3 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 9
                        7
                          • 5 BR
                          • 3 BA
                          • Sleeps 8
                          2 Reviews
                            • 3 BR
                            • 2 BA
                            • Sleeps 7
                            7
                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              4
                                • 7 BR
                                • 3 BA
                                • Sleeps 18
                                22
                                  • 4 BR
                                  • 3 BA
                                  • 1 HF BA
                                  • Sleeps 8
                                    • 3 BR
                                    • 1 BA
                                    • 1 HF BA
                                    • Sleeps 5
                                      • Studio
                                      • 1 BA
                                      • Sleeps 2
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 6
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 4
                                            11
                                              • 5 BR
                                              • 3 BA
                                              • 2 HF BA
                                              • Sleeps 12
                                              3
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                5
                                                  • 5 BR
                                                  • 3 BA
                                                  • Sleeps 10
                                                  2 Reviews
                                                    • 3 BR
                                                    • 2 BA
                                                    • 1 HF BA
                                                    • Sleeps 6
                                                    6
                                                      • 2 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 4
                                                      11
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          3
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 5
                                                            2 Reviews
                                                              • 10 BR
                                                              • 9 BA
                                                              • 1 HF BA
                                                              • Sleeps 17
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                17
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  4
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    7
                                                                      • 3 BR
                                                                      • Sleeps 6
                                                                      4
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 10
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 3
                                                                          27
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              5
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  1 Review
                                                                                    • 3 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 6
                                                                                    2 Reviews
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 9
                                                                                      5
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 9
                                                                                        5
                                                                                          • 4 BR
                                                                                          • 4 BA
                                                                                          • Sleeps 8
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                            4
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 8
                                                                                              6
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 2
                                                                                                  • 5 BR
                                                                                                  • 5 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 10
                                                                                                  1 Review
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 8
                                                                                                      • 1 - 50 of 323
                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      Wonderfully relaxing

                                                                                                      5 of 5
                                                                                                      A beautiful place to spend a few days and get away from it all, but close enough to everything fun and exciting in the Berkeshires! We had a lovely stay!
                                                                                                      • Submitted: Sep 10, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Beautiful country home!

                                                                                                      5 of 5
                                                                                                      We stayed in this home for seven weeks during the summer. It was glorious. The home is beautifully decorated and clearly loved. The owners were easy to reach and very responsive with any and all questions. The location is perfect for easy access to Lenox and Pittsfield and a short drive to Stockbridge and Lee. What a gem!
                                                                                                      • Submitted: Aug 24, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      Great location , downtown Lenox

                                                                                                      4 of 5
                                                                                                      The location of this rental was ideal, in a lovely quiet street just steps from the main part of Lenox. An older building, amenities were sufficient and quite comfortable for a two day stay. Although we did not prepare any meals, there was ample space and basic supplies provided. Wifi and AC worked well, and comfortably slept five. Would definitely stay here again.
                                                                                                      • Submitted: Aug 3, 2016
                                                                                                      • Stayed: Jul 2016