check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Pittsfield: Cottage Rentals (53)

  • 1 - 50 of 53
Additional fees apply. Taxes may be added.
    • 2 BR
    • 1 BA
    • Sleeps 5
    8
      • 3 BR
      • 1 BA
      • Sleeps 6
      6
        • 1 BR
        • Sleeps 5
        12
          • 2 BR
          • 1 HF BA
          • Sleeps 8
            • 2 BR
            • 1 BA
            • Sleeps 6
            2 Reviews
              • 2 BR
              • 1 BA
              • Sleeps 6
              7
                • 3 BR
                • 1 BA
                • Sleeps 6
                7
                  • 2 BR
                  • 1 BA
                  • Sleeps 5
                  10
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                      • 3 BR
                      • 1 BA
                      • Sleeps 8
                      11
                        • 2 BR
                        • 1 BA
                        • Sleeps 6
                        4
                          • 2 BR
                          • 1 BA
                          • Sleeps 4
                            • 3 BR
                            • 1 BA
                            • Sleeps 6
                            4
                              • 1 BR
                              • 1 BA
                              • Sleeps 2
                              5
                                • 2 BR
                                • 1 BA
                                • Sleeps 6
                                5
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 3
                                  16
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 6
                                    11
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 5
                                      5
                                        • 3 BR
                                        • 1 BA
                                        • Sleeps 7
                                        29
                                          • 4 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 8
                                          1 Review
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 7
                                            2 Reviews
                                              • 3 BR
                                              • 1 BA
                                              • 1 HF BA
                                              • Sleeps 9
                                              4
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                4
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  3
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    17
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                      2 Reviews
                                                        • 5 BR
                                                        • 1 BA
                                                        • 1 HF BA
                                                        • Sleeps 9
                                                        2 Reviews
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          5
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            2 Reviews
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 9
                                                              4
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 5
                                                                  12
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 6
                                                                      • 3 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 12
                                                                        1 Review
                                                                          • 2 BR
                                                                          • Sleeps 6
                                                                          23
                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            4
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              13
                                                                                • 3 BR
                                                                                • 1 BA
                                                                                • Sleeps 8
                                                                                9
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 5
                                                                                  13
                                                                                    View details for price
                                                                                    • 3 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    2 Reviews
                                                                                      • 5 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 14
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 5
                                                                                        16
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 6
                                                                                          14
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 9
                                                                                              • 3 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              7
                                                                                                • 3 BR
                                                                                                • 1 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 6
                                                                                                5
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  9
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 6
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 6
                                                                                                      1 Review
                                                                                                      • 1 - 50 of 53
                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      Quiet Camp On A Small Pond

                                                                                                      4 of 5
                                                                                                      If you're a family looking for a quiet retreat but don't mind close neighbors this is for you. If you want absolute quiet and privacy this may not be the place for you. Otherwise it is clean and you have everything you need including the awesome dock and good fishing. Really nothing negative to say and the owners were easy to deal with and very nice.
                                                                                                      • Submitted: Sep 23, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      wonderful home on the lake

                                                                                                      5 of 5
                                                                                                      We had an amazing time at this house. It was a mini family reunion. This was the perfect place From being able to fit us all in and never feeling crowded to the beautiful deck where we ate most of our meals plus a few feet away you are in the lake we kayaked , paddle boarded, and swam on this breath taking lake The owners of the home could not have been friendlier and I had been in contact with them several times for info about places to eat etc ... We almost wanted to not give this review as we wanted to keep this gem of a home to our selves :) we plan on having this an annual vacation and wouldn't change a thing !
                                                                                                      • Submitted: Sep 15, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Labor Day At Winnie

                                                                                                      5 of 5
                                                                                                      What was not to like? the Weather was good the place was nice and clean. did not catch any Salmon though. Also got to go to Wolfboro by boat.
                                                                                                      • Submitted: Sep 9, 2016
                                                                                                      • Stayed: Sep 2016