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  • 1 - 22 of 22
Additional fees apply. Taxes may be added.
    • 5 BR
    • 3 BA
    • Sleeps 8
    2 Reviews
      • 4 BR
      • 3 BA
      • Sleeps 8
      1 Review
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        8
          • 2 BR
          • 2 BA
          • Sleeps 5
          6
            • 5 BR
            • 5 BA
            • 1 HF BA
            • Sleeps 8
            18
              • 1 BR
              • 1 BA
              • Sleeps 2
              8
                • 4 BR
                • 2 BA
                • Sleeps 6
                2 Reviews
                  • 3 BR
                  • 2 BA
                  • Sleeps 6
                    • 3 BR
                    • 1 BA
                    • Sleeps 6
                    7
                      • 3 BR
                      • 2 BA
                      • Sleeps 5
                      26
                        • 9 BR
                        • 3 BA
                        • 1 HF BA
                        • Sleeps 22
                        7
                          • 4 BR
                          • 2 BA
                          • Sleeps 8
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            2 Reviews
                              • 5 BR
                              • 3 BA
                              • Sleeps 10
                              8
                                • 6 BR
                                • 2 BA
                                • 2 HF BA
                                • Sleeps 10
                                4
                                  • 5 BR
                                  • 4 BA
                                  • 1 HF BA
                                  • Sleeps 14
                                  6
                                    • 5 BR
                                    • 2 BA
                                    • 1 HF BA
                                    • Sleeps 12
                                    1 Review
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 10
                                      7
                                        • 3 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 8
                                        9
                                          • 5 BR
                                          • 2 BA
                                          • Sleeps 12
                                          34
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            7
                                              • 4 BR
                                              • 1 BA
                                              • 1 HF BA
                                              • Sleeps 10
                                              • 1 - 22 of 22
                                               

                                              Recent Pittsfield Reviews

                                              Posh Without Pretention

                                              5 of 5
                                              I love your home-- posh without pretense -- comfortable, not fussy, yet every need anticipated and taken care of. The location perfect for music lovers, clean, phone number for help when needed -- a few minor caveats: need grab-bars in showers, broken toilet seat in masterbath.This is my second year renting it; if i can i 'll rent it again.
                                              • Submitted: Aug 14, 2016
                                              • Stayed: Jul 2015

                                              Peaceful country setting

                                              5 of 5
                                              We really enjoyed our visit to the Smith Homestead. Susan is pleasant, helpful, and a wonderful cook. Our continental breakfast included coffee, fruit, juice, and something home baked each day. The room is very comfortable as well. The location is about 15 minutes from Stockbridge (Norman Rockwell and Jonathan Edwards sites). It is also about 20 minutes to Tanglewood and we took in three concerts during our stay.
                                              • Submitted: Jul 12, 2016
                                              • Stayed: Jul 2016

                                              Cozy, charming, Williamstown retreat

                                              5 of 5
                                              What a wonderful little farmhouse. It's cozy, charming, and so Williamstown-y. My friends and I felt right at home. We're Williams alumni, so we particularly appreciated how close the house is to campus. The beds and couches are very comfortable, the kitchen/linen closets/bathrooms have everything you need, and the house is in great shape, but with plenty of character (a claw-footed bathtub!).
                                              • Submitted: Nov 19, 2015
                                              • Stayed: Nov 2015