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  • Showing 1-50 of 223
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    Wonderful! 4.9/5
    (36 reviews)
    avg/night
    • 3 BR
    • 1 BA
    • Sleeps 6
    House #469617vb
    36
    Viewed 25 times in the last 48 hours
      Wonderful! 4.9/5
      (27 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 12
      House #420727vb
      27
      Viewed 18 times in the last 48 hours
        Very Good! 4.0/5
        (8 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 7
        House #344576vb
        8
        Viewed 32 times in the last 48 hours
          Wonderful! 4.8/5
          (23 reviews)
          avg/night
          • 1 BR
          • 1 BA
          • Sleeps 4
          House #310035vb
          23
          Viewed 18 times in the last 48 hours
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 6
            House #4113926
            1
            Viewed 5 times in the last 48 hours
              avg/night
              • 8 BR
              • 5 BA
              • Sleeps 20
              House #985738vb
              0
              Viewed 12 times in the last 48 hours
                Exceptional! 5.0/5
                (6 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 6
                House #804956vb
                6
                Viewed 16 times in the last 48 hours
                  Wonderful! 4.9/5
                  (9 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 7
                  House #330190
                  9
                  Viewed 13 times in the last 48 hours
                    Wonderful! 4.9/5
                    (23 reviews)
                    avg/night
                    • 5 BR
                    • 5 BA
                    • Sleeps 12
                    House #729783vb
                    23
                    Viewed 27 times in the last 48 hours
                      Wonderful! 4.8/5
                      (18 reviews)
                      avg/night
                      • 3 BR
                      • 3 BA
                      • 1 HF BA
                      • Sleeps 10
                      House #272149vb
                      18
                      Viewed 36 times in the last 48 hours
                        Exceptional! 5.0/5
                        (16 reviews)
                        avg/night
                        • 3 BR
                        • 1 BA
                        • 1 HF BA
                        • Sleeps 8
                        House #3811779
                        16
                        Viewed 19 times in the last 48 hours
                          Exceptional! 5.0/5
                          (10 reviews)
                          avg/night
                          • 6 BR
                          • 3 BA
                          • Sleeps 10
                          House #4064007
                          10
                          Viewed 35 times in the last 48 hours
                            Wonderful! 4.9/5
                            (17 reviews)
                            avg/night
                            • 5 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 12
                            House #561543vb
                            17
                            Viewed 14 times in the last 48 hours
                              Exceptional! 5.0/5
                              (10 reviews)
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Sleeps 8
                              House #4193492
                              10
                              Viewed 26 times in the last 48 hours
                                Exceptional! 5.0/5
                                (16 reviews)
                                avg/night
                                • 4 BR
                                • 3 BA
                                • 1 HF BA
                                • Sleeps 12
                                House #583082vb
                                16
                                Viewed 41 times in the last 48 hours
                                  avg/night
                                  • 4 BR
                                  • 2 BA
                                  • 1 HF BA
                                  • Sleeps 8
                                  House #4222851
                                  0
                                  Viewed 6 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (32 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 3
                                    House #135474vb
                                    32
                                    Viewed 21 times in the last 48 hours
                                      Exceptional! 5.0/5
                                      (20 reviews)
                                      avg/night
                                      • 3 BR
                                      • 3 BA
                                      • Sleeps 8
                                      House #224680
                                      20
                                      Viewed 57 times in the last 48 hours
                                        Excellent! 4.4/5
                                        (12 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 4
                                        House #3860654
                                        12
                                        Viewed 25 times in the last 48 hours
                                          Exceptional! 5.0/5
                                          (16 reviews)
                                          avg/night
                                          • 6 BR
                                          • 5 BA
                                          • 1 HF BA
                                          • Sleeps 16
                                          House #396147vb
                                          16
                                          Viewed 45 times in the last 48 hours
                                            Excellent! 4.6/5
                                            (21 reviews)
                                            avg/night
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 10
                                            House #283894vb
                                            21
                                            Viewed 28 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (5 reviews)
                                              avg/night
                                              • 5 BR
                                              • 3 BA
                                              • Sleeps 8
                                              House #4160350
                                              5
                                              Viewed 12 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (14 reviews)
                                                avg/night
                                                • 5 BR
                                                • 3 BA
                                                • Sleeps 10
                                                House #603552vb
                                                14
                                                Viewed 21 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (15 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  House #3720156
                                                  15
                                                  Viewed 22 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (10 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 4 BA
                                                    • 1 HF BA
                                                    • Sleeps 12
                                                    House #4050256
                                                    10
                                                    Viewed 30 times in the last 48 hours
                                                      Excellent! 4.7/5
                                                      (27 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      House #419897vb
                                                      27
                                                      Viewed 19 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (9 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • 1 HF BA
                                                        • Sleeps 8
                                                        House #854910vb
                                                        9
                                                        Viewed 14 times in the last 48 hours
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 10
                                                          House #471272vb
                                                          0
                                                          Viewed 7 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (8 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 6
                                                            House #4153058
                                                            8
                                                            Viewed 6 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (9 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              House #892478vb
                                                              9
                                                              Viewed 51 times in the last 48 hours
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                House #570547vb
                                                                3
                                                                Viewed 10 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (7 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 8
                                                                  House #585864vb
                                                                  7
                                                                  Viewed 40 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (8 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 6
                                                                    House #4155013
                                                                    8
                                                                    Viewed 13 times in the last 48 hours
                                                                      Excellent! 4.6/5
                                                                      (12 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 7
                                                                      House #479396vb
                                                                      12
                                                                      Viewed 40 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (16 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 10
                                                                        House #601571vb
                                                                        16
                                                                        Viewed 30 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (19 reviews)
                                                                          avg/night
                                                                          • 5 BR
                                                                          • 3 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 15
                                                                          House #660967vb
                                                                          19
                                                                          Viewed 38 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (17 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            House #3893831
                                                                            17
                                                                            Viewed 11 times in the last 48 hours
                                                                              Excellent! 4.7/5
                                                                              (18 reviews)
                                                                              avg/night
                                                                              • 9 BR
                                                                              • 4 BA
                                                                              • Sleeps 20
                                                                              House #428459vb
                                                                              18
                                                                              Viewed 126 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (39 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                House #3721423
                                                                                39
                                                                                Viewed 29 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (9 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 7
                                                                                  House #701122vb
                                                                                  9
                                                                                  Viewed 19 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (10 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 6
                                                                                    House #693973vb
                                                                                    10
                                                                                    Viewed 11 times in the last 48 hours
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 11
                                                                                      House #702723vb
                                                                                      3
                                                                                      Viewed 9 times in the last 48 hours
                                                                                        • 5 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 10
                                                                                        House #3959837
                                                                                        12
                                                                                        Viewed 45 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (10 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          House #765436vb
                                                                                          10
                                                                                          Viewed 13 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (11 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 10
                                                                                            House #580955vb
                                                                                            11
                                                                                            Viewed 18 times in the last 48 hours
                                                                                              • 3 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 6
                                                                                              House #4221107
                                                                                              13
                                                                                              Viewed 40 times in the last 48 hours
                                                                                                Excellent! 4.6/5
                                                                                                (11 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 1 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 8
                                                                                                House #467696vb
                                                                                                11
                                                                                                Viewed 17 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (29 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 8
                                                                                                  House #580967vb
                                                                                                  29
                                                                                                  Viewed 16 times in the last 48 hours
                                                                                                    Wonderful! 4.8/5
                                                                                                    (19 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    House #236935vb
                                                                                                    19
                                                                                                    Viewed 14 times in the last 48 hours
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 8
                                                                                                      House #705514vb
                                                                                                      1
                                                                                                      Viewed 17 times in the last 48 hours
                                                                                                      • 1 - 50 of 223

                                                                                                      Pittsfield: House Rentals (223)

                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      Perfect getaway!

                                                                                                      5 of 5
                                                                                                      Our group of 6 adults and 1 infant enjoyed our time at the Grey House over MLK weekend. The house is perfectly located, just 2.5 hours from NYC and Boston, for us to meet. Ed has decorated the place with beautiful furniture and art work from their travels in Europe. There are many houses in the area for rent, but the Grey House is just perfect for us with the decor, layout, and comfort. The house is also stocked with everything we needed including a fully functional kitchen, many extra towels, and sheets. Our group made use the kitchen and big dinning table for many lunches and dinners. Thank you for opening the house to us and we highly recommend the fabulous Grey House for your next Berkshire/Hudson Valley trip.
                                                                                                      • Submitted: Jan 17, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      Lovely weekend getaway

                                                                                                      5 of 5
                                                                                                      This is a lovely house and was perfect for 5 adults. The house is rustic and situated in a remote, beautiful part of the Berkshires, yet close to Stockbridge, the Norman Rockwell museum and other sites. It was toasty warm and we had a warm fire in the cozy living room at night. The house was very clean and the owners give you lots of information about the local area to help plan your stay. We will definitely visit again.
                                                                                                      • Submitted: Jan 16, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      Beautiful property in charming town with wonderful manager

                                                                                                      5 of 5
                                                                                                      I came to stay at the South Lee Schoolhouse to celebrate New Year's Eve and had a wonderful time there. I visited with a party of 6, though there is easily space for a few more. The house is gorgeous with tall ceilings and open spaces. It had available everything we needed, including a fully stocked (and beautiful) kitchen for cooking full meals at home. There is also wood available for a cozy fire in winter. The house has a scenic view, is easy to locate, and is only a short drive from downtown Stockbridge. The owner, Mary, is great. She is easily available if any questions come up, and is very responsive if you should need anything. She really went above and beyond in making our stay happy and smooth. Finally, the area is scenic and filled with great things to do. Since we visited in winter, we went snow shoeing at Hilltop Orchards, for a sleigh ride at SweetBrook Farm, and really enjoyed the hot chocolate menu at the Blantyre. We also loved the Norman Rockwell museum and the Clark Institute. Plus, walking around downtown Stockbridge finds iconic settings and fun shops. Altogether a great stay!
                                                                                                      • Submitted: Jan 15, 2017
                                                                                                      • Stayed: Dec 2016