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 svg-report-flag
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 (50)

  • 1 - 50 of 50
Additional fees apply. Taxes may be added.
    Excellent! 4.4/5
    (14 reviews)
    avg/night
    • 3 BR
    • 1 BA
    • Sleeps 6
    Cottage #203288vb
    14
    Viewed 19 times in the last 48 hours
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 7
      Cottage #310698
      6
      Viewed 10 times in the last 48 hours
        avg/night
        • 5 BR
        • 3 BA
        • Sleeps 8
        Cottage #425380vb
        2 Reviews
        Viewed 35 times in the last 48 hours
          Wonderful! 4.9/5
          (17 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 6
          Cottage #300900
          17
          Viewed 21 times in the last 48 hours
            Wonderful! 4.8/5
            (37 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 6
            Cottage #293009
            37
            Viewed 33 times in the last 48 hours
              • 2 BR
              • 1 BA
              • Sleeps 4
              Cottage #587561vb
              3
                • 2 BR
                • 2 BA
                • Sleeps 6
                Cottage #3790476
                9
                  Wonderful! 4.9/5
                  (18 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 5
                  Cottage #707780vb
                  18
                  Viewed 26 times in the last 48 hours
                    Wonderful! 4.9/5
                    (16 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    Cottage #13495vb
                    16
                    Viewed 16 times in the last 48 hours
                      Excellent! 4.7/5
                      (23 reviews)
                      avg/night
                      • 2 BR
                      • 1 BA
                      • Sleeps 5
                      Cottage #3624808
                      23
                      Viewed 9 times in the last 48 hours
                        Wonderful! 4.9/5
                        (20 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 6
                        Cottage #980198
                        20
                        Viewed 20 times in the last 48 hours
                          Wonderful! 4.9/5
                          (9 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          Cottage #554803vb
                          9
                          Viewed 14 times in the last 48 hours
                            • 3 BR
                            • 1 BA
                            • Sleeps 5
                            Cottage #4270922
                            2 Reviews
                            Viewed 14 times in the last 48 hours
                              • 2 BR
                              • 1 BA
                              • Sleeps 6
                              Cottage #876320vb
                              3
                              Viewed 14 times in the last 48 hours
                                Excellent! 4.6/5
                                (10 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 6
                                Cottage #747467vb
                                10
                                Viewed 7 times in the last 48 hours
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 8
                                  Cottage #3576605
                                  10
                                    Wonderful! 4.9/5
                                    (10 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 6
                                    Cottage #361931vb
                                    10
                                    Viewed 12 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (6 reviews)
                                      avg/night
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 6
                                      Cottage #4231093
                                      6
                                      Viewed 10 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (25 reviews)
                                        avg/night
                                        • Studio
                                        • 1 BA
                                        • Sleeps 2
                                        Cottage #571465vb
                                        25
                                        Viewed 9 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (11 reviews)
                                          avg/night
                                          • 4 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 7
                                          Cottage #479116vb
                                          11
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Cottage #872747vb
                                            3
                                            Viewed 14 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (13 reviews)
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Cottage #962761
                                              13
                                              Viewed 8 times in the last 48 hours
                                                • 3 BR
                                                • 1 BA
                                                • Sleeps 4
                                                Cottage #865112vb
                                                1 Review
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  Cottage #3755600
                                                  4
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Cottage #709006vb
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 2
                                                      Cottage #4294951
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Cottage #702529vb
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 6
                                                          Cottage #663462vb
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            Cottage #367222vb
                                                            Viewed 7 times in the last 48 hours
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              Cottage #7079868
                                                                • 2 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 7
                                                                Cottage #835252vb
                                                                Viewed 12 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (14 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 7
                                                                  Cottage #3023396
                                                                  14
                                                                  Viewed 12 times in the last 48 hours
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 6
                                                                    Cottage #479807vb
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Cottage #372576vb
                                                                      3
                                                                      Viewed 27 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (9 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 8
                                                                        Cottage #478242vb
                                                                        9
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 6
                                                                          Cottage #230835
                                                                          4
                                                                          Viewed 5 times in the last 48 hours
                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • Sleeps 7
                                                                            Cottage #3680979
                                                                            1 Review
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Cottage #701496vb
                                                                                Exceptional! 5.0/5
                                                                                (8 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 1 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 7
                                                                                Cottage #399366vb
                                                                                8
                                                                                  Excellent! 4.4/5
                                                                                  (10 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 4
                                                                                  Cottage #157193
                                                                                  10
                                                                                  Viewed 6 times in the last 48 hours
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 2
                                                                                    Cottage #463468vb
                                                                                    4
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      Cottage #428792vb
                                                                                      1 Review
                                                                                        • 3 BR
                                                                                        • 1 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 6
                                                                                        Cottage #101846
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 6
                                                                                          Cottage #3593630
                                                                                            Exceptional! 5.0/5
                                                                                            (10 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 6
                                                                                            Cottage #230313
                                                                                            10
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Cottage #254020vb
                                                                                              24
                                                                                                • 3 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Cottage #3603336
                                                                                                6
                                                                                                  Exceptional! 5.0/5
                                                                                                  (6 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                  Cottage #746021vb
                                                                                                  6
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 5
                                                                                                    Cottage #297720vb
                                                                                                    • 1 - 50 of 50
                                                                                                     

                                                                                                    Recent Pittsfield Reviews

                                                                                                    Lovely!

                                                                                                    5 of 5
                                                                                                    What a warm and charming cottage! The location is extremely convenient. Ruth and Gareth were very welcoming. We will stay agian.
                                                                                                    • Submitted: Dec 1, 2016
                                                                                                    • Stayed: Nov 2016

                                                                                                    It was a wonderful weekend getaway.

                                                                                                    4 of 5
                                                                                                    Djuna has a clean, welcoming home. It was spacious and had the necessary equipment for my weekend trip with 3 other people. I wish the heat was controllable by the us and not the owner. Besides that the communication between Djuna was minimal. Once in contact with her, she was flexible and nice. I'd consider returning back to the property in the summer. Thanks for renting out your space!
                                                                                                    • Submitted: Nov 30, 2016
                                                                                                    • Stayed: Nov 2016

                                                                                                    Extremely cozy and wonderful host

                                                                                                    5 of 5
                                                                                                    My group had a wonderful weekend at the Jeffers Cottage! Scott met with us when we first arrived to show us the house and how everything worked as well answer any questions we had! We went in the fall and with the neighborhood being mostly summer homes we had the whole place to ourselves! The house is fully equipped with everything you need. No Wifi but we wanted a weekend off the grid. A 2 minute walk to the lake in Scott's pictures. Scott was easy to contact for anything we needed and gave us lots of info of things to do in the area (The Quarry hike was awesome!) Overall a beautiful weekend in the Berkshires!!!
                                                                                                    • Submitted: Nov 28, 2016
                                                                                                    • Stayed: Nov 2016