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Pittsfield: Houses, Cottages & More (467)

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Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
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    30
      • 1 BR
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      21
        • 1 BR
        • 1 BA
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        9
          • 2 BR
          • 1 BA
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          3
            • 5 BR
            • 3 BA
            • 2 HF BA
            • Sleeps 9
              • 3 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 9
              7
                NEW!
                • 3 BR
                • 3 BA
                • Sleeps 8
                1 Review
                  • 4 BR
                  • 3 BA
                  • 1 HF BA
                  • Sleeps 12
                  3
                    • 3 BR
                    • 1 BA
                    • Sleeps 6
                    12
                      • 3 BR
                      • 2 BA
                      • Sleeps 12
                      26
                        • 5 BR
                        • 3 BA
                        • Sleeps 8
                        2 Reviews
                          • 2 BR
                          • 1 BA
                          • Sleeps 4
                          4
                            • 3 BR
                            • 2 BA
                            • Sleeps 7
                            6
                              NEW!
                              • 4 BR
                              • 3 BA
                              • 1 HF BA
                              • Sleeps 8
                                NEW!
                                • 3 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 5
                                  • 7 BR
                                  • 3 BA
                                  • Sleeps 18
                                  22
                                    NEW!
                                    • 5 BR
                                    • 3 BA
                                    • Sleeps 10
                                      • 1 BR
                                      • 1 BA
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                                      10
                                        • 5 BR
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                                        • 2 HF BA
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                                        3
                                          NEW!
                                          • 2 BR
                                          • 2 BA
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                                          4
                                            NEW!
                                            • 5 BR
                                            • 3 BA
                                            • Sleeps 10
                                            2 Reviews
                                              • 3 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 6
                                              5
                                                • 2 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 4
                                                11
                                                  NEW!
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                                                  • 2 BA
                                                  • Sleeps 8
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                                                    • 2 BA
                                                    • Sleeps 6
                                                    3
                                                      NEW!
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 5
                                                      2 Reviews
                                                        NEW!
                                                        • 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
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                                                                        5
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                            NEW!
                                                                            • 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
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                                                                                      3
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        6
                                                                                          NEW!
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                            11
                                                                                              • 5 BR
                                                                                              • 5 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 10
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 7
                                                                                                  9
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 6
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
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                                                                                                      • 1 - 50 of 467
                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      It's a no brainier! This is a gem in the woods!

                                                                                                      5 of 5
                                                                                                      We love this cabin! This is such a great little retreat in the woods. It's private, quiet, and peaceful. We love the upper sitting area with the record player and full length Windows that over look the pines. Having a full kitchen and grill is a great way to stay in and enjoy the house. I suggest eating on the deck or enjoy a morning cup of coffee on the deck is quiet and relaxing. Beautiful trails at the Audubon and Kennedy park are right down the street, and when you're done for the day you can soak in the spacious hot tub or nap in the hammock. It's a great little spot that's unique and welcoming. The beds are amazingly comfortable and waking up with all the windows brings the outdoors inside. We can't wait to come back!!
                                                                                                      • Submitted: Aug 29, 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