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Favorite
    • 5 bedrooms
    • 3 bathrooms
    • Sleeps 14
    Favorite
      Viewed 26 times in the last 48 hours
      • 5 bedrooms
      • 3 bathrooms
      • Sleeps 14
      Favorite
        Viewed 9 times in the last 48 hours
        • 3 bedrooms
        • 2 bathrooms
        • Sleeps 10
        Favorite
          Viewed 15 times in the last 48 hours
          • 4 bedrooms
          • 3 bathrooms
          • Sleeps 10
          Favorite
            Viewed 11 times in the last 48 hours
            • 5 bedrooms
            • 3 bathrooms
            • Sleeps 12
            Favorite
              Viewed 6 times in the last 48 hours
              • 3 bedrooms
              • 2 bathrooms
              • Sleeps 8
              Favorite
                • 5 bedrooms
                • 2 bathrooms
                • Sleeps 12
                Favorite
                  Viewed 10 times in the last 48 hours
                  • 3 bedrooms
                  • 2 bathrooms
                  • Sleeps 20
                  Favorite
                    • 3 bedrooms
                    • 1 bathroom
                    • 1 HF BA
                    • Sleeps 8
                    Favorite
                      Viewed 5 times in the last 48 hours
                      • 3 bedrooms
                      • 2 bathrooms
                      • Sleeps 8
                      Favorite
                        Viewed 15 times in the last 48 hours
                        • 3 bedrooms
                        • 2 bathrooms
                        • 1 HF BA
                        • Sleeps 15
                        Favorite
                          • 2 bedrooms
                          • 1 bathroom
                          • Sleeps 8
                          Favorite
                            • 4 bedrooms
                            • 2 bathrooms
                            • Sleeps 11
                            Favorite
                              Viewed 5 times in the last 48 hours
                              • 5 bedrooms
                              • 3 bathrooms
                              • Sleeps 16
                              Favorite
                                • 3 bedrooms
                                • 3 bathrooms
                                • Sleeps 6
                                Favorite
                                  • 4 bedrooms
                                  • 2 bathrooms
                                  • Sleeps 8
                                  Favorite
                                    • 3 bedrooms
                                    • 3 bathrooms
                                    • Sleeps 6
                                    Favorite
                                      • 3 bedrooms
                                      • 2 bathrooms
                                      • Sleeps 20
                                      Favorite
                                        • 4 bedrooms
                                        • 2 bathrooms
                                        • Sleeps 11
                                        Favorite
                                          Viewed 87 times in the last 48 hours
                                          • 2 bedrooms
                                          • 1 bathroom
                                          • 1 HF BA
                                          • Sleeps 5
                                          Favorite
                                            Viewed 15 times in the last 48 hours
                                            • 4 bedrooms
                                            • 2 bathrooms
                                            • Sleeps 10
                                            Favorite
                                              Viewed 43 times in the last 48 hours
                                              • 5 bedrooms
                                              • 2 bathrooms
                                              • 1 HF BA
                                              • Sleeps 13
                                              Favorite
                                                Viewed 23 times in the last 48 hours
                                                • 1 bedroom
                                                • 1 bathroom
                                                • Sleeps 4
                                                Favorite
                                                  Viewed 10 times in the last 48 hours
                                                  • 2 bedrooms
                                                  • 2 bathrooms
                                                  • Sleeps 4
                                                  Favorite
                                                    Viewed 40 times in the last 48 hours
                                                    • 2 bedrooms
                                                    • 1 bathroom
                                                    • Sleeps 4
                                                    Favorite
                                                      Viewed 12 times in the last 48 hours
                                                      • 3 bedrooms
                                                      • 2 bathrooms
                                                      • Sleeps 6
                                                      Favorite
                                                        Viewed 20 times in the last 48 hours
                                                        • 4 bedrooms
                                                        • 2 bathrooms
                                                        • Sleeps 10
                                                        Favorite
                                                          • 2 bedrooms
                                                          • 2 bathrooms
                                                          • Sleeps 6
                                                          Favorite
                                                            Viewed 20 times in the last 48 hours
                                                            • 1 bedroom
                                                            • 1 bathroom
                                                            • Sleeps 4
                                                            Favorite
                                                              Viewed 7 times in the last 48 hours
                                                              • 1 bedroom
                                                              • 1 bathroom
                                                              • Sleeps 4
                                                              Favorite
                                                                Viewed 13 times in the last 48 hours
                                                                • 1 bedroom
                                                                • 1 bathroom
                                                                • Sleeps 4
                                                                Favorite
                                                                  Viewed 21 times in the last 48 hours
                                                                  • 3 bedrooms
                                                                  • 2 bathrooms
                                                                  • Sleeps 8
                                                                  Favorite
                                                                    Viewed 43 times in the last 48 hours
                                                                    • 5 bedrooms
                                                                    • 3 bathrooms
                                                                    • Sleeps 18
                                                                    Favorite
                                                                      Viewed 22 times in the last 48 hours
                                                                      • 2 bedrooms
                                                                      • 1 bathroom
                                                                      • 1 HF BA
                                                                      • Sleeps 6
                                                                      Favorite
                                                                        Viewed 29 times in the last 48 hours
                                                                        • 2 bedrooms
                                                                        • 1 bathroom
                                                                        • Sleeps 4
                                                                        Favorite
                                                                          Viewed 28 times in the last 48 hours
                                                                          • 5 bedrooms
                                                                          • 3 bathrooms
                                                                          • 1 HF BA
                                                                          • Sleeps 13
                                                                          Favorite
                                                                            Viewed 5 times in the last 48 hours
                                                                            • 1 bedroom
                                                                            • 1 bathroom
                                                                            • Sleeps 4
                                                                            Favorite
                                                                              Viewed 26 times in the last 48 hours
                                                                              • 7 bedrooms
                                                                              • 4 bathrooms
                                                                              • Sleeps 24
                                                                              Favorite
                                                                                • 5 bedrooms
                                                                                • 2 bathrooms
                                                                                • Sleeps 6
                                                                                Favorite
                                                                                  Viewed 8 times in the last 48 hours
                                                                                  • 1 bedroom
                                                                                  • 2 bathrooms
                                                                                  • Sleeps 4
                                                                                  Favorite
                                                                                    Viewed 9 times in the last 48 hours
                                                                                    • 1 bedroom
                                                                                    • 1 bathroom
                                                                                    • Sleeps 4
                                                                                    Favorite
                                                                                      Viewed 14 times in the last 48 hours
                                                                                      • 3 bedrooms
                                                                                      • 3 bathrooms
                                                                                      • Sleeps 10
                                                                                      Favorite
                                                                                        Viewed 17 times in the last 48 hours
                                                                                        • 2 bedrooms
                                                                                        • 2 bathrooms
                                                                                        • Sleeps 6
                                                                                        Favorite
                                                                                          Viewed 20 times in the last 48 hours
                                                                                          • 6 bedrooms
                                                                                          • 4 bathrooms
                                                                                          • Sleeps 12
                                                                                          Favorite
                                                                                            Viewed 11 times in the last 48 hours
                                                                                            • 1 bedroom
                                                                                            • 1 bathroom
                                                                                            • Sleeps 4
                                                                                            Favorite
                                                                                              Viewed 30 times in the last 48 hours
                                                                                              • 5 bedrooms
                                                                                              • 2 bathrooms
                                                                                              • Sleeps 15
                                                                                              Favorite
                                                                                                Viewed 14 times in the last 48 hours
                                                                                                • 1 bedroom
                                                                                                • 1 bathroom
                                                                                                • Sleeps 4
                                                                                                Favorite
                                                                                                  Viewed 11 times in the last 48 hours
                                                                                                  • 3 bedrooms
                                                                                                  • 2 bathrooms
                                                                                                  • Sleeps 14
                                                                                                  Favorite
                                                                                                    Viewed 8 times in the last 48 hours
                                                                                                    • 3 bedrooms
                                                                                                    • 1 bathroom
                                                                                                    • Sleeps 8
                                                                                                    Favorite
                                                                                                      Viewed 24 times in the last 48 hours
                                                                                                      • 1 bedroom
                                                                                                      • 1 bathroom
                                                                                                      • Sleeps 4
                                                                                                      • 1 - 50 of 300+

                                                                                                      Pittsfield: Condos, Chalets & More (300+)

                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      Light-filled winter escape

                                                                                                      5 of 5
                                                                                                      We had a magical winter weekend at this beautiful home. The main room fills with light in the morning and looks out on snow covered woods. The house was clearly built with care and is filled with surprises throughout like a hidden piano and detailed cabinetry. Woodstock has plenty to do and see even if you aren't skiing, but I honestly would have been happy just hanging out at the house all weekend. We made use of the sleds we found in the basement and sat in front of the fireplace every second we were home. Can't wait to return! Couldn't recommend more highly.
                                                                                                      • Submitted: Mar 25, 2017
                                                                                                      • Stayed: Mar 2017

                                                                                                      House was as advertized. Loved the hot tub on the deck.

                                                                                                      4 of 5
                                                                                                      We had 2 couples stay there so used the 2 upstairs bedrooms with the queen beds. Both those bedrooms had TVs, and there were 2 more flat screen TVs - one on the main floor and one in the basement. There was one bathroom on each or the 3 floors and enough room to sleep an army (bunk beds in multiple bedrooms). However, I believe it would have been very crowded with anything more than 8 people. The owner was very helpful and easy to work with. We loved the hot tub and there was a great big grill on the deck also.
                                                                                                      • Submitted: Mar 23, 2017
                                                                                                      • Stayed: Mar 2017

                                                                                                      Great

                                                                                                      5 of 5
                                                                                                      super convienient shuttle access, great pool/hot tub area, great skiing
                                                                                                      • Submitted: Mar 23, 2017
                                                                                                      • Stayed: Mar 2017