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Pittsfield: Vacation Rentals (323)

  • 1 - 50 of 323
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • Sleeps 8
    31
      • 1 BR
      • 1 BA
      • Sleeps 4
      21
        • 3 BR
        • 3 BA
        • Sleeps 8
        1 Review
          NEW!
          • 5 BR
          • 3 BA
          • Sleeps 10
          1 Review
            • 5 BR
            • 3 BA
            • 2 HF BA
            • Sleeps 9
              • 3 BR
              • 2 BA
              • Sleeps 12
              26
                • 2 BR
                • 1 BA
                • Sleeps 7
                3
                  Excellent! 4.6/5
                  (12 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  12
                    • 3 BR
                    • 1 BA
                    • Sleeps 6
                    12
                      Exceptional! 5.0/5
                      (7 reviews)
                      avg/night
                      • 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
                              • 4 BR
                              • 3 BA
                              • 1 HF BA
                              • Sleeps 8
                                NEW!
                                • 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
                                        Wonderful! 4.9/5
                                        (11 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        11
                                          • 5 BR
                                          • 3 BA
                                          • 2 HF BA
                                          • Sleeps 12
                                          3
                                            • 5 BR
                                            • 3 BA
                                            • Sleeps 10
                                            2 Reviews
                                              Exceptional! 5.0/5
                                              (6 reviews)
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 6
                                              6
                                                Exceptional! 5.0/5
                                                (11 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 4
                                                11
                                                  NEW!
                                                  • 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
                                                          Wonderful! 4.9/5
                                                          (17 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          17
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            4
                                                              Exceptional! 5.0/5
                                                              (7 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              7
                                                                • 3 BR
                                                                • Sleeps 6
                                                                4
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 10
                                                                    Wonderful! 4.9/5
                                                                    (27 reviews)
                                                                    avg/night
                                                                    • 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
                                                                                Exceptional! 5.0/5
                                                                                (5 reviews)
                                                                                View details for price
                                                                                • 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
                                                                                                Exceptional! 5.0/5
                                                                                                (9 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 7
                                                                                                9
                                                                                                  Wonderful! 4.9/5
                                                                                                  (9 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  9
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 8
                                                                                                    2 Reviews
                                                                                                      NEW!
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 2
                                                                                                      • 1 - 50 of 323
                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      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

                                                                                                      A Sweet, Relaxing Retreat

                                                                                                      5 of 5
                                                                                                      My husband and I and our pre-teen son stayed here very happily for three nights in mid-July. Attractively simple, clean, spacious cottage in a quiet neighborhood. There's a lake across the street with a place to swim (though we swam in lovely Lake Onota, Pittsfield). Between excursions to nearby scenic and cultural spots we slept comfortably, loafed in the house, bought locally grown raspberries and corn — and had fun playing pool! We thank Kim and Joe for offering this delightful vacation spot -- perfect for our needs!
                                                                                                      • Submitted: Jul 30, 2016
                                                                                                      • Stayed: Jul 2016